The Roundabout Route and The Road Not Traveled/2

The Roundabout Route and The Road Not Traveled

Exegetical Approaches

Overview

Some of the most formative events in the history of the Children of Israel occurred on the Wilderness Route, and it is difficult to imagine how history would have evolved without them.  However, the sublime benefits of this travel route are more obvious only in retrospect, while the Torah appears to explain its choice by highlighting the more mundane dangers associated with the alternative Philistine Route.  Commentators thus struggle with how to reconcile the relationship between what we know to be important and what the text says, with their positions partially dependent on whether baiting Paroh into chasing after the Israelites was a crucial element of the Divine master plan.

Two approaches emphasize the advantages of the Wilderness Route.  R"Y Bekhor Shor and Sforno focus exclusively on the immediate objective of reaching Yam Suf, saying that this was always Hashem's initial plan and that this alone accounts for the path taken.  The Mekhilta and many others also accent the positive, but they instead stress the long range benefits of traveling through the wilderness, as it allowed the nation to acquire the mental, physical, and spiritual fortitude needed to conquer and settle Canaan.  In contrast to both of these positions, Rashi and others adopt the simple reading of the text that the purpose was merely to avoid the pitfalls of the alternative Philistine Route.  Finally, Akeidat Yitzchak and Abarbanel attempt to synthesize various approaches, combining the mundane reasoning explicit in the text with the more implicit transcendent motives.

The following is an analysis of the spectrum of approaches regarding Hashem's main objective in leading the Israelites by way of the Wilderness Route:

Facilitating the Egyptians' Destruction

The Wilderness Route was selected in order to ensure a confrontation in which the Egyptians would drown in the Sea (the primary purpose is indicated in the words "יַם סוּף").  This would sever the Israelites' remaining bonds of servitude, thereby enabling them to then (and only then) proceed to Israel.

Sources:R. Yosef Bekhor ShorShemot 13:17-18Shemot 14:2-4About R. Yosef Bekhor Shor, SfornoShemot 13:17-18Shemot 14:5Shemot 14:30About R. Ovadyah Sforno¹

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? R"Y Bekhor Shor and Sforno assume that Paroh had been led to believe that the Israelites intended to return to slavery after their holiday, and had sent them away only temporarily (see A Three Day Journey).²  Thus, regardless of the route taken, once Paroh would realize that his slaves were not returning of their own volition, it was inevitable that he would chase after them.³

Was the Splitting of the Sea preordained? Since Paroh was going to pursue the Israelites, the need to drown the Egyptians at Yam Suf was unavoidable.⁴  Otherwise, the Israelites would have been forced to return to Egyptian bondage.⁵

"וְלֹא נָחָם אֱ-לֹהִים...‏ כִּי קָרוֹב הוּא" – Where is the Israelites' destination?

• Yam Suf – Sforno contends that heading for Israel was not even a consideration prior to the drowning of the Egyptians at Yam Suf, as it was still assumed that the Israelites were returning to Egypt.  Accordingly, the verse cannot be speaking of which path was the shortest to Israel, but must rather be dealing with which was the quickest to Yam Suf.⁶  He thus posits that each of the Philistine Route and the Wilderness Route must have led to Yam Suf,⁷ but that the Philistine Route was the shorter one of the two.⁸
• Israel – R"Y Bekhor Shor, though, does assume that the verse is speaking of which path the nation was to take to arrive in the land of Israel.⁹  He explains that the Philistine Route was the shortest option¹⁰ and would have been the obvious choice had the Egyptian threat not existed.¹¹  According to him, this is precisely what the verses are saying – Yam Suf needed to occur and the Egyptian army needed to be disposed of before the Israelites could journey to Canaan.¹²

"בִּרְאֹתָם מִלְחָמָה" – Concern over war with whom?

• With Egypt and the Philistines – According to R"Y Bekhor Shor, Hashem's immediate concern was about the Israelites' potentially fearful response to being surrounded by foes, as they would be attacked by the pursuing Egyptians from behind as well as the looming Philistine threat from the front.¹³
  
• With Egypt alone – Sforno similarly contends that the Divine concern was that the Israelites might panic upon hearing¹⁴ that the Egyptians were in hot pursuit and return to Egypt rather than fight.  Sforno, though, assumes that this encounter would occur even before the Israelites reached Philistine territory.¹⁵

How does the Wilderness Route provide the solution? According to both of these commentators, the Wilderness Route was not chosen to avoid a confrontation with the Egyptian enemy.  In fact, such an encounter was not only unavoidable, but also desirable, as it would result in the drowning of the Egyptian masters and the termination of the Israelites' slavery.¹⁶  The goal of the selected route was merely to avert the possibility that the Israelites would panic and flee back to Egypt before the Egyptians were eliminated.

• Avoiding a dual front battle – R"Y Bekhor Shor explains that traveling via the Wilderness Route avoided exposing the Israelites to a two-pronged attack.¹⁷
• Forcing a confrontation – Sforno posits that the Wilderness Route was chosen since it was devoid of spies and informers.  As such, the Israelites would be unaware of the pursuing Egyptians until it was too late to flee.¹⁸

"דֶּרֶךְ הַמִּדְבָּר יַם סוּף" – This approach emphasizes, not the wilderness aspect of the chosen route ("דֶּרֶךְ הַמִּדְבָּר"), but that it led to Yam Suf ("‏יַם סוּף‏‏"‎).¹⁹  The miracle of Yam Suf was Hashem's ultimate objective, and the raison d'être for this leg of the journey rather than merely its consequence.

Double "כִּי"

• Two opposing factors – R"Y Bekhor Shor understands the "כִּי" of "כִּי קָרוֹב הוּא" to be providing the reason why the Philistine Route might have been chosen,²⁰ while only the "כִּי" of "כִּי אָמַר אֱ-לֹהִים" explains why this option was rejected.
• Two parts of the same explanation – According to Sforno, both "כִּי" phrases constitute part of the reason for not choosing the Philistine Route.²¹

"וְשָׁבוּ מִצְרָיְמָה" – R"Y Bekhor Shor and Sforno understand the phrase to refer to the fear lest the nation physically return to Egypt and its bondage.²²

"וַחֲמֻשִׁים" – R"Y Bekhor Shor understands the verse to refer to food provisions and to be clarifying that the Israelites were well supplied enough to take the longer route through the wilderness. Sforno, in contrast, understands it to refer to military arms and suggests that the verse is highlighting that despite being armed, the nation lacked the courage to fight their masters.

