Realistic roundabout reclining
ויהי בשלח פרעה את-העם ולא-נחם אלקים דרך פלשתים כי קרוב הוא וגו’ ויסב אלקים את-העם דרך המדבר ים-סוף וגו’
And it was that Pharaoh sent the [Jewish] nation. Hashem didn’t let them travel through the land of the Philistines, for it was [too] close…Hashem circumvented the people to go through the way of the wilderness to the Sea of Reeds…
Our Sages connect the verse in this week’s parsha, which says Hashem circumvented [ויסב] the people, with a well-known practice during Seder night: “From this verse our Sages said that even a poor person in the Jewish people shouldn’t eat unless they recline [שיסב], for this is what Hashem did for them.” However, it’s hard to understand how the mitzvah of haseibah, reclining while eating matzah and drinking the four cups on Seder Night is connected in any way to the circumventing described in this verse. The latter is merely referring to traveling in a long, out of the way fashion. Some suggest that the verse is merely an allusion to the idea later created by the Sages, but perhaps there’s more going on here.
One possible explanation is based on the commentary on the Haggadah known as Ma’asei Hashem. He says that this that we say, “We were slaves to Pharaoh in Egypt” is a response to the question asked by the child: “Why is this night different in that we recline?” Reclining is a way of showing complete aristocracy, freedom, and grandeur. We respond that we recline because “we were slaves to Pharaoh in Egypt, and Hashem took us out with a mighty hand…If Hashem hadn’t taken us out of Egypt, we and our children and our children’s children would still be enslaved to Pharaoh in Egypt”. What’s the intent with this “answer”?
The intent is that if Hashem didn’t take us out with a mighty hand, how else could we have left Egypt? Another possibility is that Pharaoh willingly let us out. This wasn’t entirely unfeasible, for in the end Hashem gave grace to the Jewish people and had the Egyptians willingly “lend” their valuables to the Jews. However, if Pharaoh had willingly let us out, we would have been forever subservient to him. A slave whose master frees him will always feel a sense of debt or gratitude. This is the meaning behind “If Hashem hadn’t forcefully taken us out of Egypt”, against Pharaoh’s will, “we would still be slaves to Pharaoh.” Even with physical freedom, we would have felt an eternal debt to Pharaoh. The slave mentality wouldn’t be so easily shaken off.
Reclining shows a sense of exaltedness, bordering on arrogance. It’s rather strange that we spend so much time acting this way during the Pesach Seder. The children are obviously wondering what’s going on. The response then is that it’s to show that we truly, in every way, are free. It’s not that we are denying the good that Pharaoh did for us by freeing us. Since it was against his will, there’s no gratitude to feel! As such, there’s no feeling of subservience towards Pharaoh at all.
Now, even if we take for granted that Pharaoh and the Egyptians freed us against their will, there’s a problem. At the end of the day, what sealed the deal was that we got permission from Pharaoh to leave Egypt. It was his final say which did it. Some say that Pharaoh even escorted the Jews out of Egypt. As already stated, the Egyptians even willingly gave their precious items to the Jews. It was done with a spirit of enthusiastic intent. If so, there’s still a danger that the Jews would feel some sort of gratitude towards Pharaoh and the Egyptians. That would diminish the freedom of the Jewish people, making them somewhat subservient to Pharaoh, even to this day.
Therefore, Hashem circumvented the Jews to go through the path of the wilderness. This sparked a chain of events where the Egyptians felt they could overtake the Jews and reacquire them as slaves, or worse, annihilate them entirely. If it weren’t for Hashem’s great miracle that was to follow, namely the splitting of the Reed Sea, who knows what would have happened to the Jews. As such, any glimmer of appreciation for Pharaoh that could have manifested was instantly removed.
The connection between the ויסב of this week’s parsha and the שיסב of Seder Night is now clear. Only through Hashem circumventing the Jews was there a complete and total freedom from slavery. The Egyptians chased after the Jews, removing any possibility for appreciation to them for freedom. The only road to salvation was from Hashem Himself. Once there’s complete and total freedom from slavery, this needs to be physically demonstrated Seder Night, where we’re showing and expressing our gratitude for Hashem freeing us from Egypt. Only because Hashem took us on a roundabout path are we able to genuinely recline Seder Night.
 Based on Be’er Yosef to Exodus 13:18
 Exodus 13:17,18
 Shemos Rabbah 20:18
 Pesachim 10:1
 Written by Rav Eliezer Ashkenazi, the author of Yosef Lekach on Megillas Esther. The Chida writes in Shem HaGedolim that he was head of the Bes Din in Krakow after the Rema. He was gifted in all areas of wisdom and was unique in his generation. Everyone would send him their halachic inquiries
 See further in the Be’er Yosef, where he uses this approach to explain a puzzling gemarra (Pesachim 116a), which uses a metaphor of a slave’s gratitude towards his master for freeing him with silver and gold. Seemingly, this refers to Pharaoh sending the Jews free with the Egyptians’ precious items. However, the Be’er Yosef reinterprets this gemarra, using the above approach, as referring to a slave’s gratitude towards his Master, namely Hashem, for freeing him with great wealth