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 theory and text, 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 Seforno 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 both sever the Israelites' remaining bonds of servitude and display Hashem's might.

Sources:R. Yosef Bekhor ShorShemot 13:17-18Shemot 14:2-4About R. Yosef Bekhor Shor, SefornoShemot 13:17-18Shemot 14:5Shemot 14:30About R. Ovadyah Seforno¹

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? R"Y Bekhor Shor and Seforno assume that Paroh had been led to believe that the Israelites intended to return to slavery after their holiday, and was sending 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 אֱלֹהִים...‏" – Where is the destination and "קָרוֹב" to what?

• Yam Suf – Seforno contends that heading for Israel was not even a consideration prior to the drowning of the Egyptians at Yam Suf, as the Israelites needed to return to Egypt.⁶  Accordingly, the verse cannot be speaking of which path was the shortest to Israel, but rather of which was the quickest to Yam Suf.⁷   He thus posits that each of the Philistine Route and the Wilderness Route must have led to Yam Suf,⁸ but that the Philistine Route was the shorter one of the two.⁹
• Israel – R"Y Bekhor Shor assumes that the verse is speaking of which path the nation was to take to ultimately arrive in the land of Israel,¹⁰ and that the Philistine Route was the shortest option.¹¹

"בִּרְאֹתָם מִלְחָמָה" – Concern over war with whom?

• With Egypt and the Philistines – According to R"Y Bekhor Shor, Hashem's immediate concern was over 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.¹²
  
• With Egypt alone – Seforno similarly contends that the Divine concern was that the Israelites might panic upon hearing¹³ that the Egyptians were in hot pursuit and return to Egypt rather than fight.  Seforno, though, assumes that this encounter would occur even before the Israelites reached Philistine territory.¹⁴

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 so that the Egyptian masters would drown and the slavery would be terminated.¹⁵  The goal of the 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 the Israelites being exposed to a two-pronged attack.¹⁶
• Forcing a confrontation – Seforno 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.¹⁷

"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"‎).¹⁸  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,¹⁹ while the "כִּי" of "כִּי אָמַר אֱלֹהִים" explains why this option was rejected.
• Two parts of the same explanation – According to Seforno, the two phrases combine to constitute the full reason why the Philistine Route was not chosen.²⁰

"וְשָׁבוּ מִצְרָיְמָה" – R"Y Bekhor Shor and Seforno understand the phrase to refer to the fear lest the nation physically return to Egypt and its bondage.²¹

"וַחֲמֻשִׁים" – R"Y Bekhor Shor understands the verse to refer to food provisions and to be clarifying that they were well supplied enough to take the longer route through the wilderness. Seforno, 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? According to this approach, traveling via the Wilderness Route succeeding in ensuring that the Egyptians drowned at Yam Suf and that the Israelites' chains of slavery were permanently severed.²²

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

Biblical parallels – Seforno compares Hashem's plan here to the words of Devorah to Barak in Shofetim 4, "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.²³

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,²⁴ R. D"Z HoffmannShemot 13:17-18About R. David Zvi Hoffmann, U. CassutoShemot 13:17-18About Prof. Umberto Cassuto

"וְלֹא נָחָם אֱלֹהִים... כִּי קָרוֹב הוּא" – Close to where? 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.  This meant that the people would arrive almost immediately in Canaan and be forced to fight the wars of conquest before they were physically and mentally prepared for them.

Where is "דֶּרֶךְ אֶרֶץ פְּלִשְׁתִּים"? Most of these commentators do not explicitly address this issue, but most²⁵ 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,²⁶ leading Cassuto to assert that the verse instead refers to the way that leads from Egypt to Israel via the Negev,²⁷ which was home to the Philistines of Avraham's time.²⁸

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

Double "כִּי" – According to these commentators, both appearances of the word mean "because", and the two provided reasons work together, together explaining 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, when they were still not battle ready, they would inevitably choose to return to servitude in Egypt.

How does the Wilderness Route solve the problem?