Was the objective of the Wilderness Route achieved and when? According to this approach, traveling via the Wilderness Route succeeded in ensuring that the Egyptians drowned at Yam Suf and in permanently casting off the Egyptian yoke of slavery.²³  This though raises the question of why the Israelites did not take the Philistine Route once Yam Suf had already occurred and accomplished its goal.²⁴

What about Sinai? Sforno asserts that Mt. Sinai was always meant to be the second stop; first, though, Hashem wanted to drown the Egyptians.

Biblical parallels – Sforno compares Hashem's plan here to the words of Devorah to Barak in Shofetim 4:7, "וּמָשַׁכְתִּי אֵלֶיךָ אֶל נַחַל קִישׁוֹן אֶת סִיסְרָא".  There, too, Hashem drew the enemy to a particular place with intent to drown its chariots and wipe out its army.²⁵

Affording Opportunities for National Growth

The Wilderness Route was not just the default alternative to a rejected route, but rather had value in its own right (the key words being "דֶּרֶךְ הַמִּדְבָּר"), as it offered the nation vital opportunities that the Philistine Route could not. This approach subdivides regarding what this route had to offer:

Physical and Mental Fortitude

The Wilderness Route afforded the nation both the time and environment needed to discard their slave mentality and gain the confidence and independence essential to conquer and rule Canaan.

Sources:R. Eliezer in Mekhilta DeRabbi YishmaelBeshalach VayehiAbout Mekhilta DeRabbi Yishmael, Various opinions in Shemot Rabbah20:11-16About Shemot Rabbah, R. Saadia GaonShemot 13:18About R. Saadia Gaon, RambamGuide to the Perplexed 3:24Guide to the Perplexed 3:32About R. Moshe b. Maimon, Shadal #1Shemot 13:17-18About R. Shemuel David Luzzatto, R. S"R HirschShemot 13:17-18About R. Samson Raphael Hirsch, MalbimShemot 13:17-18About R. Meir Leibush Weiser,²⁶ R. D"Z HoffmannShemot 13:17-18About R. David Zvi Hoffmann, U. CassutoShemot 13:17-18About Prof. Umberto Cassuto

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? This approach works simplest for those who posit that Paroh had already permanently freed the Israelites,²⁷ and that thus the drowning of the Egyptians at Yam Suf was neither necessary as a prerequisite for entrance into Canaan nor inevitable.

Introduction for long range goals rather than short term decision – Those who maintain that the Israelites were initially released for only a three day journey²⁸ must grapple with the question of why the immediate Egyptian threat and the need for Yam Suf are not mentioned as factors in the selection of the route.²⁹  They could explain that our verses are presenting Hashem's reasoning not for merely the short term decision to opt for the Wilderness Route until the events of Yam Suf, but also for why the Israelites continued on it even after the Egyptian threat had already been eliminated.³⁰

"וְלֹא נָחָם אֱ-לֹהִים... כִּי קָרוֹב הוּא" – Close to where and what was the concern? These commentators assume that the verse is speaking of the route to Canaan and that the problematic issue is the shortness of the Philistine Route to Canaan, as expressed in the words "כִּי קָרוֹב הוּא"‎.³¹  The result would have been that the Children of Israel would have arrived almost immediately in Canaan and been forced to fight the wars of conquest before they were physically and mentally prepared for them.

"בִּרְאֹתָם מִלְחָמָה" – Avoiding war with whom? The wars to be avoided for the immediate future were the battles of the conquest of Canaan.

How does the Wilderness Route solve the problem and when?

• Growth through trials – Rambam emphasizes how the scarcity and hardships of wilderness life instilled courage and strength,³² and he explains that this was the purpose of the trials (נסיונות) in the wilderness.³³  R. Hirsch adds that the challenges encountered taught them to trust in Hashem, which, in turn, gave them the self-confidence needed to fight. Shadal further asserts that the time in the wilderness provided time to learn the skills necessary for self rule.
• New generation – Rambam proposes that the forty years in the wilderness meant that it was a new generation that had never been enslaved which entered the land.³⁴ This generation was not encumbered by a slave mentality, and was thus more capable of dealing with the challenges of conquest and government.³⁵  Rambam's dim view of the generation of the Exodus is reflected also in his contention that numerous commandments needed to be given to address its deficiencies.³⁶
• Miracles as morale booster – Malbim maintains that the splitting of the sea and other miracles of the wilderness would both instill fear in the Canaanites³⁷ and boost the belief, and hence the courage, of the Israelites enabling a victory over their enemies.
• Stalling for the Canaanites – Malbim³⁸ adds that the extra time afforded by the Wilderness Route ensured that the sins of the Emorites would be complete and they would deserve to be eliminated by the time the Israelites arrived in the land.³⁹

Physical vs. Spiritual – This approach assumes that the conquest of Canaan would require human strength and courage, and not be completely supernatural.⁴⁰

Later desires to return to Egypt – The Mekhilta notes that the nation's later desires (even on the longer route) to return to Egypt ("נִתְּנָה רֹאשׁ וְנָשׁוּבָה מִצְרָיְמָה") prove that had they gone the shorter route and been forced to fight the Canaanites they would surely have fled back to Egypt.⁴¹  On the Wilderness Route, although there were periodic grumblings to head back to Egypt, these were never acted upon.

Parallels to the Sin of the Spies and the need for forty years – This approach could understand the decree after the Sin of the Spies in a similar fashion.  Through their sin, the nation demonstrated that they did not possess the requisite courage to conquer, and thus more time needed to elapse before they could enter the land of Israel.⁴²  In this case also, the nation's unpreparedness and cowardice force the postponement of the entry into the Promised Land and the need to detour so as to find a less daunting point of entry.

