The MLB Trade Deadline Could Be Dictated by One of the Worst Teams Ever

On Thursday night, two unsurprising, interconnected events transpired in Major League Baseball: Contending teams started making major moves in advance of next week’s trade deadline, and the Chicago White Sox lost.

The deadline is next Tuesday at 6 p.m. ET, so it’s about time teams swung into action and fueled the flames of hot stove grill season. The free-falling Mariners, suddenly a game behind the division-leading Astros in the American League West, sent two prospects and a player to be named later to the Rays for outfielder Randy Arozarena. The Diamondbacks, a game behind the Padres in pursuit of the National League’s third wild card, dealt a pair of prospects to the Marlins for reliever A.J. Puk. And on Friday, the Red Sox, a game beyond the Royals in the race for the AL’s third wild card, traded for Dodgers starter James Paxton. Bubble teams trying to get better by addressing deficiencies; long shots and cellar dwellers restocking for the future. Pretty standard stuff.

As for the South Siders, their 2-1 loss to the Rangers was their 11th defeat in a row. This is the second Sox losing streak of 2024 to reach double digits: They dropped 14 consecutive contests from May 22 through June 6. These Sox are the seventh team in the 30-team era to suffer two streaks of 11-plus losses in the same season, and they’re worse than the previous six. At 27-78, the Sox surprise people when they win, not when they lose.

What is surprising is the part the Pale Hose are positioned to play in MLB’s trade activity between now and Tuesday. The White Sox may be one of the worst teams of all time, yet they employ some of the market’s most appealing players. Rarely has a team been this terrible—and rarely has a terrible team had this much talent to trade. If they decide to fully fold their losing hand, the Sox could dictate the course of the deadline—and, by extension, the rest of the MLB season—more than any other sad-sack club ever has.

It’s always difficult to forecast trade activity, but this year’s deadline may be on the slow side because—as expected—few teams are totally out of contention. Even compared to the two prior campaigns with the 12-team playoff format, this year’s cluster of potential postseason qualifiers stands out. Entering Friday’s games, four days before the deadline, only seven teams are six or more games out of the closest playoff spot, compared to 12 four days before the deadline in 2022 and 10 last year. Some teams within that six-game range have already moved a veteran (the Rays), declared a focus on the future (the Cubs), or dangled their top pitchers (the Tigers), but potential buyers still outnumber potential sellers, and the demand for external reinforcements outstrips supply. Consequently, the clubs that are clearly on the “sell” side of the trade divide could command strong returns. The White Sox are one of them.

Earlier this month, CBS Sports ranked 30 players who seemed likely to be dealt by the deadline. Six of them were White Sox. On an MLB Trade Rumors list of the top 50 trade candidates compiled a few days later, three Sox cracked the top 12, six appeared in the top 25, and seven made the top 40. In Jeff Passan’s deadline preview, published this week, the ESPN MLB insider wrote that the Sox “are listening on everyone, and they’re the odds-on favorite to make the most deals.” On Wednesday, general manager Chris Getz said, “There’s a lot of interest in players on our major league club. And we’re prepared to go in a lot of different directions.”

It makes sense that the Sox would be sellers; their playoff odds, per FanGraphs, flatlined at 0.0 percent on April 7. But it barely computes that they have so much to sell. In Garrett Crochet and Erick Fedde, the Sox employ two of the top five pitchers in baseball, by Baseball-Reference wins above replacement. Luis Robert Jr. missed two months this spring with a hip flexor strain, but he’s a plus center fielder with speed and power who hasn’t yet turned 27. Several other more marginal players round out the club’s potential trade bait—closer Michael Kopech, setup men Tanner Banks and John Brebbia, outfielder Tommy Pham, and first baseman Andrew Vaughn. As Passan noted, “anything is on the table.” And the table is astonishingly full.

“Astonishing” might sound hyperbolic, but only if you haven’t watched the White Sox. Only 10 previous AL and NL teams in the “modern” era (since 1901) have won 27 games or fewer in their first 105—and all but one of them played before the U.S. entered World War II.