• Growth through trials – Rambam emphasizes how the scarcity and hardships of wilderness life instilled courage and strength.²⁹ 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.³⁰ This generation was not encumbered by a slave mentality, and was thus more capable of dealing with the challenges of conquest and government.³¹
• Miracles as morale booster – Malbim maintains that the splitting of the sea and other miracles of the wilderness would both instill fear in the Canaanites³² and boost the belief, and hence the courage, of the Israelites enabling a victory over their enemies.
• Stalling for the Canaanites – Malbim³³ 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.³⁴

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

"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.

What about Yam Suf? This approach might suggest that the verses speak of Hashem's long range goals in choosing a route, rather than focusing on the immediate ones such as the miracle at Yam Suf. The verses could perhaps be seen as an introduction to the entire trek in the wilderness and not just as the opening to the immediately following story of Yam Suf.  Alternatively, these exegetes might suggest that Hashem had not originally planned to drown the Egyptians, and He decided to do so only after choosing this route and seeing Paroh's about-face and pursuit.

Biblical parallels – Cassuto notes that Hashem's concerns were realized only a little over a year later when the Spies traveled via the Negev Route³⁵ and reported to the nation about the giants they had encountered.  The nation's reaction was, in fact, precisely "נִתְּנָה רֹאשׁ וְנָשׁוּבָה מִצְרָיְמָה"‎.³⁶

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,³⁷ 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,³⁸ NetzivShemot 13:17-18About R. Naftali Z"Y Berlin, Meshekh ChokhmahShemot 13:17-18About R. Meir Simcha of Dvinsk

"וְלֹא נָחָם אֱלֹהִים... כִּי קָרוֹב הוּא" – Close to where? Most of the commentators who take this approach would assert that the problem with the Philistine Route was precisely its proximity to Canaan.³⁹ The people needed more time to develop their connection to Hashem before their arrival in Canaan.⁴⁰

• 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.
• Meshekh Chokhmah maintains that God feared the influence the idolatrous Canaanites would have on such a fledgling nation.

Double "כִּי" – Both occurrences of the word mean "because".

• Netziv stresses that the first reason of "כִּי קָרוֹב הוּא" was the primary one. He points out that the subsequent reason of "כִּי אָמַר אֱלֹהִים פֶּן... וְשָׁבוּ מִצְרָיְמָה" could have been only a secondary concern, as the people did desire to return to Egypt even on the longer path.⁴¹  He suggests that Hashem added this only because the nation would not have understood the real fear of assimilation.⁴²
• 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? 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.  It further allowed them to receive the Torah and learn God's commandments.⁴³  Finally the isolated atmosphere protected them from outside influences⁴⁴ and gave them the opportunity to grow and learn without the concerns of having to provide for themselves.⁴⁵

"בְּשַׁלַּח פַּרְעֹה אֶת הָעָם" – For three days or forever? Netziv suggests that by the time of the Exodus, Paroh knew that the nation was not supposed to return after three days and that he expelled the nation for good.⁴⁶  Thus, Netziv asserts that the fear of Paroh chasing was not a factor in the choice of the longer route, but only its potential for instilling faith.

"וַחֲמֻשִׁים" – This approach might suggest that choosing the longer route necessitated greater food provisions.⁴⁷

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.

Biblical parallels – Shadal understands the forty year wandering in the wilderness after 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.

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 worried that the wars the nation would encounter en route would frighten it into returning to Egypt.

Sources:Mekhilta DeRabbi YishmaelBeshalach VayehiAbout Mekhilta DeRabbi Yishmael,⁴⁸ Targum Pseudo-JonathanShemot 13:17-18About Targum Pseudo-Jonathan, 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

"בִּרְאֹתָם מִלְחָמָה" – Avoiding war with whom? Commentators divide regarding which enemy needed to be avoided:

• Philistines – Most classical and medieval commentators assume that it was the Philistines who posed the threat on the Philistine Route:

