I agree with you, I think, about modern self-congratulation, but I am not to the section yet where Greenblatt deals with Shylock -- the whole thing is organized in terms of Shakespeare's life and periods in his life, so the plays come in more for what different imagery and metaphors might have to say about his influences and what they can tell us about his mental makeup and cultural influences, as well as where this imagery is potentially drawn from in his life. There was one mention, so far, in Greenblatt's pretty damning indictment of Shakespeare's view of marriage as inherently fucked up -- even Jessica and her suitor in The Merchant of Venice end up as highly venal figures, having ripped off this old usurer and basically become usurers, themselves, and have no likelihood of a successful union. Greenblatt argues that the only intimately observed and tightly knit marital couples in all of Shakespeare are, horribly, the Macbeths and Claudius and Gertrude. I think he's right, there. Greenblatt also supports the "second bed" bit as a telling indicator of Shakespeare's estrangement from the wife he lived almost wholly apart from.

I've skipped ahead to look at the main piece of writing about the character of Shylock, and Greenblatt seems to have a fairly liberal understanding of Shakespeare here, seeing Shylock's figure as standing far apart in individuality and roundedness from other stock figures of the Jew as usurer, especially in, apparently, a play by Marlowe called The Jew of Malta. Greenblatt discusses how Shakespeare's father and Shakespeare himself were both involved in what would have been defined as illegal usury in making loans at above 10 percent simple interest.

You should read it. It's a quick read, seriously.