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The White Sox beat their win total. Where do they rank among disappointing Chicago teams?

The Chicago White Sox began the season with historically low win total odds, and despite still possessing the second-worst record in baseball, they hit the over this week.

Ricobene’s for everyone!

The total opened at an unbelievable 49.5 wins and crept up to 54.5. The White Sox were sufficiently competent not-terrible that they covered even the high end of that with weeks to spare. The South Siders entered Saturday with a whopping 57 wins. They’re only five away from eclipsing their 2023 win total.

No one is throwing a parade for a last-place team, but the bar was set so low that an ordinary bad season, instead of a historically bad one, is a form of success. The Cubs are going to the playoffs, but next to them, the White Sox’s second-half surge might be the second-best sports story in town … if Caleb Williams and the Bears don’t get it together this season.

Chicago-based columnist Jon Greenberg and sports betting editor Dan Santaromita discussed their reaction to the original win total as well as what this means for the team going forward.

Santaromita: I know the White Sox were a complete dumpster fire last year, but I still couldn’t believe the win total was so low when the odds first came out. I jumped on it (admittedly a bit late at 53.5 wins), not out of a sense of fandom, but as a general rule of betting. It’s like betting an under on a college football game with a total in the 70s. Hours later, a Cleveland Guardians fan texted me about it as a form of trash talk, so I double-dipped and we bet dinner on it. If you can avoid giving juice on a bet, do it.

The White Sox were on pace to be right around the number for much of the season, with the total even dropping to 52.5 at the All-Star break, but they got better as the season went on. The thing about not having any good veteran players is you don’t have any good veteran players to trade away at the deadline, which would make the team worse for the end of the year.

Jon, did you ride the White Sox win total roller coaster?

Greenberg: Indeed I did, with this very story in mind. When I was in Arizona for spring break, I planned on going to the DraftKings sportsbook near my in-laws’ place to place a bet on the over so I could write about it. I wound up just doing it online, and because of mixed success betting the NCAA tournament, not for very much money. I got it at 53.5 right before the season started.

I know some of the “Section 108” guys bet it at 49.5, and I said they should’ve thrown a 50-win party in the tailgating lots, but they didn’t listen.

In my season predictions, I had the Sox going 56-106, but they’ve already blown through that guess too. The Sox youth movement is showing some positive signs. Maybe the 2026 win total will be something more respectable, like 59.5 wins.

Right now it’s kind of a success story on the South Side, compared to the dismal last three seasons. Here’s my short list for the best vibes in town (sorry, I don’t count the soccer or college teams):

  1. Cubs: And the vibes aren’t even that great, considering their lackluster trade deadline and the regressions by Kyle Tucker and Pete Crow-Armstrong.
  2. White Sox: They entered Friday .500 since the All-Star break, a cherry-picked kind of stat that is made for RSNs and team media, but it’s still true. The good news is it’s the prospects who are carrying the load, led by Kyle Teel and Colson Montgomery, the latter being one of the best stories in Chicago.
  3. Bears: All it will take is a couple of wins (literally) to put them at No. 1. Heck, just some good games from Williams. Vibes are low after the Week 1 loss to the Vikings, but there’s a long season ahead.
  4. Blackhawks: Connor Bedard and the gang are about to start training camp, but the Hawks are only being followed by the diehards right now. They need to start winning to get casual fans to tune in.
  5. Bulls: The Bulls are another team that can make a big jump with some competitiveness. Chicago fans want to believe in this organization, and Matas Buzelis has star potential. But did you know they haven’t been over .500 past the first week of November since 2021? Hard to get excited about a sub-. 500 play-in tournament team.
  6. Sky: Yikes. I don’t blame Angel Reese for speaking out, even if she was a little clumsy with some of the delivery. Frankly, she should be trying to force a trade. A big-name player trying to skip town is basically the only tradition the team has.

What’s your list?

Santaromita: As someone who worked at an RSN, you are spot on about the White Sox in the second half. I’m not going to say I am optimistic about the Sox going forward, but I do think the worst is behind them. I still don’t have them second in my vibe rankings, though.

  1. Cubs: The Brewers created some separation in the NL Central, so this feels more like winning by default, but they’re still a solid playoff team.
  2. Bears: I’m not sure where we are with the Bears’ cycle of hope, but that Monday night loss was like so many before. I still believe Williams can be good, and I think Ben Johnson was a good hire, so there is at least more reason for hope than the rest.
  3. White Sox: The kids apparently can play, but I don’t have a lot of faith in ownership spending the money to compete. If they do, the No. 2 slot is possible, but I don’t expect this team to contend for a playoff spot in 2026 without reinforcements.
  4. Bulls: Hey, look, the Bulls are in the middle. Even in my rankings, they aren’t bad enough to be at the bottom, but not good enough to warrant excitement. The Bulls will win more than the White Sox for the next year (maybe two), but if we’re talking vibes, Bulls fans are probably more unhappy right now than Sox fans.
  5. Blackhawks: Wasn’t Bedard supposed to be better than this? Maybe he doesn’t have enough help. The Blackhawks are the White Sox with less excitement about the young players.
  6. Sky: The Sky actually finished dead last (tied with Dallas at 10-34) in the WNBA. It’s not a pretty picture.

As a soccer fan, I will say that if we included the soccer teams, the Red Stars would be last. They have two wins in 19 matches!

To bring it back to the White Sox, do you think they will spend any money anytime soon, or should Sox fans just be counting the days until Justin Ishbia takes over?

Greenberg: I wouldn’t expect them to spend anything more than filling out a major-league roster. They started 2025 with a major hole in their budget because of their RSN fiasco, and the Ishbia announcement noted he was pumping money into the team to pay down debts. Comcast and CHSN didn’t resolve their stalemate until early June, and I have to imagine the finances there are still pretty dire. Attendance-wise, they are at the bottom of baseball, ahead of just the Marlins and the two teams playing in minor-league parks. According to Spotrac, their $77.2 million payroll is actually behind the Athletics and ahead of only the Marlins. I don’t expect it to go up by much.

If they had a sense of humor, they would join with their sports-betting partner and have a “Win Total Over” banner-raising party.

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