• Current threat – According to many of these commentators, the Philistines presently living on the route itself⁴⁹ constituted the threat.⁵⁰
• Previous defeat – Mekhilta DeRabbi Yishmael, Targum Pseudo-Jonathan, and the first opinion in Shemot Rabbah assert that the fear related not to the consequences of present battles, but to the remains of past wars. 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.
• Egyptians – According to modern scholars,⁵¹ the Philistine Route might be identified with what is known in Egyptian texts as the "Wall of Horus".⁵²  At the time of the Exodus, it was under Egyptian control and heavily fortified with Egyptian sentries and garrisons.⁵³ Traveling via such a route would inevitably lead to conflict with the Egyptians, and Israelite terror of their masters would lead to a quick surrender and return to servitude.⁵⁴

Double "כִּי" – These commentators agree that the second "כִּי" of the verse means "because" but disagree about the meaning of the first "כִּי".

• 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 – Chizkuni maintains that the first "כִּי" means "even though", while Ramban proposes that it means "that". According to both, 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 wars it would lead to.

"וְלֹא נָחָם אֱלֹהִים... 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.
• Chizkuni⁵⁵ 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 Egyptians⁵⁶ and thus more likely to fight against the Israelites.⁵⁷

"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 whoever fought the nation would actively drive them back to Egypt.⁵⁸

How does the Wilderness Route solve the problem? Ramban asserts that the only wars that might have caused the nation to return were ones against settled peoples whose lands were being trespassed. Amalek was exceptional, as they attacked en route. As such, flight would have been pointless since the Amalekites would have continued to fight even as the nation ran. Ramban further proposes that once the nation took a roundabout route, they no longer knew the way back to Egypt.⁵⁹

"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.⁶⁰

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.⁶¹  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.

Biblical Parallels – See Akeidat Yitzchak and Abarbanel below who note that there were fearsome Philistine giants (see Yehoshua 11,⁶² Shemuel I 17, Shemuel II 21), and that these were the subject of the similar concern in Devarim 9:1-2.⁶³  The concern over the Philistine giants would also parallel the Spies' trepidation in Bemidbar 13 regarding the giants in Chevron.

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

"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,⁶⁴ but they add that this fear would have caused the nation to cast doubts on its ability to conquer the land as a whole.⁶⁵

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.⁶⁶  If they headed towards the Philistine Route they would have been viewed as liars, and therefore Hashem led them through the wilderness.⁶⁷

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 אֱלֹהִים... 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.

"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.⁶⁸

"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 Seforno, 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 Seforno 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 Seforno 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 All commentators other than Seforno assume that the verse is explaining why Hashem did not lead the Israelites to the land of Canaan via the shortest route.  For those who assume that Paroh had granted permission to leave for only a three day journey to the wilderness, the "elephant in the room" is the question of why there is even a need to explain why the Israelites were not going directly to Israel.  After all, before they could do so, there first needed to be some resolution of their slave status, with Paroh either willingly relinquishing his ownership (highly improbable) or having it stripped from him by force (as ultimately happened at Yam Suf).
Seforno 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.  All other commentators must either assume that Paroh had expelled them permanently or provide some reason why the need to first eliminate the Egyptians goes unmentioned here.  See below for some of the various options.

⁷ In this, he differs from virtually all other exegetes.

⁸ The geography of the region, though, makes Seforno'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.

⁹ Since both routes were originating in Egypt, they were obviously equally close to Egypt. Thus, Seforno explains that the Philistine Route to Yam Suf was shorter than the Wilderness Route (according to Seforno, both led to Yam Suf), making Yam Suf closer ("קָרוֹב הוּא") to Egypt via the Philistine Route.  According to Seforno, this is also what made the route more problematic – see below.

¹⁰ This is the opinion of almost all other commentators as well.

¹¹ 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.

¹² 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 for this reason that the Coastal Route was not even a consideration (according to him, the "Philistine Route" went through the Negev).

¹³ Since the Israelites, despite taking the Wilderness Route, wound up seeing the pursuing Egyptian army, Seforno opts to read "בִּרְאֹתָם מִלְחָמָה" as hearing reports that the Egyptians were chasing, rather than seeing them.

¹⁴ 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.

¹⁵ 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.

¹⁶ 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.

