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Malcontent, super-spy, social critic, avenger (no, sadly, not that kind). While Bosola's not high on our list of eligible bachelors (we're looking at you, Julia), he's definitely topping the one for interesting characters.
You may not have known what to make of this guy because it looks like he's all over the place—at one moment Bosola ruthlessly critiques the corruption of the royal court; in the next he pledges his services to the evil Ferdinand and spies on our heroine, the Duchess.
As if this isn't weird enough, at the very end of the play Bosola appears to totally change once again, claiming that he has been made to act "much 'gainst mine own good nature" (5.5.85), and avenges the Duchess and her family by murdering her older brothers.
It can look like Bosola's character just doesn't make sense, and that he's simply satisfying the plot-driven needs of Webster. But we think there's actually a lot more to Bosola, and his shifting morals and motivations are complex enough that critics have frequently suggested that this play could more fittingly be titled "The Tragedy of Bosola." Hmm. Now there's a thought.
Something very important to keep in mind when thinking about the Duchess of Malfi in general and Bosola in particular is the Renaissance social hierarchy. Remember, this play focuses on people who aren't settled into their proper social roles. The Duchess is a lone noblewoman who's trying to assert her will over that of her older brothers, and Antonio is a working man who's marrying into nobility—both big no-no's in Renaissance times.
Bosola, though, is in an even weirder situation: he's an ex-con loitering around the court, musing aloud from time to time about the perversity of the Cardinal and Ferdinand's depraved power structure. In short, he has no real place—Bosola's described as a "malcontent" and "the only court gall," but ultimately this is a guy who doesn't properly exist within the social system he's complaining about.
Bosola knows perfectly well that the Cardinal and Ferdinand are bad guys, and when Ferdinand offers to pay Bosola to spy on the Duchess, he's is absolutely against the idea (refusing, for the record, the gold Ferdinand offers him) until Ferdinand tells him that he's secured Bosola the gig of "provisor of the horse" (which, FYI, is a bigger deal than you might think—it's pretty prestigious position within the court), at which point Bosola says this:
I would have you curse yourself now, that your bounty,
Which makes men truly noble, e'er should make
Me a villain. Oh that to avoid ingratitude
For the good deed you have done me, I must do
All the ill man can invent! (1.1.273-277)
This introduces a really key concept that dogs Bosola (and everybody else) throughout the play: the client-patron relationship. If it's 1613 and you're in England (ahem, Malfi), chances are that you're on one side or the other of this social dynamic—either you're an employee, or an employer.
The Duchess and her entourage represent the client-patron relationship in its ideal form. The benevolent noble protects and provides for those who serve her; in turn her clients support her and tend to her lands. And the brothers represent its worst form—the corrupt rulers preys upon their sycophantic clients, who will do anything to please them.
In this quote in particular, Bosola's being forced into a position where he feels that he has to perform "all the ill man can invent" to pay back Ferdinand for his "good deed" of landing Bosola the provisor of the horse gig. Ferdinand is a noble in the sense that he's an aristocrat, but as a morally dishonorable person he's actually totally ignoble.
Bosola recognizes, though, that that original social nobility is going to turn Bosola himself into a terrible person, because he's now bound to do all of this terrible spying-and-murder stuff to honor the client-patron relationship that Ferdinand has initiated by doing him this provisor-of-the-horse favor.
Here's the coolest part about our man B: Bosola, more than anybody else in this play, is hyper-aware of how messed up the social system is. Given that he's constantly harshing on the court, how can he turn around and (a) knowingly join the bad guys—guys who, for the record, he openly despises—and (b) think that it's going to work out for him?
Bosola himself insists that loyal service is thankless, and when we first meet him he's coming off of seven years as a galley-slave for murders he carried out for the Cardinal, only to have the Cardinal refuse to acknowledge that not only did Bosola do what he asked, but took a major hit as a consequence. It's pretty weird, then, that for the majority of the play Bosola clearly believes that, when he's worked long enough and well enough for Ferdinand, Ferdinand is going to reward him.
But here's the thing: Bosola, more than he wants money or security, wants a place in society, and when Ferdinand offers him a title within the court, he's powerless to resist the allure of social significance. He's bound to Ferdinand and becomes his "creature" to avoid the "ingratitude" (the client scorning his patron) he mentions above. In a weird way, you could almost describe Bosola as a kind of disillusioned idealist: even though he clearly knows better, he displays a sort of inherent faith in the integrity of the bond between servant and master. He's like the kid in high school who hates on the popular kids right up until they ask him to join their clique (for free math tutoring, of course).