Where is "דֶּרֶךְ אֶרֶץ פְּלִשְׁתִּים"? Most of these commentators do not explicitly address this issue, but most⁴³ likely assume that it refers to the coastal route (also known as "דֶּרֶךְ הַיָּם") that leads northeast out of Egypt, traversing the Philistine cities of Ashkelon and Ashdod, on the shores of the Mediterranean Sea.  At the time of the Exodus, though, the Philistines who later live in this area had not yet arrived,⁴⁴ leading Cassuto to assert that the verse instead refers to the way that leads from Egypt to Israel via the Negev,⁴⁵ which was home to the Philistines of Avraham's time.⁴⁶

Double "כִּי" – According to these commentators, both appearances of the word mean "because", and the two provided reasons work together to explain why the Philistine Route was not chosen. Although one might have thought that a quick route would be advantageous, in this case it constitutes a problem. If the nation was forced to wage war against the Canaanites so soon after being freed, before they were battle ready, they would inevitably opt to return to servitude in Egypt.

"וַחֲמֻשִׁים" – Shadal asserts that the verses point this fact out to highlight that it was not due to lack of weaponry that the nation would flee, but rather because of their lack of courage.

What about Sinai? R. D"Z Hoffmann asserts that there was nothing so unique about Mt. Sinai, and had they taken a different route Hashem would have simply chosen a different site for revelation. It was only because Hashem knew in advance which path the nation was to travel that He had previously told Moshe that the nation would serve him at Sinai.

Spiritual Development

The trek through the wilderness enabled the nation to receive the Torah at Mt. Sinai and/or witness many other miracles, thereby deepening their belief in and religious connection to Hashem and His ways.

Sources:R. Yehoshua in Mekhilta DeRabbi YishmaelBeshalach VayehiAbout Mekhilta DeRabbi Yishmael, opinions in Shemot Rabbah20:11-16About Shemot Rabbah, R. ChananelCited by R. Bachya Shemot 13:17About R. Chananel b. Chushiel, perhaps RashbamShemot 13:17-18Shemot 16:4About R. Shemuel b. Meir,⁴⁷ Toledot YitzchakShemot 13:17-18About R. Yitzchak Karo, Keli YekarShemot 13:17About R. Shelomo Ephraim Lunshitz, Shadal #2Shemot 13:17-18About R. Shemuel David Luzzatto, R. S"R Hirsch, MalbimShemot 13:17-18About R. Meir Leibush Weiser,⁴⁸ NetzivShemot 13:17-18About R. Naftali Z"Y Berlin, Meshekh ChokhmahShemot 13:17-18About R. Meir Simcha of Dvinsk

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? This approach works simplest for those who posit that Paroh had already permanently freed the Israelites,⁴⁹ and that thus the drowning of the Egyptians at Yam Suf was neither necessary as a prerequisite for entrance into Canaan nor inevitable.⁵⁰

Introduction for long range goals rather than short term decision – Those who maintain that the Israelites were initially released for only a three day journey⁵¹ must explain why the immediate Egyptian threat and the need for Yam Suf are not mentioned as factors in the selection of the route. They could explain that our verses are presenting Hashem's reasoning not for merely the short term decision to opt for the Wilderness Route until the events of Yam Suf, but also for why the Israelites continued on it even after the Egyptian threat had already been eliminated.⁵²

"וְלֹא נָחָם אֱ-לֹהִים... כִּי קָרוֹב הוּא" – Close to where and what was the concern? These commentators assume that the verse is speaking of the route to Canaan and that the problematic issue is the shortness of the Philistine Route to Canaan.⁵³ The people needed more time to develop their connection to Hashem before their arrival in Canaan.⁵⁴

• Mekhilta DeRabbi Yishmael and Shadal explain that once they conquered the land they would disperse each to their own inheritance and no longer have the opportunity to learn Torah and be guided spiritually by Moshe.
• Netziv and Meshekh Chokhmah maintain that God feared the influence the idolatrous neighbors would have on such a fledgling nation.

Double "כִּי" and the concern of "בִּרְאֹתָם מִלְחָמָה" – According to this approach, "כִּי" mean "because" in both instances.  However, the commentators diverge in how they understand the relationship between the two phrases.

• Netziv stresses that the first reason of "כִּי קָרוֹב הוּא" was the primary one. He points out that the subsequent reason of "כִּי אָמַר אֱ-לֹהִים פֶּן... וְשָׁבוּ מִצְרָיְמָה" could have been only a secondary concern, as the people did desire to return to Egypt even on the longer path.⁵⁵  He suggests that Hashem added this second reason only because the nation would not have understood the meaning of the fear of assimilation.⁵⁶
• The Toledot Yitzchak, R. Hirsch, and Malbim, though, maintain that the reasons work in tandem. Without the benefit of a long route in which to grow spiritually, the nation would lack the trust in God needed to fight wars and win.

How does the Wilderness Route solve the problem and when?

• Experiencing miracles and dependence on Hashem – The Wilderness Route enabled the nation to witness the miracles of the Splitting of the Sea, manna, and water, all of which instilled faith in God.⁵⁷
• Receiving mitzvot – It further allowed the Children of Israel to receive the Torah and learn God's commandments.⁵⁸
• Sterile environment – The isolated environs of the wilderness protected the people from outside influences.⁵⁹
• All needs provided – The miraculous providing for their subsistence in the wilderness gave the Israelites the opportunity to grow and learn without being occupied with and overwhelmed by the normal concerns of having to work the land.⁶⁰

Parallels to the Sin of the Spies and the need for forty years – Shadal understands the forty year period of wandering in the wilderness resulting from the Sin of the Spies as similarly motivated by a need for the still immature nation to learn from Moshe and develop a stronger faith in Hashem before entering the Land.⁶¹  In both cases, the nation's unpreparedness force the postponement of the entry into the Promised Land.

"וַחֲמֻשִׁים" – This approach might suggest that choosing the longer route necessitated greater food provisions.⁶²

What about Sinai and Yam Suf? According to this approach, receiving the Torah on Mt. Sinai and witnessing miracles such as the splitting of the Sea were some of the main advantages of the route. It is unclear, though, why this is not stated explicitly in the verses.

Avoiding Philistine Route Dangers

The choice of the Wilderness Route was a response to the dangers lurking on the Philistine Route (the critical factor was to avoid traveling "דֶּרֶךְ אֶרֶץ פְּלִשְׁתִּים"). Hashem was concerned lest the wars the nation would encounter en route would frighten it into returning to Egypt.

