The 2024 Chicago White Sox are making history for all the wrong reasons. On Monday, they tied the American League record for consecutive losses, dropping their 21st straight game before finally picking up a win on Tuesday night in Oakland.

Nearly three-quarters of the way into the season, the numbers are staggering: a .241 winning percentage that puts Chicago on pace for 123 losses, a 28-88 record that is already 41 games behind first-place Cleveland in the AL Central and a negative-247 run differential that is 70 runs worse than the closest team.

To put it all in perspective, we asked ESPN MLB experts Bradford Doolittle, Jesse Rogers and Jeff Passan to break down the chances the White Sox finish the season with the worst record in MLB history, the clubhouse vibe during their historic struggles and how a team that won 93 games just three seasons ago sunk to this level of woefulness.

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What are the odds the White Sox set the all-time record for losses?

The White Sox are 28-88. Stare at those numbers and think about them. It’s unreal, unfathomable and unthinkable. They are likely going to hit 90 losses before they reach 30 wins. To begin estimating how this might turn out, let’s build our way from historical context, to a glance back at the preseason and an overview of how things have evolved, then peek ahead at what’s left on the schedule.

The White Sox have never been this bad in their 122-year major league history. Already, in the second week of August, my simulations give them a 99.9% chance of breaking the franchise record for 106 losses set in 1970 — back in the days of Bill Melton, Tommy John and Wilbur Wood. To avoid breaking that mark, they’d have to go at least 28-18 from here, and even after they snapped their epic 21-game losing streak, it seems highly unlikely that the White Sox have 28 wins left in their 2024 future.

With local ignominy a virtual cinch, we can then wonder about even more enduring and undesirable fates. Namely: Are the White Sox really in the conversation as the worst team of all time? Very much so.

Back in the preseason, I was convinced that this was a really bad team. My final preseason forecast was for a quaint 101 losses that pegged them as the worst team in the American League. Little did I know that my forecast was wildly optimistic.

By the third week of April in the midst of a 2-15 start, my simulations already had their forecast down to an average of 50.1 wins. They rallied just a little but by late June, the average was under 50 wins and has just kept getting worse. As we publish this, their average win total in the simulations is a surreal 42.3 wins which, to flip the perspective, translates to 119.7 losses. This is a historically awful team.

It gets worse. The simulations are based on a season-to-date performance and a going-forward evaluation of their depth chart for the rest of the season. For Chicago, that depth chart got decidedly weaker at the trade deadline and from the beginning of July until now, the baseline measure of the White Sox roster has dropped by more than five wins, from just over 55 to barely over 50. Some of that is the accelerating losing percentage, but just as much is due to the hollowed-out roster.

To go 43-119 and avoid matching the 1962 Mets’ loss record, the White Sox need to go 15-31 — a bad winning percentage (.326), but is quite a bit better than what Chicago has done so far. The remaining schedule is unremarkable in either direction. The White Sox have around an even number of home and road games left, though at this point, it’s hard to say they’d glean much advantage by playing at home more often. The aggregate quality of their remaining opponents is exactly average, translating to that of an 81-win team.

When you take those factors, the White Sox’s sinking baseline and their average remaining schedule, the simulations are not kind. As mentioned, the average win total comes out to 42.3, but the meat is in the distribution of those sim-by-sim win totals. And that’s this:

Probability of a franchise-record 107 or more losses: 99.9%.
Probability of a modern era record of 121 or more losses: 41.9%

Finally, there are a couple of more benchmarks to keep in mind. The Mets hold the modern day loss record, as we know. The all-time loss record, including the dusty bins of the 19th-century big league archives, is 134, by the infamous and unfortunate 1898 Cleveland Spiders. Well, the White Sox would have to lose every remaining game to beat match that. It … won’t … happen?

More realistic is the record for lowest single-season winning percentage, which is currently the .23504 by the 1916 Philadelphia Athletics, who went 36-117 with a tie. The White Sox, currently at .24138., can definitely get there. The win total to watch is 39. If Chicago gets there, it avoids that record. If it ends up with 38 wins or less, it lessens Connie Mack’s historical burden by one large item.

And according to the sims, the White Sox have a 14.2% chance at 38 or fewer wins. It doesn’t get any more grim than that. — Bradford Doolittle

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What is the vibe like in the clubhouse as the losses pile up?

Believe it or not, it could be worse. In fact, the mood around the team felt even more downtrodden last season when the team was actually expected to compete before going 61-101. Guys are going about their business before games just like any team would but once the competition begins, there is no life to this version of the White Sox. Players have still been accountable after losses, but Chicago has been so bad for so long that there really are no outward signs of anger. There is frustration though, mostly showing on the faces of the hitters in a lineup that has wholly underachieved. It’s a veteran group that has gotten along much better than last year, but hasn’t produced on the field. Tommy Pham described one frustrating aspect for this season’s lineup after being traded from the White Sox to the St. Louis Cardinals at the deadline.

“It’s unfortunate we blew so many leads because that changes what kind of reliever the other team brings in,” Pham said. “So many times my fourth at-bat was against the other team’s best instead of a guy they were going to bring in when trailing. I don’t blame anyone. It’s just frustrating for the hitters.”