¹⁷ See above that according to Seforno both routes led to Yam Suf, so this in of itself was not a factor in the selection.

¹⁸ This is in contrast to the second approach below, which focuses instead on the wilderness aspect of the chosen path.

¹⁹ Cf. R. Saadia and many others below.

²⁰ 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.

²¹ 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 lived there (see Shemot 14:11-12, 16:3, 17:3, Bemidbar 11:5,20, 20:5, 21:5).

²² For Y. Bin-Nun, the choice of route achieves a lesser degree of success.  Cf. 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 asks to return to Egypt if their dependence was severed after the miracle. 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 achieving complete mental independence from Egypt.

²³ 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.

²⁴ Malbim combines this approach with that below which speak of the nation's need for spiritual growth.

²⁵ This is explicit in R. D"Z Hoffmann.

²⁶ 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.

²⁷ 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.

²⁸ I.e. the "אֶרֶץ פְּלִשְׁתִּים" mentioned in Bereshit 21:32.

²⁹ See similarly R. Eliezer in Mekhilta DeRabbi Yishmael.

³⁰ Cf. Ibn Ezra similarly.

³¹ 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.

³² See Shemot Rabbah similarly. Cf. Akeidat Yitzchak below.

³³ See also Mekhilta deRabbi Yishmael which is somewhat more ambiguous: "כי קרוב הוא בקרוב ירשו כנעניים את הארץ שנ' ודור רביעי ישובו הנה".

³⁴ 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.

³⁵ See above that according to Cassuto, the Negev Route is the Philistine Route which Hashem eschewed in Shemot 13 for this very concern.

³⁶ See Bemidbar 13:22 – 14:4.

³⁷ 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.

³⁸ Malbim combines this approach with that above, emphasizes the need for both practical preparation for conquest and spiritual growth.

³⁹ See Rashbam who notes that Bereshit 26 shows that the Philistine Route was the standard path taken between Canaan and Egypt.

⁴⁰ 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.

⁴¹ See, however, Mekhilta and Rashi who address this issue.

⁴² Netziv is picking up on the somewhat awkward formulation "כִּי אָמַר אֱלֹהִים" 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.]

⁴³ See Josephus, R. Yehoshua in Mekhilta DeRabbi Yishmael, and the Keli Yekar.

⁴⁴ This is emphasized by the Netziv and Meshekh Chokhmah.

⁴⁵ See Shadal who develops this point.

⁴⁶ See Netziv's position in A Three Day Journey for elaboration of his approach regarding the request to leave for three days.

⁴⁷ Cf. R"Y Bekhor Shor above.

⁴⁸ The Midrash offers many possible reads of the verses, including some of the approaches below.

⁴⁹ See above, though, that it is questionable whether there were any Philistines living on the coast at the time of the Exodus.

⁵⁰ Ramban asserts that the Philistines would not want outsiders trespassing their land, and as such would fight to prevent them from doing so.  R. Chaim PaltielShemot 13:17-18About R. Chaim Paltiel, instead, proposes that the Egyptian and Philistines were related (see Bereshit 10:13-14), making them more likely to fight the fleeing nation.

⁵¹ See, for example, N. Sarna, Exploring Exodus (New York, 1996): 103-106.

⁵² 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".

⁵³ See above that the coastal Philistines had not yet arrived.

⁵⁴ Moreover, if Paroh decided to chase, the nation would have been trapped and feel like they had no choice but to give in.

⁵⁵ See also R. Chaim PaltielShemot 13:17-18About R. Chaim Paltiel.

⁵⁶ Cf. Minchah Belulah.

⁵⁷ See also 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.

⁵⁸ 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.

⁵⁹ 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.

⁶⁰ 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.

⁶¹ Cf. R. D"Z Hoffmann above.

⁶² 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.

⁶³ However, see above that these coastal Philistines arrived in Israel in only a later time period.

⁶⁴ 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.

⁶⁵ 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.

⁶⁶ 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.

⁶⁷ Cf. R"Y Bekhor Shor above.

⁶⁸ 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.