Sources:Mekhilta DeRabbi YishmaelBeshalach VayehiAbout Mekhilta DeRabbi Yishmael,⁶³ Targum Yerushalmi (Yonatan)Shemot 13:17-18About Targum Yerushalmi (Yonatan), Shemot Rabbah #120:11-16About Shemot Rabbah, RashiShemot 13:17-18About R. Shelomo Yitzchaki, Ibn EzraShemot Long Commentary 13:17-18About R. Avraham ibn Ezra, ChizkuniShemot 13:17-18About R. Chizkiyah b. Manoach, RambanShemot 13:17-18About R. Moshe b. Nachman

"וְלֹא נָחָם אֱ-לֹהִים... כִּי קָרוֹב הוּא" – Close to where? According to most of these commentators, the verse is saying that the Philistine Route is close to Egypt, and either despite this fact, or because of this fact, it is rejected.⁶⁴

"בִּרְאֹתָם מִלְחָמָה" – Avoiding war with whom? Commentators divide regarding which enemy was on the Philistine Route which needed to be avoided:

• Philistines – Most classical and medieval commentators assume that the threat was posed by the Philistines.  According to the medieval commentators, the Philistines currently⁶⁵ living on the route itself constituted the threat.⁶⁶ However, the Mekhilta suggests that the concern was over seeing the frightening remains of previous skirmishes.⁶⁷
• Egyptians – According to modern scholars,⁶⁸ the Philistine Route might be identified with what is known in Egyptian texts as the "Wall of Horus".⁶⁹  At the time of the Exodus, it was under Egyptian control and heavily fortified with Egyptian sentries and garrisons.⁷⁰ Traveling via such a route would inevitably lead to conflict with the Egyptians, and Israelite terror of their masters would lead them to a quick surrender and return to servitude.⁷¹

Evidence and parallels – See the Akeidat Yitzchak and Abarbanel below who note that there were fearsome Philistine giants (see Yehoshua 11,⁷² Shemuel I 17, Shemuel II 21), and that these were the subject of the similar concern in Devarim 9:1-2.⁷³  The concern over the Philistine giants also parallels the Spies' trepidation in Bemidbar 13 regarding the giants in Chevron.

"וְשָׁבוּ מִצְרָיְמָה" – According to most of these commentators, Hashem's worry was that when faced with war, the nation would panic and return of the own volition to the relative safety of Egypt. Philo, though, maintains that the problem was that the enemy would actively drive the Israelites back to Egypt.⁷⁴

What about the wars with Egypt and Amalek on the Wilderness Route? While the advantage of this position is that it adopts a more literal reading of the verses, it faces a significant difficulty because despite taking the Wilderness Route, the Israelites saw battle almost immediately.  Ramban attempts to respond that the only wars that might have caused the nation to return were ones against settled peoples whose lands were being trespassed.⁷⁵  These would be protracted struggles for many years,⁷⁶ and thus posed a greater challenge in sustaining morale and preventing the nation from giving up.⁷⁷

Double "כִּי" and their relationship – These commentators agree that the second "כִּי" of the verse means "because", but they disagree about the meaning of the first "כִּי" and its relationship to the second.

• Because – Rashi and Ibn Ezra imply that it, too, means "because".  Hashem is, thus, giving two related reasons why to avert the Philistine route.  Fear of war was significant specifically because the route was so close to Egypt.  The proximity made it more likely for the nation to return to Egypt upon encountering war.
• Even though or that – R. Moshe ibn Chiquitilla‎ (cited by Ibn Ezra) maintains that the first "כִּי" means "even though",⁷⁸ while Ramban proposes that it means "that". According to both, though, the meaning is the same,⁷⁹ and the verse is giving only one reason to avoid the Philistine Route.  Even though it was the shorter (and thus seemingly more logical route), Hashem chose to dismiss it because of the danger involved.

"וַחֲמֻשִׁים" – According to Rashi the verse highlights this point because it was only due to the change of route (into the wilderness) that the nation needed to be armed with provisions. Ramban, in contrast, asserts that the verse is emphasizing how fearful the nation was of a Philistine attack, to the extent that they even armed themselves as a precaution.⁸⁰

What about Sinai? None of these commentators address the question, but one could argue that had the Philistine Route not been problematic, Hashem truly might have revealed himself somewhere on that path.⁸¹  Hashem had previously told Moshe that the nation would serve Him at Chorev, only because He is omniscient and knew in advance that the nation would ultimately take the Wilderness Route.

Combination

There were multiple reasons for the path taken.  The nation needed to avoid the dangers of war lurking on the Philistine route but there was also intrinsic value in taking the Wilderness Route.

Sources:PhiloOn the Life of Moses XXIX: 163-166About Philo, JosephusAntiquities of the Jews 2:15About Josephus, RalbagBeiur Divrei HaParashah Shemot 13:17-18Shemot 13 Toelet 1About R. Levi b. Gershom, Akeidat Yitzchak39 Question 139About R. Yitzchak Arama, AbarbanelShemot 13 Questions 1-3Shemot 13About R. Yitzchak Abarbanel

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? According to Abarbanel, Paroh believed that the nation was to return after three days.  The very fact that he was not freeing them permanently, but rather expecting them to head to the wilderness, is one of the reasons that Hashem chose the Wilderness Route.⁸²

"בִּרְאֹתָם מִלְחָמָה" – Avoiding war with whom? Both the Akeidat Yitzchak and Abarbanel maintain that the immediate concern related to war with the Philistines living on the route,⁸³ but they add that this fear would have caused the nation to cast doubts on its ability to conquer the land as a whole.⁸⁴

How does the Wilderness Route solve the problem?