The lone, infamous exception is the 1962 Mets, an expansion club that went 40-120-1. The Sox are on pace to lose 120 too, which would tie those Mets for the most team losses in the modern era.

As one would expect, given their record, the Sox aren’t good at anything. Their mediocre rotation is their (relative) strength, thanks in large part to Crochet and Fedde. Their bullpen is merely bad. Their lineup is truly atrocious. No team in the majors has scored fewer runs per game in a full season since the AL added the designated hitter, and only one team since the dead-ball era (the 1965 Mets) has had a lower on-base percentage than Chicago’s current .277. Adjusting for this season’s low-offense environment makes the Sox seem slightly less inept, but their wRC+ and OBP relative to the league would still be the worst in a non-shortened season for any team with a DH.

Granted, the Sox have been unlucky in addition to being bad: They’ve played a tough schedule, they’ve gone 8-22 in one-run games, and they’ve deserved to win eight more games than they have, if you believe their BaseRuns record. FanGraphs projects a .417 winning percentage for them the rest of the way, which would result in a 51-111 record for the season. That seems … optimistic, not least because it presumes that Chicago will keep the three players on its roster (Crochet, Robert, and Fedde) who are individually projected to amass more than 0.5 FanGraphs WAR in the games to come. By Baseball-Reference’s accounting, that trio has produced 10.0 WAR so far, while the entire team—including Crochet, Robert, and Fedde—has collectively accumulated 4.2. A little arithmetic will tell you what that means for the rest of the roster.

If the Sox were to trade all three of those players and no one else, they would rank among the most prolific deadline dealers ever. The table below lists all the teams that dealt more than 6.0 combined year-to-date WAR during the two weeks leading up to the trade deadline, along with those clubs’ win-loss records as of deadline day. The full list dating back to 1921 (the first year to feature the same deadline in both leagues) is available here, courtesy of Kenny Jackelen of Baseball-Reference. (From 1923 through 1985, the trade deadline was June 15; in those years, teams typically played a little more than half as many pre-deadline games as they have since the deadline was pushed back by several weeks in 1986, and thus the pre-deadline WAR totals in that era tended to be a lot lower.)

There are no winning teams in that table because winning teams generally try to add, not subtract. But there aren’t many abysmal teams, either. Those 21 squads sported a combined .430 winning percentage at the deadline—approximately a 70-win pace over 162 games. That’s bad enough for them to have given up hope of a playoff appearance, but good enough for them to field players competitive teams would want. If we lower the bar to teams with a .350 or worse winning percentage at the deadline—very bad, but still much more successful than these Sox have been!—then the YTD totals of traded players drastically drop off. The only qualifying club that moved almost as much production as these Sox could was the 2018 Orioles, who parted with Manny Machado, Kevin Gausman, Zack Britton, and others. The O’s would be awful for a few more years but would emerge from their rebuild with the strongest farm system since … well, the late–2010s White Sox. Oof.

The White Sox should be too depleted to have so much coveted talent left. They already sucked and sold in 2023: Only the Mets moved more year-to-date WAR at last year’s deadline, when the Sox off-loaded Lucas Giolito, Jake Burger, Kendall Graveman, Reynaldo López, Keynan Middleton, Joe Kelly, and Lance Lynn. Then, over the offseason, they shipped out Aaron Bummer, Gregory Santos, and, in March, Dylan Cease, who’s had a strong season in San Diego (which he continued by no-hitting the Nationals on Thursday). The rest of the core of the 2020-21 teams that made the playoffs in back-to-back years for the only time in franchise history has either declined (Vaughn, Eloy Jiménez, Yoán Moncada) or declined and departed (José Abreu, Tim Anderson, Yasmani Grandal, Carlos Rodón).

However, the Sox held on to Robert, whom they signed to a team-friendly six-year, $50 million contract—which included two team options—in early 2020. (The two options could keep Robert under team control through 2027, his age-29 season.) At the Winter Meetings, they signed Fedde, who had overhauled himself en route to a 2023 MVP award in Korea, to a two-year, $15 million deal that seemed smart before the season started and seems smarter now. And they shifted the fragile but skilled Crochet, their first-round pick in the 2020 draft, from the bullpen to the rotation, upping his workload dramatically despite the elbow and shoulder injuries that had cost him all or most of the 2022 and 2023 seasons, respectively. The Fedde signing and Crochet conversion have hugely surpassed projections, which is how the Sox wound up with three tantalizing talents even after initiating a teardown.

