I haven't done a list in awhile, so let's have at it.
Quick note, by North American, I do in fact mean the U.S. and Canada; I just do not know enough about Mexican, Central American, and Caribbean sports to include any of those. Sorry to all my Mexican, Central American, and Caribbean readers who are eagerly awaiting to see if I included their favorite woebegone Mexican, Central American, and Caribbean cities.
5. Ypsilanti, Michigan
This is the only college town I have on the list. I don't know whose idea it was to put a comprehensive public university (or convert a teacher's college into comprehensive public university, with sports, which happened in 1956) in the same county as the University of Michigan, but how are they ever, ever, ever going to draw a steady fanbase or a winning and non-money-hemorrhaging athletics department having to compete with the Wolverines?
The only fans you will get besides alumna, university workers, and their families are contrarians like me, who's built to hate Michigan anyway as an Ohio State alum, but who also can't stand for the Eagles too hard because I'm an Akron boy. Call EMU my second-favorite MAC school.
Surprise! They don't draw fans or win. That is to say, they aren't merely unsuccessful when compared to Michigan, but are unsuccessful when compared to the rest of the MAC. In men's hoops, they have four regular season titles and four conference tournament titles (none since 1998). The women's hoops has two NCAA tourney appearances since MAC play began in '81-'82.
The football team might be the worst of the bunch. Since starting MAC play in 1976, they have one solitary football title and two bowl wins.
4. Tampa, Florida
This is also mostly here because of one team. Yes, the Buccaneers were legendarily bad for most most of their history, the Lightning had a period of awfulness combined with inscrutable owners in the '90s, and the USF Bulls are not renowned for their championships. But let's talk about the Rays.
Let's start with the obvious: pretty damn unlucky to have to play a whole season in a minor league stadium because a hurricane wiped out your normal home, but that's the Rays situation this year. But the Rays have been hit with metaphorical hurricanes for their entire existence.
The causes of the Rays' attendance woes are myriad, but the results of those woes are stark: in their 2023 Game 1 wild card game against the Rangers, the Rays drew over just over 19,000 fans, the lowest mark for a playoff game since 1919.
There were rumblings a few years ago that Tampa Bay would play half their home games in Montreal, and their problems drawing fans have been a painful issue since they've been in the league. Floridians will tell you that Tropicana Field's location is the biggest problem. It's in St. Petersburg, and kind of a hard-to-get-to-from-anywhere part of St. Pete at that.
And then, yeah, the hurricane happened. This is a shame for a part of Florida that has a deep and tremendous baseball history, from celebrated minor league teams to giving the world Dwight Gooden, Wade Boggs, Gary Sheffield, and others. It's quite impressive that the Rays are usually pretty good through it all.
3. Cleveland, Ohio
Maybe a little bit of bias comes into play here, but they're called the mistake by the lake. Their river has caught fire over a dozen times. Their baseball team has the longest championship drought in MLB. They have one single major championship since 1964. And, the Browns.
Where do you even start with the Browns? Is Deshaun Watson going to go down as the worst signing in North American professional sports history? To get a guy with dozens of sexual assault allegations against him at the time of his signing, at that?
Or maybe with the Staph infections that plagued the team from 2003-2008, leading a bunch of Browns players to sue. It's all so embarrassing, man. No wonder the rest of the country looks down on us. At least the Cavs and Guardians are good, if not champions.
2. Buffalo, New York
One can argue that there are two broad categories of fan pain: when your team gets very, very close to the ring without quite getting there, and when your team almost always sucks.
Buffalo fans get bucketloads of both. The Bills Super Bowl failures are legendary, but now they seem to be giving us the 90s all over again. How many more times is Josh Allen gonna lead the Bills to regular season greatness but come up just a little short in the playoffs?
Then of course are the Sabres. No Stanley Cups since they joined the league in 1970. No appearances in the Stanly Cup finals since 1999. No playoff appearances since 2011, which is the second longest playoff draught in major North American sports, second only to the New York Jets, who last made the playoffs in 2010.
There is a strong case to be made, though, that the Sabres' playoff draught is worse, because half of the NHL makes the playoffs (and more than half did until the Kraken joined the NHL in '21'-22), whereas only 14 of the 32 NFL teams make the playoffs each year.
I remember after the Cavs won the 2016 NBA championship, a couple of Buffalo sports fans tweeting, "Hey God! Now do Buffalo!" Now you know why.
1. Vancouver, British Columbia
I worked out my first four teams for this list in the shower, and needed to research to figure out a fifth. In researching this, I actually came to the determination that Vancouver deserves to be No. 1 on this list, just slightly, slightly edging out Buffalo.
As you might be able to glean from the rest of this list, struggling to get fan support will land you in this article, but it's secondary to failing to win. Like the Sabres, the Canucks entered the NHL in 1970. Like the Sabres, the Canucks have no Stanley Cups.
But let's talk football too, since that was a big part of the Buffalo entry. Have the BC Lions won a bunch of championships, which is a lot easier in the CFL than the NFL because there have been only eight or nine teams most of its history?
No. Since the advent of the CFL, they have only been to 10 Grey Cups, winning 6. Ottawa has also only been to 10, but while BC has played in the CFL straight since 1958, Ottawa had no team in 13 of those seasons (1997-2001 and 2006-2013).
It's interesting, because people don't talk about the Lions being bad. That's because they're usually pretty good, just not Grey Cup-worthy, and people are more focused on the Hamilton Tiger-Cats badness, who have not won a Grey Cup since 1999, and have had some truly terrible teams in that span.
What puts Vancouver over the top for me is that, unlike Buffalo, they also have an MLS that has also been unsuccessful. They have no championships and while they have made the playoffs in seven of their 14 seasons, they have won a playoff series in only two of them, and have won two playoff series in none of them. Not even making the semifinals in seven playoff appearances is pretty impressively bad.
When the Sabres have lost Stanley Cups, they haven't rioted at all to my knowledge, let alone carried out some of the most destructive riots in sports history, so Vancouver is demerited for that, as well.
Now, it is your turn. What cities have I missed, and why should they be included?
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