How does a team that seemed to be on the rise 10 years ago and won the division three years ago find itself on the brink of the most losses in baseball history?
For the Chicago White Sox, the journey to rock bottom was a series of missteps, misjudgments and missing pieces. They’ve had too many good players land on the injured list, and a series of bad drafts, blockbuster trades that fizzled and short-term deals with no real impact left a roster that might have been in its prime settling for historical infamy instead.
Here are 10 moves over 10 years that help explain how the White Sox ended up in disarray.
Jumping the gun — December 2014
The White Sox of a decade ago weren’t very good, but they weren’t as hopeless as today. The 2014 team lost 89 games but had some good young talent under team control (José Abreu, Adam Eaton, Chris Sale, Tim Anderson). Chicago drafted Carlos Rodón third overall that summer and decided it was time to start winning.
Rather than continuing to build for the future in the offseason, the White Sox committed more than $110 million to free agents David Robertson, Melky Cabrera and Adam LaRoche. They also traded for Oakland A’s ace Jeff Samardzija, who was 10 months from free agency.
The cost for those 10 months of Samardzija: a four-player package headlined by infielder Marcus Semien and starting pitcher Chris Bassitt, each of whom became an All-Star. The White Sox never had a winning record with Samardzija, Robertson, Cabrera or LaRoche on their roster.
A lost lottery ticket — June 2016
The team averaged 85 losses in 2015 and 2016 yet did not attempt to turn the page. They did nothing of substance at the 2015 trade deadline — Samardzija had a bad year, which sapped his trade value — and they tried to reload for 2016 by signing more veterans and trading for two years of third baseman Todd Frazier (a deal that cost them pitching prospect Frankie Montas, who’s since had a lasting career in the majors).
In third place on June 4, 2016, the White Sox made perhaps their most notorious blunder of this era when they traded 17-year-old Fernando Tatis Jr. to the Padres for veteran starter James Shields.
Tatis was in his first year of pro ball and not yet highly touted, but he quickly emerged as one of the top prospects in baseball. This summer, he made his second All-Star team with the Padres, and he’s still just 25 years old. Shields had a 5.31 ERA across 77 outings for the White Sox.
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Fizzled blockbuster No. 1 — December 2016
The White Sox finally committed to a rebuild in the winter of 2016, beginning with a seismic trade that sent Sale to the Boston Red Sox for a four-prospect package headlined by Yoán Moncada (the then-No. 2 prospect in the game according to Baseball America) and Michael Kopech (another top-100 prospect with a massive fastball).
It seemed to be a franchise-altering deal, but Moncada has delivered one excellent season while otherwise struggling with injuries and inconsistency. Kopech didn’t stick as a starter, and he, too, dealt with health and consistency problems before being traded in July. He had a 4.38 career ERA with the White Sox.
The ultimately disappointing return is perhaps magnified by the fact the Red Sox had two third-base prospects worth considering in 2016. Moncada was the biggest name, but the other was Rafael Devers, a top-20 prospect. Preferring Devers over Moncada at the time would have been unusual, but Devers has been an All-Star three of the past four seasons in Boston.
Fizzled blockbuster No. 2 — December 2016
A day after completing the Sale trade, the White Sox sent Eaton to the Nationals for a similarly loaded prospect package of pitchers Lucas Giolito, Dane Dunning and Reynaldo López, all of whom have become mainstays in the major leagues, but none of whom are still with the White Sox. Giolito and López became free agents in November and were traded last July. That return has yet to yield major-league results.
Dunning was traded to Texas in 2020 for starter Lance Lynn, who was traded to the Dodgers last July before becoming a free agent in November.
The Eaton trade was overwhelmingly successful for the White Sox, but its impact didn’t last into this season.
Fizzled blockbuster No. 3 — July 2017
The rebuild continued at the 2017 trade deadline with three notable trades, two of which made little to no impact. Frazier and Robertson were sent to the Yankees for three prospects, two of whom were first-round picks. None had a lasting impact in the majors. The White Sox also traded Cabrera to the Royals for two prospects who never reached the big leagues.
The biggest deal, though, was starter Jose Quintana to the Cubs for a four-prospect package headlined by Eloy Jiménez and Dylan Cease, both top-100 prospects at the time.
Eloy Jiménez was on his way to perpetual stardom with the White Sox before a string of injuries waylaid his career. (Daniel Bartel / Imagn Images)
Jiménez won a Silver Slugger in 2020 and signed a long-term deal when he seemed to be on the verge of perpetual stardom, but injuries took a toll and he became a salary dump at this year’s trade deadline. Cease, too, reached extreme highs on the South Side (second-place Cy Young Award finish in 2022) but went through his own ups and downs before the White Sox traded him to the Padres for four prospects in March.
Cease is among the major-league leaders in strikeouts this season and became the second pitcher in Padres history to throw a no-hitter. Three of the players the White Sox got in return have reached the majors this season, but Drew Thrope and Steven Wilson each have an ERA well over 5.00, while Jairo Iriarte has thrown just three innings with more walks (six) than strikeouts (four).