• Longer route – Abarbanel points out that the war against the Philistines would have been almost immediate (due to their proximity to Egypt) and as such was much more likely to lead the nation to flee back to Egypt than later wars.
• "דֶּרֶךְ...  יַם סוּף" – In addition, only on this route was there a sea in which to drown the Egyptians.  The Akeidat Yitzchak suggests that this was the antidote to the original concern regarding war.  After the miracle, the news spread and instilled fear throughout Canaan, enabling the Israelites to more easily defeat the Canaanite nations.
• Preserve honesty – Abarbanel asserts that another motivating factor in traveling the Wilderness Route was the fact that Paroh had sent them assuming that they were leaving for a three day furlough to worship God in the wilderness.⁸⁵  If they headed towards the Philistine Route they would have been viewed as liars, and therefore Hashem led them through the wilderness.⁸⁶

Double "כִּי" – The Akeidat Yitzchak assumes that the first "כִּי" means "that" and is simply describing the route rather than explaining its rejection. The real concern was that wars encountered there would lead the nation back to Egypt.  Abarbanel, in contrast, asserts that "כִּי" in both of its occurrences means "because".  Wars on this route specifically would lead the nation to return because its proximity meant an earlier confrontation.

"וְלֹא נָחָם אֱ-לֹהִים... כִּי קָרוֹב הוּא" – Close to where? The concern related to the Philistines' proximity to the Israelites in Egypt and the fact that they would confront them a mere few days after leaving Egypt.

"וַחֲמֻשִׁים" – Abarbanel asserts that the verse is emphasizing that, even though the nation left armed and/or in military formations of fifths, they still lacked the courage to fight against the Philistines.

What about Sinai and Yam Suf? Abarbanel assumes that these were both factors in choosing the Wilderness Route.  Perhaps the route is referred as "דֶּרֶךְ הַמִּדְבָּר יַם סוּף" to hint to both events.  "יַם סוּף" refers to the miracle of the drowning in Yam Suf, while "הַמִּדְבָּר" alludes to the nation's request to worship Hashem in the wilderness.

¹ Cf. Y. Bin-NunMegadim 3, "'דרך ארץ פלשתים' מול 'דרך המדבר ים סוף'", Megadim 3 (5747): 21-32.  Like R"Y Bekhor Shor and Sforno, Bin-Nun also contends that the Wilderness Route was chosen to ensure the confrontation at Yam Suf and the drowning of the Egyptians.  However, he differs from them in his understanding of why Yam Suf was necessary – see notes below.

² See R"Y Bekhor Shor Shemot 14:2 who notes that the Israelites were obligated to return to Egypt since they had taken leave only for a holiday and also because they had borrowed the Egyptians' vessels.  And see Sforno who interprets Shemot 14:30 as the Israelites being rescued from Egyptian slavery (rather than simply from death at the hands of the pursuing Egyptian army).  Cf. the contrasting position of Josephus and Y. Bin-Nun in the note below.

³ It is even possible that the ruses of the three day journey and borrowing of vessels were designed to cause the Egyptians' pursuit and subsequent drowning.  For elaboration on these twin theories and the commentators who adopt them, see A Three Day Journey and Reparations and Despoiling Egypt.

⁴ Cf. Josephus, who suggests that the Wilderness Route was taken only "in case the Egyptians should... pursue after them".  Josephus, here (see below that he brings other explanations as well), also understands the choice of route as enabling the drowning at Yam Suf.   However, since Josephus maintains that Paroh had freed the nation for good (and that the vessels were given as gifts rather than loans), he views neither the Egyptian pursuit nor their drowning in Yam Suf as inevitable components of the Divine plan.
Y. Bin-Nun goes even one step further.  He posits that not only did Paroh free the Israelites permanently, but that had Hashem not elected to lead the Israelites on the Wilderness Route, Paroh would never have chased after them, but would have instead granted them permission to live in Israel as his vassals.  These understandings encounter some difficulty from the simple reading of "כִּי בָרַח הָעָם" in Shemot 14:5 which seems to imply that the Israelites had fled instead of returning to Egypt as planned.

⁵ In addition, see Sforno Shemot 7:4 that Yam Suf was a necessary part of the Egyptian punishment and education (see Shemot 14:5).  For elaboration, see Purpose of the Plagues.

⁶ Sforno's interpretation differs from that of other exegetes who all assume that the verse is speaking of the shortest route to Canaan.  Sforno's motivation is the need to deal with the "elephant in the room" and address the question of why the verse would even need to explain why the Israelites were not going directly to Israel.  After all, before they could have gone to Israel, their slave status first needed to be resolved, with Paroh either willingly relinquishing his ownership (highly improbable) or having it stripped from him by force (as ultimately happened at Yam Suf).
Sforno addresses this question by claiming that, in fact, the verse is not speaking about going to Israel at all, and this was not even a הוה אמינא at this stage.  See below for how R"Y Bekhor Shor and other commentators address this issue.

⁷ The geography of the region, though, makes Sforno's approach difficult, as it is hard to see how the Philistine Route could be on the way to Yam Suf.  See both Philistine Route and Yam Suf for the debate over the locations of each.

⁸ Since both routes were originating in Egypt, they were obviously equally close to Egypt. Thus, Sforno explains that the Philistine Route to Yam Suf was shorter than the Wilderness Route (according to Sforno, both led to Yam Suf), making Yam Suf closer ("קָרוֹב הוּא") to Egypt via the Philistine Route.  According to Sforno, this is also what made the route more problematic – see below.

⁹ This is the opinion of almost all other commentators as well.

¹⁰ R"Y Bekhor Shor (following Rashbam) attempts to prove that the Philistine Route was the obvious choice from Bereshit 26.  There Yitzchak is apparently considering descending to Egypt, and he first goes to the land of the Philistines.

¹¹ According to R"Y Bekhor Shor, the verses are discussing the threat posed by the Egyptian enemy, and that the point of taking the Wilderness Route was to drown the Egyptians and eliminate this threat (see below).

¹² R"Y Bekhor Shor thus disposes of the "elephant in the room" issue (see note on Sforno above) by saying that this is the very point which the verses themselves are making.  The Egyptian threat precluded entry into Israel (regardless of the route taken), and it needed to first be eliminated before they could proceed to conquer the land.

¹³ Alternatively, this position could also suggest that the coastal Philistine Route was full of Egyptian fortifications (see below that the coastal Philistines had not yet arrived), and had the Israelites taken this route, they would have been caught in between Egyptian armies.  Cf. Cassuto below who contends that, for this reason, the Coastal Route was not even a consideration (according to him, the "Philistine Route" went through the Negev).

