Character Analysis
Best in the Biz?
In the words of Luther Coleman, "There ain't a better inside man alive" than Henry Gondorff.
But by the time Johnny Hooker goes to meet Gondorff, all he finds is a drunk who lives in a spare room next to a creepy carousel, looks worn out by life, and is tired of the conning game. It's, um, less than impressive.
When asked what happened to him, Gondorff explains that he tried to con a United States senator:
HENRY GONDORFF: A real lop-ear. He thought he was gonna take over General Electric. Some Chantoozie woke him up, though, and he put the Feds on me.
In Hooker's mind though, this is just a nice way for Gondorff to say that he blew it. Which: fair enough.
After he was fingered by the police, Gondorff explains that he "lammed it around for a while while things cooled off. Philly, Denver, Baltimore, nuthin' towns." But at the end of the day, his career as a conman had taken a huge hit and he eventually retreated to Chicago to put his life back together. Ouch.
Unsurprisingly, given that past, Henry isn't initially interested in running a big con. But the longer Hooker talks to him, the more we realize that Gondorff is a conman for life…and will never be able to let go. We know that he's addicted to the thrill of the criminal life, because, as he says to Hooker:
HENRY GONDORFF: No sense in being a grifter if it's the same as being a citizen.
True enough, Henry Gondorff. True enough.
The Brotherhood Mentality
Of all the things that make Henry a great conman, one of the most important is the trust he puts in the people who work big jobs with him. Unlike Johnny, Henry's willing to totally put his fate in the hands of other conmen and to rely on the sense of community that exists between these men.
That's why he's so frustrated when he finds out that Johnny has been keeping dangerous secrets from the rest of his men. Henry shows this frustrations by reminding Johnny that he needs to trust other conmen if he ever wants to run a major operation, saying,
HENRY GONDORFF: You can't play your friends like marks, Hooker.
It's at this point that we realize Johnny will have to learn to be more like Henry if he's ever going to be a truly great conman.
We know that Henry is a seasoned pro by the way he constantly uses the special lingo of conmen all over the northeast. For example, he wastes no time in sizing Doyle Lonnegan up and telling his conmen buddies,
HENRY GONDORFF: We'll use the wire. Never known a gambler who wouldn't like to beat the ponies.
In this case, the wire refers to a special kind of con where the men set up a fake betting bar. On top of that, Henry constantly uses terms like "the shut-out" and "chantoozie" to help establish that he's lived in the conning world most of his life and knows the vocab inside and out.
Under Your Skin
One of Henry's greatest gifts as an inside man is his ability…to be super irritating. (Ooh: being an inside man seems like a super-fun career choice.)
He gets in Doyle Lonnegan's head right away by knowing just how to needle the guy. When he sits down and starts beating the guy at cards, he says:
HENRY GONDORFF-AS-SHAW: Tough luck, Lonnihan, but that's what you get for playin' with your head up your ass. Couple more like that and we can all go to bed early, huh boys?
This might seem like boilerplate annoyingness, but it's actually full of jabs specially tailored for Lonnegan: by mispronouncing his name, Henry is suggesting that people might not know who Lonnegan is (and Lonnegan thrives on fame) and by including the chummy phrase "huh, boys?" Henry is aligning himself with the other players and undermining Lonnegan's authority.
The end result? Lonnegan isn't able to make good decisions because he's too busy feeling rage at Henry. And Henry only gets him more riled up when he calls him out for welching on his bet, saying,
HENRY GONDORFF-AS-SHAW: What! Don't give me that crap you little weenie. How do I know you ain't gonna take a powder?
Henry Gondorff isn't the kind of character who changes a whole lot over the course of the story…but then again, he doesn't need to. The strengths that led Luther to call Henry the "best in the biz" are just as apparent at the beginning of the movie as in the end. All Henry needed to get back to playing his A-game was an incentive to stop boozing and start getting his con on.
Henry Gondorff's Timeline