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The "pound of flesh" bargain is the result of Shylock and Antonio's dueling plans
Shylock wants to either kill Antonio or run him out of Venice so that he can conduct business without Antonio's interference; he loses nothing by having the debt repaid. Antonio is already in debt (other creditors are mentioned in 3.1), and therefore will not be able to pay the debt even if his ships succeed. He's depressed and thinks that the best solution is to take the deal and hopefully die in Bassanio's arms. Then Jessica elopes, Bassanio gets married and everything goes pear-shaped; Shylock winds up motivated by revenge, not economics, and Portia feels compelled to come to the rescue.

Portia was trying to help Bassanio cheat.
Listen to the song that she arranges to have play to "help him think" while he's trying to pick a casket:
Tell me where is fancy bred
Or in the heart, or in the head
How begat, how nourish-ed
Totally wouldn't put it past her.
  • There's actually been a lot of scholarly debate on this one.

Old Gobbo had an affair with Shylock's wife, Leah, and therefore may be the father of Jessica.
Launcelot does hint that his father was a cheater, and Jessica is described as not looking or acting anything like Shylock. Years ago, Old Gobbo (then Young Gobbo) worked for young Shylock and his young, pretty wife. The reason Launcelot has a job with Shylock is that Shylock had to hire him because of past history—his former servant came knocking on his door and begged him to take in his son.

Launcelot either knows Jessica to be his half-sister or merely suspects. Either way, his jokes about Shylock not really being her father have a level of truth, and are meant to open her eyes to the possibility.

Shylock also suspects this, but he's in denial. This explains a lot of his actions—his furious insistence that "my daughter is my flesh and my blood", and his pain at the loss of the ring. (He'd be upset either way, of course, but think of it like this...he suspected all along that his wife, who he loved, never really loved him, and now it turns out that his daughter, who might not even be his daughter, doesn't love him either.)

  • There are similarities between "Merchant of Venice" and Marlowe's play "The Jew of Malta". One such similarity takes the concept of "daughter by another man" speculation a bit further, by having Barabas (the titular "Jew of Malta") poisoning an entire convent, in which his daughter now resides. Of course, this would imply that Barabas was revenging himself and not merely evil, which goes against Marlowe's concept of Barabas as a mustache-twirling one-dimensional melodrama villain.

Launcelot only worked for Shylock on the Jewish Sabbath.
In sixteenth century Venice, Jews were forbidden by law from having Christian servants. The legal exception was the Sabbath Day, when the Jews couldn't work themselves (day of rest, and all that) and had no choice but to hire Christians to do their work for them, even down to little things like lighting the fires.

This helps to explain why Shylock is so eager to get rid of Launcelot. All stereotypes aside, who would want to feed, clothe and shelter someone who only worked one day a week?

Antonio planned the bond so that he could forcibly convert Shylock and humiliate him
Why else would Antonio have provoked him before he made the loan. He most likely kept making fun of Shylock so that he would have a reason to get revenge on him. Portia and the others, including the duke helped him with this plan. Lorenzo also loved Jessica, and so they decided that it would be a win/win to steal her away, for Shylock would be sad and want revenge, and Lorenzo would get to marry the love of his life and convert her to Christianity. Then, when Shylock tried to get revenge, Portia deliberately made him fail, thus breaking him and forcibly converting him too. That means that he never had a chance the whole time, and it also means that Antonio wasn't even scared of him. It also means that they wanted to humiliate him so much, they decided to give him false hope.

Shylock commits suicide shortly after the events of the play

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