¹⁴ Since the Israelites, despite taking the Wilderness Route, wound up seeing the pursuing Egyptian army, Sforno opts to read "בִּרְאֹתָם מִלְחָמָה" as hearing reports that the Egyptians were chasing, rather than seeing them.

¹⁵ In contrast, Y. Bin-Nun asserts that the concern was a long range one, and related to any future wars which might lead the nascent Israelite nation to return to Egypt for protection.  See above that he assumes the Egyptians were not initially planning on chasing after the Israelites, but would have willingly permitted them to emigrate to Israel and live there as Paroh's vassals.

¹⁶ According to Y. Bin-Nun, in contrast, the bondage had already been terminated with the Exodus (he assumes that Paroh permanently expelled them), and the drowning of the Egyptians at Yam Suf was intended to go a step beyond that and free the Israelites from the slave mentality of dependence on their former masters for protection.

¹⁷ R"Y Bekhor Shor is still troubled by the fact that Hashem could have taken the Israelites via the Philistine Route and simply made both the Philistines and Egyptians drop dead (thereby preventing the Israelites from panicking and also severing their bonds of slavery).  To answer this, he adds that Hashem wanted to maximize His miracles, and this was best accomplished by taking the Wilderness Route which would lead to the supernatural events of Yam Suf.  A difficulty with this approach is that this critical aspect is not explicit in the text.

¹⁸ See above that according to Sforno both routes led to Yam Suf, so this in of itself was not a factor in the selection.

¹⁹ This is in contrast to the second approach below, which focuses instead on the wilderness aspect of the chosen path.

²⁰ Cf. R. Saadia and many others below.

²¹ See above that the fact that the route was close to Egypt meant that it would be filled with informers. These informers would provide news of the pursuing Egyptian army, and this would lead the Israelites to submissively return to their masters.

²² Cf. Y. Bin-Nun who asserts that "וְשָׁבוּ מִצְרָיְמָה" is referring instead to reliance on Egypt and seeking its help in the future when endangered by other enemies.  However, his theory does not work well with other verses in the Torah in which the Children of Israel use similar language which seemingly refers to physically returning to Egypt (see Bemidbar 14:4, Devarim 28:66) or yearning for the days in which they physically resided there (see Shemot 14:11-12, 16:3, 17:3, Bemidbar 11:5,20, 20:5, 21:5).

²³ For Y. Bin-Nun, the choice of route achieved a lesser degree of success; see the note above for the many occasions (already in the Torah) on which the Israelites wanted to return to Egypt.  See Y. Barzilai, "וימרו על ים בים סוף - התכנית שלא התממשה" in על דרך האבות (Alon Shevut: 5761): 297-315, who agrees with Y. Bin-Nun's general approach, but questions why the nation continuously longs to return to Egypt if Yam Suf was designed to make them totally independent. He therefore suggests that Hashem had originally planned that the people themselves would defeat Paroh at Yam Suf. Only their own victory would give them the necessary courage to turn their backs on Egypt in the future. The nation, though, was not up to the task, and therefore Hashem wrought the miracle instead.  This saved the people, but did not accomplish the primary goal of psychologically freeing the Israelites from dependence upon Egypt.

²⁴ This is a question only for R"Y Bekhor Shor (and Y. Bin-Nun), but not for Sforno (who says that the Philistine Route did not lead to Israel at all).  R"Y Bekhor Shor could respond that the Israelites did indeed attempt to take the Philistine Route to Israel in the episode of the Spies (this would assume like Cassuto below that the Philistine Route went through the Negev).  Alternatively, once they were on the other side of Yam Suf, it is possible that the nation could no longer get back to the Philistine Route, or that it was no longer the shortest route.

²⁵ Cf. Y. Bin-Nun who cites numerous prophecies (Yeshayahu 30:2, 31:1-3, Hoshea 7-11, Yirmeyahu 2:36) which criticize the reliance on Egypt for protection.

²⁶ Malbim combines this approach with that below which speak of the nation's need for spiritual growth.

²⁷ These commentators include R. Saadia (see his commentary on Shemot 11:3), R. Hirsch (see his comments on Shemot 12:31 and 14:5), and Malbim.  R. D"Z Hoffmann appears to contradict himself on this issue.

²⁸ This list includes the Mekhilta (though not necessarily R. Eliezer himself), Shemot Rabbah, Shadal, and Cassuto.  See note above regarding R. D"Z Hoffmann.

²⁹ This is especially a problem for Shemot Rabbah which states that the purpose of the three day ruse was to cause the Egyptians to chase and drown in Yam Suf. If so, one would have expected that the text would explain that Yam Suf was part of the reason for choosing the Wilderness Route.

³⁰ In other words, the verses of Shemot 13:17-18 are a heading, not just for Shemot 13-14, but for the the duration of the stay (perhaps even the entire forty years – see note below) in the wilderness and the rest of the Torah.  While initially Hashem led the Children of Israel via the Wilderness Route in order to drown the Egyptians and remove the remaining yoke of slavery, the verses here focus on the long term benefits of the Route and explain the reason for the forty years in the wilderness.
Alternatively, since it was inevitable that Paroh would pursue the Israelites no matter which route they took, and since Hashem could have destroyed Paroh's forces on the Philistine Route as well (cf. R"Y Bekhor Shor), the Egyptian threat did not have a significant impact on His decision and is thus not mentioned.

³¹ For this approach, the critical factor is the timing, while for the third approach, the critical factor is in the geographical location.

³² See similarly R. Eliezer in Mekhilta DeRabbi Yishmael.

³³ Rambam notes that Hashem does not simply alter human nature through supernatural means.

³⁴ Rambam's position is likely influenced by the similar formulation of Ibn Ezra.  See also Ibn Ezra Shemot 2:3 who similarly explains that Hashem designed that Moshe would be raised in Paroh's palace so that he would have the psychological makeup of a free person.

³⁵ Rambam is assuming that from the beginning the nation was meant to wander in the wilderness for forty years (this is also what comes out from the Mekhilta).  A simple reading of the Torah, though, seems to imply that had they not sinned, the nation would have entered the land soon after the Revelation at Sinai.