Just because the ChiSox can dominate the deadline to a degree no other woeful team ever has doesn’t mean they will. As Passan pointed out, “There is a chance Chicago holds on to one (or all) of its most valuable trade chips and moves them come the offseason.” Although trading Crochet would be a classic sell-high move, it’s complicated. Not only has Crochet already blown by his previous single-season innings high, placing his durability in additional doubt, but he reportedly prefers strongly to stay in the rotation—and would be willing to pitch into October only if he signs an extension beforehand. That request/demand could be a bluff, but it might still dissuade teams from parting with top prospects to acquire him. If Crochet’s suitors don’t meet Chicago’s price, the Sox could dangle him again over the winter or talk themselves into getting good again before he’s gone. (Crochet, who turned 25 in June, can become a free agent after the 2026 season.)

One way or another, the Sox—and their fans—face a fraught few days. When White Sox owner Jerry Reinsdorf promoted Getz from director of player development to GM last August, the now-88-year-old Reinsdorf said, “We want to get better as fast as we possibly can.” Stripping the roster down to the studs could conceivably hasten that process. The Sox’s sell-off has already paid prospect dividends: Their FanGraphs farm system ranking has climbed from 30th entering 2022, to 27th entering 2023, to 11th entering 2024, to fifth today. If the Sox go all out at the deadline while the Orioles go all in, the former could complete a climb from worst to first on the farm in less than three years.

Of course, that’s small consolation, considering they’ve already fallen from “first in the AL Central” to “worst team in baseball” in three years. As Neil Paine observed this spring, only one team has ever fumbled its future—in terms of actual WAR accrued over the following three years, compared to its expected total based on past production and team age—more glaringly than the 2021 White Sox: Connie Mack’s mid-1910s A’s. Those A’s won the World Series in 1913, lost the Series in 1914, and then touched off a fire sale so scalding that the 1915 team plummeted to 43 wins, and the 1916 team (which appeared toward the top of the first table above) sank to 36. The Sox are far past the point of waving a White Flag Trade, but whatever they do (or don’t do) will unfold against the backdrop of their failure to sustain their winning ways after the last time they bottomed out and built back up—and amid Reinsdorf’s threats about the team’s potential departure if it doesn’t receive a massive subsidy to build a new ballpark.

If the Sox seize this seller’s market, they may be glad they did down the road. In the meantime, though, they’ll increase their odds of making hapless history with 120-plus losses, and they’ll rob their suffering fans of their last few reasons to buy tickets or tune in (aside from rookie righties Drew Thorpe and Jonathan Cannon). No wonder the Sox faithful feel conflicted, to the extent they still feel anything. Jim Margalus, founder and managing editor of Sox Machine, a leading independent source of Sox coverage, says the fan base is beset with “pervasive ennui because no decision-makers in the White Sox organization deserve any benefit of the doubt.” Margalus adds:

They already played the rebuild card, so that well is poisoned. Reinsdorf doesn’t spend money to make money, so nobody expects the Sox to pull an early-aughts Tigers and brute-force their way out of it. Everything rests on the Getz administration being better evaluators of talent than Kenny Williams and Rick Hahn, and so far, his body of work is a roster that could be the worst team in modern major league history. … So what’s left is rooting for individual players without any real faith that they’ll be a part of the next good White Sox team, or that the front office has the ability to trade them for players who might be. … When the front office can’t be trusted to get or develop a commensurate return, then why not keep the good player so there’s somebody to watch?

“The next several days are going to be very interesting,” Getz said this week, describing himself as “open-minded” and “highly motivated to solve this puzzle of putting the White Sox where they need to be.” The solution he settles on won’t just determine where a few player pieces slot in. It could direct the whole dang deadline.