Draft day disappointments (Nos. 1-4) — June 2015-18
From 2010 to 2014, the White Sox successfully added Sale, Anderson and Rodón as first-round draft picks. From 2015 to 2019, the team’s top picks were Carson Fulmer, Zack Collins, Jake Burger, Nick Madrigal and Andrew Vaughn. All five were chosen in the top 11 overall, and the last two were chosen in the top four. Only Vaughn still plays for the White Sox, and only Madrigal and Burger have a career bWAR better than 1.5 (and Madrigal is more of a utility man than an everyday player).
The players taken immediately after each of those White Sox selections — Ian Happ, Kyle Lewis, Shane Baz, Jonathan India and JJ Bleday — are almost universally higher-impact players. Both Baseball America and MLB Pipeline expected the White Sox to take Brady Singer fourth overall in 2018 (they went with Madrigal instead) and Singer now has a 3.53 ERA in his fifth year as a Royals starter.
Draft Day disappointment No. 5 — June 2019
Of all the White Sox’s recent first-round disappointments, the most striking might be Vaughn. Taken third overall in 2019, he was something of a consensus selection behind eventual All-Stars Adley Rutschman and Bobby Witt Jr. It was not a controversial selection by the White Sox, but it hasn’t been a good one.
That 2019 draft class has proven to be loaded, with 13 first-round picks who have already amassed at least 2.9 bWAR in the big leagues. Vaughn has half of that. The Athletic reported that, leading into the 2019 draft, the White Sox were considering a different option at No. 3: current Nationals All-Star shortstop CJ Abrams. They ultimately went with Vaughn who has a .711 OPS as the team’s primary first baseman this season, and a strong September has pushed his OPS+ to a slightly above-average 102.
Signings to regret — December 2022
For two years, the White Sox seemed at least in some ways to be trending in the right direction. In 2020, Jiménez was a Silver Slugger, Giolito got down-ballot Cy Young Award attention, Luis Robert Jr. finished second for Rookie of the Year, Moncada was mostly healthy, they made it to the wild-card round and the White Sox nabbed current All-Star Garrett Crochet with the 11th pick in the 2020 draft. (Their decision in late October to hire Tony La Russa as manager, however, was controversial at best.) The team returned to the playoffs in 2021, losing 3-1 to Houston in the ALDS. Things weren’t perfect, but they weren’t historically awful.
After finishing 81-81 in 2022, the White Sox tried to address their hole in left field by signing All-Star, Gold Glove winner and World Series champion Andrew Benintendi to a five-year, $75 million deal.
Although he’s been much better in the second half of this season, Benintendi’s first two years in Chicago have produced below-average offensive numbers (90 wRC+) with the second-lowest fWAR (-0.7) among all qualified major-league players. That disappointing production has come as Jiménez, Robert and Moncada have largely failed to live up to long-term extensions meant to stabilize the organization by keeping good young talent throughout its prime.
Limited impact (so far) of another rebuild — July 2023
On their way to 101 losses in 2023, the White Sox began rebuilding again with five deals at last year’s trade deadline. Those trades might pay off but haven’t had much impact yet.
Korey Lee (acquired from the Astros for Kendall Graveman) has been a below-replacement-level catcher, while Jordan Leasure and Nick Nastrini (acquired from the Dodgers for Joe Kelly and Lance Lynn) have ERAs over 6.00.
There remains considerable hope for minor leaguers Edgar Guero and Ky Bush (acquired from the Angels for Giolito and López), and the Sox’s most recent first-round draft picks also look promising (three of them rank among Baseball America’s top 50 prospects), but they’re not ready to help the current team turn things around.
Picking the wrong stopgaps — January 2024
With their roster trending in the wrong direction, the White Sox have not made many win-now investments in the past two offseasons. They’ve signed a few low-cost deals that became useful trade fodder (Keynan Middleton, Erick Fedde, Tommy Pham, Paul DeJong), but their stopgap measures have largely failed.
The White Sox traded reliever Aaron Bummer to the Atlanta Braves this offseason for a quantity-over-quality package of faded prospects and role players, the best of which has been Jared Shuster, a middle-inning reliever. Veterans Kevin Pillar, Mike Moustakas, Martín Maldonado, Brad Keller and Jesse Chavez were signed and ultimately released. Pillar became an above-replacement-level outfielder for the Angels, while Chavez latched on with the Braves and has a 3.13 ERA out of their bullpen. Jake Cousins was traded for cash at the end of March and has a 2.37 ERA with the Yankees. Lefty Tim Hill was released in June and has also become a quality reliever for the Yankees.
As measured by FanGraphs, the White Sox have only two players on their current roster (Crochet and Chris Flexen) who have been worth even 1 WAR this season. While searching in vain for vaguely viable big-league players, the White Sox in January put 27-year-old infielder Romy Gonzalez and 26-year-old reliever Declan Cronin on waivers. Gonzalez was claimed by the Red Sox and has a 103 OPS+ while playing six different positions. Cronin wound up with the Marlins and has a 1.2 fWAR out of their bullpen.
By those measures, Gonzalez would have been the White Sox’s best hitter for much of this season, and Cronin would have been their most valuable reliever. But, of course, that’s not saying much. It’s the kind of thing that happens only when a team unravels — not in a single season, but over many years of missteps, misfortunes and misery.
(Top photo of Chris Sale in 2016: Harry How / Getty Images)
