It's the most trivial of offenses in light of the rest of his rap sheet, but the fact remains that Christopher Columbus led directly to the worst ever episode of The Sopranos. (Warning: the following contains extensive Sopranos spoilers, but really, it's been seven years since it ended. It's fine.)
The plot of the episode — titled "Christopher" and written by Michael Imperioli, the actor who played Christopher Moltisanti on the show — is silly on just about every dimension. It's Columbus Day. There's going to be a parade. A Native American group is planning to protest the parade, because genocide. And for no apparent reason at all, Silvio Dante — who has previously demonstrated no interest in politics or history or really anything other than the operations of the Bada Bing — decides to devote substantial DiMeo crime family manpower to preventing the protest.
It'd be one thing if the group happened upon the topic organically — if, say, Meadow Soprano had picked a fight with her father on the topic, and then he decided to make a big deal out of it. That'd make a modicum of sense. Meadow loves nothing more than showcasing her sophistication in front of her parents (see her fight with Carmela over whether there are gay themes in Billy Budd). But no. Silvio happens upon the issue because Bobby Bacala read about it in the newspaper. It's the flimsiest possible foundation to ground an episode upon.
The whole opening scene (which, like the rest of the videos linked here, is sadly not embeddable but can be seen here) amounts to a clunky attempt to cram background on the Columbus controversy into dialogue. "It's these Indians and the commie fucks," Ralphie Cifaretto, a sociopath with no previously demonstrated interest in current affairs, offers. "They want to paint Columbus as a slave trader instead of an explorer." It sounds like a more profane version of the "Controversies" subsection on Columbus's Wikipedia page, as dictated for an audiobook. It'd be one thing if the script played it for laughs, as an example of the team's willingness to opine at length on topics about which they're ignorant. But it doesn't. It's played completely straight. Silvio's position is even treated a little sympathetically.
The show couldn't really explain why without breaking the fourth wall, but The Sopranos provoked a bit of a backlash among Italian-American groups for perpetuating Cosa Nostra-related stereotypes of Italians as a whole. The episode at times reads like an attempt by the writers to thumb their noses at the critics, but at others it appears to be apologizing to them by showing that yes, the Mafia is a tiny fraction of the overall Italian-American community. All the mob wives go to a talk by a professor specializing in issues of Italian-American identity, hitting on these exact notes. "For those who say Italian Americans eat smelly cheese and sip cold wine," she declares, referencing a stereotype I'm pretty sure isn't an actual thing, "tell them we're from the land of aromatic Asiago and supple Barolo." Sure?
Similarly, what Native Americans are portrayed in the episode are shown to be either fanatics (the protestors), or else corrupt and willing to sell out their heritage for cash (the chief to whom Tony reaches out in an attempt to stop the protest). Even though David Chase and the staff clearly agree that Columbus Day is unseemly, they for whatever reason decide to put that case in the mouths of wholly unsympathetic characters. "Mussolini was Hitler's bitch!" one protestor yells, as if that has anything to do with anything.
The Soprano who turns on Columbus isn't Meadow, but AJ (AJ?), who's depicted unthinkingly regurgitating Howard Zinn's A People's History of the United States. "It's the truth, it's in my history book!" he declares, because he's AJ, and AJ is very dumb. Ultimately, the episode seems to come down on Tony's side: Yes, Columbus was a hero, but Silvio's focus on Italian heritage is myopic, and at some point you have to move on.
But the worst part isn't even that the politics of the episode are inconsistent and often wrongheaded. It's that the dialogue sounds like it was written by an eighth-grader assigned by his history teacher to write up Columbus's pros and cons. It's basic to the point of insulting, lacks any of the wit or verisimilitude of the show's writing at its best, and doesn't reflect anything about the characters assigned to speak it. It's hard to believe it comes in the same season as "Whitecaps," which featured perhaps the best-written marital fight in the history of television.
The other plots in the episode mostly amount to place-setting for the rest of the fourth season, and are rushed through to make room for sophomoric exchanges about Columbus. Ralphie dumps Rosalie Aprile, and is dumped by Janice Soprano in turn. Bobby's wife dies, setting up his marriage to Janice, a huge part of later seasons. Pie-O-My, Ralphie's horse who Tony came to love more than any human living or dead, is introduced for the first time. Johnnie Sack learns that Ralphie mocked Sack's wife for her weight, prompting a significant rift between the New York and New Jersey crime families. These are all interesting, important plot developments that easily could have consumed the whole episode — and should have. But for some reason they got mashed up with a middle school term paper about Italian-American identity instead.
My colleague Todd VanDerWerff wrote up a much more comprehensive takedown of the episode at the AV Club, which really drives home what a perverse accomplishment it is: "It’s not just the worst episode. It’s the worst episode by SEVERAL DEGREES. The show had not been this bad before, and it would not get this bad again." Thanks, Christopher Columbus.
If you're a Sopranos fan, be sure you read Martha Nochimson's great piece on how David Chase ended the show.