³⁶ This is, in fact, the context of the Rambam's discussion in Moreh Nevukhim 3:32, and his explanation of our verses is somewhat of a digression intended to buttress his general position.

³⁷ See Shemot Rabbah similarly. Cf. Akeidat Yitzchak below.

³⁸ See also Mekhilta deRabbi Yishmael which is somewhat more ambiguous: "כי קרוב הוא בקרוב ירשו כנעניים את הארץ שנ' ודור רביעי ישובו הנה".

³⁹ See also similar opinions in Mekhilta DeRabbi Yishmael and Shemot Rabbah that suggest that Canaanites had ruined the agriculture of Canaan and Hashem wanted to give the land time to rejuvenate.  Another possibility raised there relates to the fact that the oath of Avraham not to harm the Philistines was still in effect, necessitating a forty year delay until conquest could begin.
All these opinions might be assuming that the nation of Israel left Egypt earlier than intended.  Had they stayed the full 430 years as originally planned, the land would have been ready for conquest, but since Hashem needed to save the Israelites from the oppression earlier, a delay was needed in the wilderness.  See Duration of the Egyptian Exile for different approaches that suggest that Hashem shortened the length of the original enslavement.

⁴⁰ Cf. the second variation of this general approach below which instead emphasizes the spiritual development and may view the conquest as a completely miraculous process.

⁴¹ Cf. Cassuto who similarly notes that Hashem's concerns were realized after the Spies report, when the nation's reaction was, in fact, precisely what Hashem had been concerned about‎ (see Bemidbar 13:22 – 14:4).  In contrast to the Mekhilta, though, Cassuto thinks that the Spies traveled via the very route that Hashem had originally eschewed in Shemot 13 for this very concern (see below that according to Cassuto, the Negev Route is identical with the Philistine Route).  For both the Mekhilta and Cassuto, though, the critical factor was the need for maturation rather than the particular route taken.

⁴² Accordingly, the decree was for constructive purposes and not purely punitive.  Cf. the approach below of HaKorem and Shadal.

⁴³ This is explicit in R. D"Z Hoffmann.

⁴⁴ The coastal route was instead filled with Egyptian garrisons who used the path on their campaigns to the North.  Cassuto suggests that as such, this route was not considered at all, leaving a choice between the shorter Philistine Route through the Negev and the more roundabout Wilderness Route.
See, below, though that some modern scholars suggest that the verse really is referring to the coastal route ("דֶּרֶךְ הַיָּם") and simply explaining that Hashem rejected it specifically due to the Egyptians stationed there.

⁴⁵ See below that Cassuto notes that this is the same path which the Spies later took and which produced exactly the results which Hashem had earlier tried to avoid.  Thus, when the Children of Israel finally (successfully) entered the land after their forty years in the wilderness, they avoided this route altogether and entered Canaan from the eastern bank of the Jordan.

⁴⁶ I.e. the "אֶרֶץ פְּלִשְׁתִּים" mentioned in Bereshit 21:32.

⁴⁷ Rashbam's position is not explicit, but is rather reconstructed from a combination of his interpretations.  In his commentary on our verse he notes that the problem with the Philistine Route was that it would bring them immediately ("מיד") to Canaan, while in his commentary on Shemot 16 he explains that the miracle of the man was intended to instill faith.

⁴⁸ Malbim combines this approach with that above, emphasizes the need for both practical preparation for conquest and spiritual growth.

⁴⁹ These commentators include R. Hirsch (see his comments on Shemot 12:31 and 14:5), Malbim, and Netziv.  See Netziv's position in A Three Day Journey for elaboration of his approach regarding the request to leave for three days.

⁵⁰ See Netziv's position in A Three Day Journey for elaboration of his approach regarding the request to leave for three days.

⁵¹ This list includes the Mekhilta (though not necessarily R. Eliezer himself), Shemot Rabbah, and Shadal.

⁵² See the previous approach for development of this approach and alternative possibilities.

⁵³ See Rashbam who notes that Bereshit 26 shows that the Philistine Route was the standard path taken between Canaan and Egypt.  [See also Rashbam Bereshit 26:1.]

⁵⁴ Netziv, in contrast, points to the negative influences of the Philistines which God wanted to avoid. The nation needed a longer, isolated route in which to strengthen their own beliefs before encountering and being swayed by the Philistines' beliefs.

⁵⁵ See, however, Mekhilta and Rashi who address this issue.

⁵⁶ Netziv is picking up on the somewhat awkward formulation "כִּי אָמַר אֱ-לֹהִים" which seems unnecessary. Thus, he understands that this reason was actually said to the nation (and is not just an explanation provided for the reader).  [Cf. R. Saadia who says that Hashem did not communicate at all with the nation on this matter, but merely caused them to naturally miss the Philistine Route.]

⁵⁷ See Rashbam Shemot 16:4 who explains that the nation's constant dependence on Hashem for its sustenance ingrained their belief in Him.  It is possible that the system of traveling only upon Divine command detailed in Bemidbar 9 was also aimed at instilling this dependence.
Rashbam understand the usages of the root "נסה" to mean "become accustomed".  [For more on Rashbam's position, see Miracles and Mitzvot at Marah.]  Cf. Philo who understands the root as to "test" and thus writes:  "He was also desirous, by leading them through a desolate and extensive country, to prove them, and see how obedient they would be when they were not surrounded by any abundance of necessaries, but were but scantily provided and nearly in actual want."

⁵⁸ See Josephus, R. Yehoshua in Mekhilta DeRabbi Yishmael, and the Keli Yekar.

⁵⁹ This is emphasized by the Netziv (this is a repeated theme in his commentary – see Netziv) and Meshekh Chokhmah.  See also the Hoil Moshe Devarim 32:11-12 who similarly explains the verse "ה' בָּדָד יַנְחֶנּוּ וְאֵין עִמּוֹ אֵל נֵכָר".  Note that when toward the end of the forty years in the wilderness the Israelites did come in contact with outsiders, they immediately committed the sin of Peor.