When Ferdinand makes it clear, after the execution of the Duchess, that he's not going to reward Bosola for his service, Bosola warns him "You are falling into ingratitude" (4.2.283), thinking that Ferdinand is working off of the same dynamic of "gratitude" that swayed him into Ferdinand's service in the first place. Bosola has figured that Ferdinand and he were using the same Honor Among Deeply Cynical Thieves Playbook, only to find out that Ferdinand, in addition to being more than a little mentally unhinged, could care less about all of this "gratitude" stuff.
As much as he wants to be a part of the courtly social structure, Bosola also clearly resents his particular job as spy-cum-assassin. This tension ties back into our original problem with this character: how can a guy who constantly talks about how much he hates the lying, cheating older brothers then go lie and cheat for them?
Again, though, you have to keep in mind Bosola's position here. He is, now, an employee, and more specifically he's an "intelligencer," which means that his spying, deception, and even acts of murder aren't the products of his personality (i.e., a guy who does bad things because he hates kittens and unicorns) so much as they're the products of his employ. To Bosola, evil isn't what he is, it's what he does. He's got orders. He gets paid—well, sort of. That's the bottom line.
As time wears on, Bosola finds it harder and harder to distinguish between himself and his job as "a very quant invisible devil in flesh: / an intelligencer" (1.1.253-54). For more discussion of this, go check out the "Lies and Deceit Theme," which features quotes and discussion about Bosola's many "shapes" and the difficulty of keeping them separate.
If Bosola's able to rationalize all of the awful things he does, though, then why at the end does he end up regretting all of it and avenging the destruction of the Duchess's family? He pulls the fastest 180 we've ever seen in drama.
Throughout the play, we see Bosola becoming increasingly aware that the Duchess is the prince he could have served. While observing the way in which the Duchess rewards the good work and integrity of her own servants, Bosola remarks, "rejoice / that some preferment in the world can yet / arise from merit […] / raised by that curious engine, your white hand." He sees that the Duchess represents, as indicated above, the way in which the courtly power structure can ideally work, but is too cynical to believe that it can last, concluding that he lives in a "miserable age, where only the reward / Of doing well is the doing of it!" (1.1.31-32).
After he has executed the Duchess per Ferdinand's command, Ferdinand refuses to pay Bosola for his services, whereupon Bosola says:
Let me know
Wherefore I should be thus neglected. Sir,
I served your tyranny, and rather strove
To satisfy yourself than all the world;
And, though I loathed the evil, yet I loved
You that did counsel it, and rather sought
To appear a true servant than an honest man (4.2.330-336)
This hearkens back to that scene in Act I where Ferdinand first offers to employ Bosola as a spy. Bosola has, at this point, done "all the evil man can invent," because he's valued his status as "a true servant" over his own moral inclinations. This speech also marks the last of Bosola's shifts in attitude, after which he decides that he has to kill Ferdinand and the Cardinal to avenge the Duchess. He finally breaks free of the client-patron relationship that's obsessed him throughout the play, and acts on all the rhetorical vitriol he's been dealing out against the corrupt brothers.
Having killed them, he says, "The last part of my life / Hath done me best service," which makes a lot of sense when you consider that this is the only part of the play where Bosola does anything in service of his "own good nature"—his inner (apparently pretty sound) moral compass.
Bosola's been playing for every team but his own: for the Cardinal, for Ferdinand, for the Duchess and Antonio, even for "Justice"—this is the first time you really see Bosola doing what Bosola wants, what Bosola thinks is right, instead of working to serve somebody else or play by anybody else's rules.
Now there's a really interesting and complicated question.
To properly address it you have to keep an obvious but important idea in mind: John Webster wrote this play. You want a happy ending? Dream on.
Bosola has, throughout the play, tested every form of advancement he can imagine—economic, social, and religious—and having been systematically disappointed in each, he finally concludes, in a famous scene, that men are "merely the stars' tennis balls" (5.4.54), tossed about without purpose or meaning.
Webster is famous for being unrelentingly bleak in his worldview (ever feel like you're getting too happy? Go read The White Devil). Even though you really want to feel like Bosola's murder of the Duchess's brothers is a moment of triumph over a degenerate society, Webster closes the play with Bosola dying of a mortal wound, saying "Oh, this gloomy world! / In what a shadow, or deep pit of darkness, / Doth womanish and fearful mankind live!" Ultimately, Bosola can't win because the problem isn't that there are these two corrupt men ruining their sister's life; the problem is that the world is a "deep pit of darkness." And how.
The society in which all the characters are trapped is inherently problematic, and Bosola's murder of the brothers is, at best, an escape from personal moral annihilation, not a true victory over the vices of the court. Ultimately, the question isn't "is Bosola a good guy," but "what can good accomplish in Webster's world?"
Not much, it would seem.