Caption Contest Commentary

In my fellow Chicagoan Pat Byrnes’ drawing, two mobsters have fitted their latest victim with concrete shoes and thrown him off a pier and into the river. His head, however, remains above water because he’s landed safely on top of a pile of other victims. He’s saying something to the mobsters on the pier. My…
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In J.B. Handlesman’s cartoon, a bartender is addressing Ulysses S. Grant, whose face appears on a huge $50 bill. Ron Chernow, who wrote the Alexander Hamilton biography that Lin-Manuel Miranda turned into a smash Broadway musical, recently wrote a biography of Ulysses Grant, so I initially imagined the bartender speculating about Grant’s chances of becoming…
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Charles Barsotti has drawn a robber on a therapist’s couch. Next to him is a huge bag of stolen money, and the therapist is sitting in a chair. The robber/patient is talking happily. There’s always a temptation when captioning a Barsotti cartoon to reference his classic drawing of a piece of pasta saying into the…
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In Kim Warp’s drawing, a cowboy on a horse is consulting a book and addressing a fallen cowboy he’s lassoed around the ankles. I first thought about the trope—common in old westerns—of dragging a cowboy behind a horse. In Warp’s drawing, of course, the lassoed cowboy is in front of the horse. Maybe, then, the…
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