⁶⁰ The spiritual benefits of the "Wilderness Kollel Experience" are emphasized by the Mekhilta.  [See there Rashbi's statement:  "לא ניתנה התורה לדרוש אלא לאוכלי המן", and compare to his position in Bavli Berakhot 35b regarding the commandment of learning Torah.  Rashbi likely identified with this experience given his personal extended experience learning Torah in isolation.]  See also Shadal here and on Bemidbar 13:2 and Devarim 8:2.

⁶¹ See Shadal Bemidbar 13:2 and Devarim 8:2.  HaKorem Devarim 8:2 (cited by Shadal) also takes this position.  Cf. Rambam above.

⁶² Cf. R"Y Bekhor Shor above.

⁶³ The Midrash offers many possible reads of the verses, including some of the approaches below.

⁶⁴ However, see Chizkuni (as well as R. Chaim PaltielShemot 13:17-18About R. Chaim Paltiel and the Minchah Belulah) who suggests a more metaphoric read of the verse, proposing that the subject of "הוּא" is the Philistines themselves (not the Route) who were relatives (קרובים) of the Egyptians and thus more likely to fight against the Israelites.  Cf. Mekhilta DeRabbi Yishmael who also reads the verse metaphorically, suggesting that the phrase is referring to the oath of Avraham to Avimelekh. The oath was "too close", meaning that it was still in effect.

⁶⁵ See above, though, that it is questionable whether there were any Philistines living on the coast at the time of the Exodus.

⁶⁶ Ramban asserts that the Philistines would not want outsiders trespassing their land, and as such would fight to prevent them from doing so.  See Chizkuni and R. Chaim PaltielShemot 13:17-18About R. Chaim Paltiel below who propose that the Egyptian and Philistines were related (see Bereshit 10:13-14), making them more likely to fight the fleeing nation.

⁶⁷ According to the Midrash, thirty years earlier, members of the tribe of Ephraim had attempted to make their way to Israel, but they were massacred by the Philistines and their corpses still lay on the Philistine Route.  Hashem did not want the Israelites to see their unburied bodies, panic, and then return to Egypt.  This Midrash is found also in Targum Yerushalmi (Yonatan) and the first opinion in Shemot Rabbah, and Josephus may be alluding to an earlier form of it.  The motivation for the Midrash may be the perplexing question of why the nation would be more afraid of the Philistines than they would be from the pursuing Egyptians.

⁶⁸ See, for example, N. Sarna, Exploring Exodus (New York, 1996): 103-106.

⁶⁹ This means the wall of the ruler, and refers to the heavily guarded, defensive line protecting Northern Egypt. This might be the equivalent of the Biblical "דרך שור".

⁷⁰ See above that the coastal Philistines had not yet arrived.

⁷¹ Moreover, if Paroh decided to chase, the nation would have been trapped and feel like they had no choice but to give in.

⁷² See Yehoshua 11:22 that, as a result, the Philistine region was not conquerable at the time of Yehoshua and remained a thorn in the Israelites' side until (and even during) the period of the Monarchy.

⁷³ However, see above that these coastal Philistines arrived in Israel in only a later time period.

⁷⁴ See Chizkuni who brings a similar possibility, suggesting that the Philistines would return the fleeing slaves to Egypt. This ignores the wording of the text "פֶּן יִנָּחֵם הָעָם" which suggests that the nation themselves would have a change of heart.

⁷⁵ Amalek, on the other hand, was exceptional, as they attacked en route. As such, flight would have been pointless since the Amalekites would have continued to fight even if the nation fled.  Ramban further proposes that once the nation took a roundabout route, they no longer knew the way back to Egypt.

⁷⁶ See Shemot 23:29:  "לֹא אֲגָרְשֶׁנּוּ מִפָּנֶיךָ בְּשָׁנָה אֶחָת".

⁷⁷ Cf. Abarbanel below who suggests that the war against the Philistines would have been almost immediate (due to their proximity to Egypt) and as such was much more likely to lead the nation to flee back to Egypt.

⁷⁸ Ibn Ezra cites other examples where "כִּי" might have this meaning, but they are all debatable (see Biur).

⁷⁹ While they suggest opposite meanings for the "כִּי", they also have opposite readings of the sentence structure.  According to Ibn Chiquitilla‎, the "כִּי קָרוֹב הוּא" explains the end result of what Hashem did not do (‏"[וְלֹא נָחָם אֱ-לֹהִים דֶּרֶךְ אֶרֶץ פְּלִשְׁתִּים] [כִּי קָרוֹב הוּא]"‏), while according to Ramban it explains what Hashem did not do (‏"[וְלֹא] [נָחָם אֱ-לֹהִים דֶּרֶךְ אֶרֶץ פְּלִשְׁתִּים כִּי קָרוֹב הוּא]"‏). Their interpretations thus have the same net result.

⁸⁰ R. Chaim PaltielShemot 13:17-18About R. Chaim Paltiel raises a different possibility, that the verse is referring to the gold and silver vessels that the nation took from the Egyptians.  He suggests that Hashem feared that if the Philistines saw what the Israelites had taken, they would surely have attacked.

⁸¹ Cf. R. D"Z Hoffmann above.

⁸² See above that Netziv argues that this reason is not explicit in the verses, and as such is proof that this was not one of Hashem's motivations, for Paroh did free the nation totally and as such did not care which route they took.  See A Three Day Journey for elaboration.

⁸³ See above that Akeidat Yitzchak and Abarbanel note that the Philistines boasted fearsome giants and that these were the cause of the similar concern in Devarim 9:1-2.  However, also see above for the historical problem with this interpretation.

⁸⁴ Akeidat Yitzchak suggests that had the nation actually battled against the Philistines, it would in effect have been the first battle of conquest. Their land was within the promised borders and eventually conquered in the time of David. The fact that it took so long is evidence of the formidable challenge that such a fight would have presented to the fledgling nation.

⁸⁵ He draws on the seemingly irrelevant opening words "וַיְהִי בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" rather than the expected "ויהי בצאת ישראל ממצרים" as support that it was specifically due to Paroh's "sending them" they could not travel the other route.
In explaining the various motivations in rejecting/choosing the route, Abarbanel thus points to every phrase in the verse: Paroh's sending, the proximity of the rejected route, fear of war, and the fact that the chosen route leads to Yam Suf.

⁸⁶ Cf. R"Y Bekhor Shor above.