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Antonio is a rich Venetian merchant, Bassanio's BFF, Shylock's archenemy, and the guy who puts up a pound of flesh as collateral so Bassanio can borrow money in order to woo Portia in style.
While Hamlet may be Shakespeare's mopiest character, Antonio sure gives him a run for his money. When the play opens on the streets of Venice, Antonio appears onstage and tells his buddies that he's totally bummed out but doesn't know why: "In sooth, I know not why I am so sad. / It wearies me, you say it wearies you" (1.1.1-2).
So why's this guy so emo? Solanio suggests that Antonio's "mind is tossing on the ocean" because all his money is tied up in various mercantile ventures (1.1.8). But Antonio gives a pretty detailed explanation of why that's not true and declares, "my merchandise makes me not sad" (1.1.46). When Solanio says, "Why then, you are in love" (1.1.47), Antonio's response seems half-hearted. "Fie, fie!" (1.1.48), he says, which isn't exactly convincing. So is it possible that Antonio is lovesick?
His depression certainly suggests that he is. In the 16th century, people thought love really could make a person sick, or "melancholy." This, by the way, is why in Hamlet, Polonius thinks Hamlet is acting like a madman. Ophelia's dad is convinced that everyone's favorite Danish prince is "mad for [Ophelia's] love" (1.2.95).
If Antonio is in love, who's the object of his affection? For a lot of audiences and literary critics (like W.H. Auden) the answer seems to be his BFF, Bassanio. As soon as Antonio has a chance to speak to his friend privately, the first thing on his mind is the woman Bassanio is wooing. It becomes clear that Antonio has asked about it before and has been promised an answer this day. One might clearly draw a link between Antonio's sadness and the weight of Bassanio's impending courtship—Antonio is suffering because he is about to lose his friend.
The question in the subtext is whether the feelings Antonio has for Bassanio go well beyond the bounds of friendship and cross over into the territory of romantic love. This might explain Antonio's sadness, his willingness to do anything for Bassanio, and most important, his constant need to contrast his friendship with Bassanio to the latter's relationship with Portia. He calls Bassanio away from what should be his wedding night to see him in Venice, and as he prepares to die in court, he tells Bassanio to have Portia be the judge of these proceedings. She will have to decide whether "Bassanio had not once a love." (That is, if he had ever had a love before.)
Antonio cannot love Bassanio the way he wants to; he can give him neither marriage nor money (as Portia can). If he were to sacrifice his life for Bassanio, he would be doing something greater than Portia ever would or could. His offer of a pound of flesh is a symbolic chance for his flesh to be meaningful to Bassanio. Even after Antonio is off the hook, he pressures Bassanio to give away Portia's ring, claiming that his own love for Bassanio and what Balthazar deserves should be more important than Portia's commandment.
This tension is weakly resolved at the end of the play when it is revealed that Portia has given Antonio his life back twice—once in court disguised as Balthazar and once more with the news of the successful ships. Portia has warmly welcomed Antonio, but her actions have managed to assert that her love for Bassanio and her power (shown by what she can give) supersede Antonio's friendship with him.
Not everyone reads Antonio this way. In an interview with NPR, actor Jeremy Irons said he sees Antonio as a melancholy "father-figure" to Bassanio. "He rather loves the boy like a son," says Irons, who even goes so far as to invent a back-story for the character that's not original to Shakespeare's play.
When Irons played the role in the 2004 film adaptation, he imagined that Antonio had once been married and, after losing his wife during childbirth, he decided to surround himself with young friends like Bassanio. Hmm. We certainly have some ideas about this back-story, but what do you make of it? You can listen to the entire interview here.
Antonio sure seems like the most devoted BFF ever, but, as you've probably noticed, he's also kind of a martyr. When he's hauled off to jail and it's looking like Shylock is going to get his pound of flesh, Antonio writes a letter to Bassanio, asking his friend to return to Venice:
"Sweet Bassanio, my ships have all miscarried, my
creditors grow cruel, my estate is very low, my bond to
the Jew is forfeit, and since in paying it, it is impossible
I should live, all debts are cleared between you and I if
I might but see you at my death. Notwithstanding, use
your pleasure. If your love do not persuade you to
come, let not my letter." (3.2.28-334)
Hmm. Is it just us, or is Antonio trying to guilt-trip Bassanio into leaving Belmont (and Portia!) in order to prove his "love" for his self-sacrificing friend? Sure, we can understand why Antonio wants his pal by his side as he faces almost certain death at the hands of Shylock, but Antonio lays it on a little thick here. Later, at the trial, Antonio says dramatically: "Give me your hand, Bassanio; fare you well. / Grieve not that I am fall'n to this for you" (4.1.277-278). It seems like Antonio is enjoying wallowing in the fact that his life is about to be sacrificed for his friend's sake.
Antonio is clearly very generous, and he most definitely loves his friend Bassanio, but he's got an ugly side as well. A blatant anti-Semite, Antonio is hostile toward Shylock and is always running around the Rialto talking trash about Jews and their practice of usury (charging interest on loans, especially overly-high interest). (Did we mention that Antonio gives out interest-free loans to his Christian friends in order to undermine Shylock's money-lending business?) At one point, Shylock complains:
[…] he hates our sacred nation, and he rails,
Even there where merchants most do congregate,
On me, my bargains, and my well-won thrift,
Which he calls "interest." […] (1.3.48-51)
When Antonio is confronted about his aggressive behavior, he's completely unapologetic. Even after Shylock reminds Antonio that he's called him a "misbeliever, cutthroat dog" and has spat upon his coat (1.3.121), Antonio doesn't deny it: "I am like to call thee so again," he says. "To spet upon thee again, to spurn thee, too" (1.3.141).
Antonio's not the only one who taunts Shylock, but he sure seems like the worst offender, don't you think? So does Antonio's abuse at least partially explain Shylock's villainy? Shylock thinks so, especially when he declares: "the villainy you teach me I will execute" (3.1.70-71).