The 2024 Chicago White Sox have a chance to be the worst team in MLB history

Photo by Nuccio DiNuzzo/Getty Images

It was just plain ol’ awful for the White Sox not that long ago. Now they have the chance to make some truly miserable history down the stretch.

Well, folks! After a trade deadline that had more fireworks before the actual deadline than on the actual day and in this awkward period where nearly every team is adjusting to having newcomers on their squad, I regret to inform y’all that it’s time to talk about the Chicago White Sox once again. I did this earlier this season when they were in the midst of what was a franchise-record 14-game losing streak. Now, here we are a couple of months later and not only have the 2024 White Sox broken that record that had been set by the 2024 White Sox, they now have a pretty good shot at smashing that record to bits and joining the ranks of some of the most truly awful baseball teams of all time.

Yep. For a situation that seemed to be impossibly bleak not even all that long ago, things have somehow gotten even darker for the Pale Hose. They’ve now lost 17 straight games, with the 15th-straight loss in particular was yet another painful moment where they served as the background characters in what could be Bobby Witt Jr.’s MVP highlight reel.

After getting a merciful day off today, they’ll have to go north and face the Minnesota Twins. I’ll start this off by saying that it’s always very precarious to predict a sweep in any given Major League Baseball series and in Minnesota’s case, they’re in a tiny bit of a rough patch at the moment after they lost a series in New York against the Mets and then had what was described in a headline from The Athletic as a “disheartening” trade deadline. With that being said, Minnesota’s still right in the middle of the Postseason conversation and the Twins have gone 9-1 against the White Sox this season — including a four-game sweep at Target Field back in April.

Also, if the Twins had a “disheartening” trade deadline then what the White Sox did was just flat-out depressing. While Chicago did manage to hold on to both Garrett Crochet and Luis Robert Jr. (at least until the winter, most likely), they sent out Paul DeJong, Tommy Pham, Erick Fedde and Tanner Banks at the deadline. They even managed to get Baltimore to take on Eloy Jiménez (which was cause for actual celebration for their official RSN!), so this wasn’t a complete disaster of a deadline for the White Sox. With that being said, here’s how Andrew Mearns described how the deadline went for the South Siders:

It’s an awful time to be a White Sox fan. They’re the worst team in baseball by a mile, they’ve broken their franchise record for longest losing streak twice this year alone (their current 16-gamer is the new low), and even after all that, they won’t even pick higher than 10th in next year’s draft. So it’s just another poke in the eye that their sales at the Trade Deadline were uninspiring. Congrats to 88-year-old owner Jerry Reinsdorf on dumping the Eloy contract though, I’m sure that he really, really needed the money and will totally reinvest it.

Oof! That’s honestly the best and rosiest way to describe how the 2024 trade deadline went for the White Sox (and a lot of other teams, if we’re being completely honest). As far as Baseball America’s prospect rankings are concerned, not a single Top 100 prospect was traded at the deadline — which is to say that Chicago fans probably won’t be looking at a future so bright that they’ll need to wear shades. With that being said, we are talking about a 27-win team that is led by Luis Robert Jr. with a grand total of 1.1 FanGraphs WAR on the season. Garrett Crochet is a star-caliber pitcher as evidenced by his 4.1 fWAR on the season but both the second-and-third placed pitchers on the White Sox’s pitching fWAR leaderboard are all out of town now which means that the second-best pitcher on this team is now Chris Flexen. I’m saying all of that to say that the White Sox probably shouldn’t have expected any deals that would’ve rocked their organization to the core.

Instead, they’ve gotten worse in the short-term for what may be negligible long-term gain. Once again, “depressing” is the word that comes to mind. This also means that history may be beckoning for this team here in the dog days of summer and heading into the home stretch of the season in September. Should the Twins manage to recover from their deadline woes and pick themselves back up with a sweep of the White Sox this weekend, that’ll push the streak to 20 and put them in league with the likes of the inaugural Montréal Expos from 1969 and two separate Philadelphia A’s teams. Speaking of the A’s, that’ll probably be the “best” chance in the near future of the White Sox breaking this streak.

The scare quotes are there for a reason. Here’s a fun fact for everybody at home: While the Oakland Athletics are indeed in last place in the AL West and the second-worst team in the American League at 47-65, they are 18.5 games ahead of the White Sox in the AL standings. That is absolutely mortifying! So while the A’s themselves are pretty bad, they are not moribund like the White Sox are and that could very well turn into a sweep as well. Twenty-three games would put them up there with the 1961 Philadelphia Phillies and give them a tie for the worst losing streak in the modern era. History is well and truly within the grasp of the White Sox at this point but their woes could even get even deeper than that!

If the White Sox are indeed on a 23-game losing streak by this time next week, then they’ll have to steel themselves for what will surely be the fight of their baseball lives. If the streak is still intact, then the record will be on the line at Guaranteed Rate Field against none other than the Chicago Cubs. While the Cubs didn’t necessarily buy or sell at the deadline, one thing that’s for certain is that they aren’t punting on 2024 just yet. They’re going to need every last win they can get if they want to hold on to what’s already a very tenuous shot at getting into the Postseason and you know that everybody in that building wearing Cubbie Blue would love nothing more than to put the nail in the coffin and deal the White Sox their most embarrassing defeat in a while.

If this losing streak gets to 24 games then the White Sox would be all alone in the modern era and would join the 1899 Cleveland Spiders. By that point, it is feasible that this thing could even get all the way up to 30 considering that the Pale Hose would then have to face the New York Yankees and the Houston Astros. It’s highly unlikely to get close to 30 but the fact that it’s even within the realm of possibility is terrifying!

Should this losing streak continue to get worse, then the streak won’t be the only piece of history that the White Sox would be making. They’d also be “chasing” the infamous 1962 Mets for the worst regular season record in a season that went at least 162 games. They’re already behind those Mets in terms of winning percentage and if this streak gets as bad as it possibly could then they could end up being a virtual lock to “surpass” the ’62 Mets and go down in history as the worst team to ever set foot on a Major League Baseball field.

This is a team that was already a complete disaster before the deadline and now they’ve shipped out some of the very few productive members of this team. If I was a White Sox fan then I’d honestly be rooting for the streak to continue. Nobody talks about a team that simply wins or loses 100 games but everybody would be talking about a team that won or lost 120 games. History beckons for the 2024 Chicago White Sox and now it’s up to this organization to either answer the call and become a truly memorable five-alarm tire fire or just a fairly notable halfway crooks in inglorious baseball lore.