Everyone wearing a uniform understands how demoralizing it can be in a clubhouse when a team keeps blowing leads. The rotation has been the lone bright spot but saw so many quality appearances by Garrett Crochet, Erick Fedde (before he was dealt to St. Louis) and others wasted by the bullpen. According to ESPN Stats & Information, the White Sox own the worst winning percentage (.391) this season in games in which they’ve led and the second-worst mark of any team since 1990. Chicago has blown 42 leads while no other team in the majors has blown more than 30. In fact, the White Sox have blown the most one, two and three-run leads in MLB.

It’s hard to imagine any clubhouse surviving all of that.

Then there is manager Pedro Grifol, whose own future with the franchise is murky. One example of Grifol failing to connect with his clubhouse came in May, when Orioles starter Kyle Bradish shut out the White Sox over seven innings. The team was simply overmatched, but the second-year manager chose to call them out afterwards saying players were “f—ing flat.” It rubbed many in the organization the wrong way.

There’s a joylessness to the White Sox. Losing certainly accentuates it, but the vibe has been hovering over the team for nearly two seasons. — Jesse Rogers

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How did they possibly get this bad — and is there a way out of it anytime soon?

Everything looked so good four years ago. The White Sox had embarked on a full-tank rebuild, and it was beginning to bear fruit. The Chris Sale trade, which kicked off Chicago’s descend-to-ascend strategy in December 2016, landed it arguably the best prospect in baseball (third baseman Yoan Moncada) and one of the most talented arms (Michael Kopech). A day later, the White Sox stole right-hander Lucas Giolito in a trade for Adam Eaton. Eight months after that, the Jose Quintana trade secured Eloy Jimenez, who would establish himself as a top-five prospect in MLB, and Dylan Cease, a strikeout machine on the mound. They signed Cuban standout Luis Robert Jr., took Nick Madrigal and Andrew Vaughn with top-five picks in the draft, watched Tim Anderson blossom into a batting champion, still had Jose Abreu and rightly believed they possessed the best young core in the American League, if not all of baseball.

And they weren’t wrong. It’s easy to forget now, but the White Sox were a good baseball team this decade. They made the postseason in 2020 and won the AL Central in 2021. But there were signs that perhaps not all was well. And soon enough those signs were flashing with the luminosity of Vegas neon.

Moncada regressed. Kopech wasn’t a starter. Giolito was inconsistent and Jimenez always hurt. Robert never played a full season, either. Neither Madrigal nor Vaughn reached their pick’s expectations. Anderson cratered. Everything that was supposed to be wasn’t. It was a staggering player-development failure, though the White Sox’s issues go far beyond the inability of individuals to manifest excellence and is as much a function of a culture that starts at the top of the organization.

Owner Jerry Reinsdorf’s decision to hire his friend Tony La Russa as manager before the 2021 season illustrated everything that is wrong with the White Sox. To turn to someone who hadn’t been in a major league dugout in nearly a decade, during one of the most transformative periods in baseball history, and expect him to sprinkle pixie dust on the operation ignored that the White Sox were trying to stuff a Ferrari engine into a Yugo frame.

Reinsdorf never invested the necessary money into building the robust analytics and player-development systems of the best teams, and so the infrastructure necessary to ease La Russa’s transition back onto the field was nonexistent. Regardless of his voluminous baseball knowledge, La Russa was set up to falter. It didn’t help that he made nonsensical decisions like intentionally walking a batter facing a 1-2 count. Or that he looked like he was falling asleep in the dugout during a game. Reinsdorf’s desire to right his decades-old mistake of firing La Russa turned out to be an even more egregious error. Making decisions for bad reasons tends to make for bad decisions.

Beyond that, Reinsdorf committed a cardinal sin for rebuilding teams: He didn’t complement his young core with impact free agents. During the 2018-19 winter, the White Sox attempted to sign Manny Machado and spoke with Bryce Harper. They whiffed on both. The most the White Sox have ever spent in free agency is the disasterpiece of a $75 million deal given to outfielder Andrew Benintendi. The only teams to spend less on a single free agent are a who’s who of small-market teams: Oakland Athletics, Pittsburgh Pirates, Tampa Bay Rays, Cleveland Guardians, Cincinnati Reds and Kansas City Royals. The White Sox, as a reminder, play in Chicago.

Still to suggest this terrible, horrible, no-good, very bad season guarantees more to come is flawed thinking. The Royals were 56-106 last year. Through canny free agent signings and strong development of core players, they’re currently 63-52 and own the last wild-card spot in the AL. If Reinsdorf expands the White Sox’s budget and general manager Chris Getz hits on more signings like he did with Erick Fedde, Chicago’s doormat status can be shorter-lived than expected.

The White Sox need to crush the eventual trade of ace Garrett Crochet this winter and turn Robert into something substantive, too. They need Drew Thorpe to pitch like the carrying piece in the deal that sent Cease to San Diego and for other trade acquisitions — right-handers Jairo Iriarte and Nick Nastrini, left-handers Ky Bush and Jake Eder, catcher Edgar Quero and the return for Fedde, infielders Alexander Albertus and Jeral Perez — to develop. They need Noah Schultz to keep throwing like the best left-handed pitching prospect in baseball and for shortstop Colson Montgomery to shake off his .207/.326/.372 line at Triple-A and once again resemble a foundational piece.

It’s a lot to ask. The White Sox aren’t on pace to be the worst team in history by accident. Institutional rot pervades the organization, and it starts at the top. And until things differ there — either via approach or wholesale change — it’s bound to be more of the same.