15 worst trades in Chicago White Sox franchise history

The Chicago White Sox have been one of the most storied franchises in Major League Baseball over the course of their century-long life.

With three World Series titles, six American League pennants, and a whole lot of star power both at the plate and on the mound, there's no doubt that this club is one of the greatest franchises in the sport's history.

Like all other teams, there have been a ton of moving parts in this organization, with many players coming in and out on a seemingly daily basis. Many trades have come together over the years but it was until more recently that the White Sox began to lose trades more than they won.

Under general manager Rick Hahn, the Sox have gone through a few full teardown rebuilds and seen an abnormal amount of veterans shipped off for prospects that will hopefully be contributors down the line. More often than not, these deals have blown up in his face.

I think it's rather obvious which deal is going to take the top spot in this ranking, but what about the other 14 slots? Unfortunately, most of these deals have been made under Hahn's rule, with only a small group of them coming from the pre-Hahn days.

Let's take a look back in time and break down the worst 15 trades in Chicago White Sox history:

No. 15: Melky Cabrera and cash traded to the Kansas City Royals for A.J. Puckett and Andre Davis - July 2017

By the time Melky Cabrera came over to the White Sox, he had already wrapped up his prime years in Major League Baseball.

A switch-hitter who saw some extreme highs and lows throughout his career, he signed a three-year, $42M contract heading into the 2015 season and gave the Sox a veteran presence to help guide the team through some rebuilding years.

He was actually still a pretty great hitter when he was with the Sox, as he hit 39 home runs in 407 games with a .287 average and 108 OPS+, so he did exactly what the club wanted him to do.

However, it's the package the White Sox got in return for the longtime veteran that warrants a spot on this list.

Chicago sent Cabrera packing to the division rival Kansas City Royals, even including $2.5M in cash to help the Royals with the financial part of the deal. Neither of the two pieces heading from the Royals to the Sox ever even made the major leagues.

A.J. Puckett, now 27, played in a total of five games at the White Sox's High-A affiliate before going M.I.A. for two years thanks to Tommy John surgery.

He was selected by the Atlanta Braves in the minor league Rule 5 Draft in December of 2020 and wrapped up his White Sox tenure with 27 innings to his name.

Andre Davis, the other pitcher moving from Kansas City to Chicago, made just four appearances for the A-ball Kannapolis Intimidators, posting a 2.84 ERA over 12.2 innings before never playing another inning in professional ball, making this trade a total dud.

No. 14: Konnor Pilkington traded to the Cleveland Indians for César Hernández - July 2021

This trade is still in the process of shaking out in present day, so it will reside near the bottom of this list for now.

When the White Sox were acquiring Hernández, they thought they were going to be landing a contact-oriented hitter who found his power stroke in recent years, swings the bat from both sides of the plate, is a former Gold Glove Award winner and a known clubhouse leader.

Instead, they received the shell of what Hernández once was. A pending free agent, he was a rental acquisition that did virtually nothing for the Sox.

In 53 games post-trade, he went just 45-for-194 (.232 average) with just seven of those hits going for extra bases. He limped to the finish line with an OPS+ of just 68, meaning he was 32 percent below league-average offensively for the Sox.

His struggles didn't even stop there, either. He also posted a -0.3 dWAR along the way, no longer possessing a Gold Glove-caliber glove as he once had.

While a mid-season rental struggling is not enough to warrant any real concerns. it's what Pilkington has done for the (now) Guardians since the trade.

He made his big league debut last year and looked very solid, making 15 appearances (11 starts) and posting a 3.88 ERA and 99 ERA+. He limits home runs at an impressive rate and figures to see some time in the major leagues in the upcoming season.

If Pilkington continues to develop, this trade will come to hurt the Sox for many years to come, especially because he'll be doing it for a division rival.

No. 13: Anthony Swarzak traded to the Milwaukee Brewers for Ryan Cordell - July 2017

We're three trades in and already have our second entrant from the 2017 trade deadline (spoiler alert: it's not the last).

Swarzak, a longtime member of the Minnesota Twins and former Cleveland Indian, joined the White Sox in 2017 and was a major bright spot on a horrendous 2017 team.

In 41 games, the then-31-year-old had a 4-3 record with a 2.23 ERA, 2.35 FIP, and 193 ERA+, what ended up being the highest mark of his 11-year career.

Swarzak, like Hernández, was a rental. So his loss never made shockwaves through the organization. But the player the Sox got back, an intriguing outfielder who was meant to be a solid contributor, is the sole reason for this deal's inclusion on the list.

Cordell, a highly-touted prospect who had 20 HR/80-90 RBI potential and also possessed some wheels on the bases, had previously been a part of the Jonathan Lucroy deal that sent the All-Star catcher from the Brewers to the Rangers.

After hitting 18 doubles and 10 home runs in 69 games for the Brewers Triple-A affiliate in 2017, Cordell figured to be a young and promising outfielder that the Sox could slot into their rebuilding lineup and see if they can uncover something great.

Instead, he missed the rest of the year with an injury and when he did make it to the big leagues, he had a combined .205 batting average and 61 OPS+ in 116 games for the Sox, giving them one of the worst players they've ever had.

No. 11: Danny Darwin, Wilson Álvarez and Roberto Hernández to the San Francisco Giants for Brian Manning, Lorenzo Barceló, Mike Caruso, Keith Foulke, Bob Howry and Ken Vining - July 1997

Infamously known as "The White Flag Trade", this blockbuster was negatively received by fans of the White Sox when it went down. The team was only 3 games out of first place, after all, so it's easy to understand why there's so much hate.

Going out the door was starting pitcher Danny Darwin, who had been worth 1.5 bWAR through the first 21 appearances of his White Sox tenure (at the age of 41 nonetheless!); Wilson Álvarez, who had been an above-average starter for the club the past seven years and Roberto Hernández, the club's closer.

This monster of a deal saw a massive chunk of the White Sox's pitching staff go out the door and a full-blown rebuild begin.

Starting off with the incoming player who contributed the least to the White Sox, outfielder Brian Manning never even made it to the big leagues with the club, retiring at the tail end of the 1999 season at 24 years old.

Barceló made 43 relief appearances for the club over the next three seasons, posting a combined 109 ERA+ along the way. He never amounted to much, but he was nine percent above league-average at that time.

Vining, a left-handed reliever, made eight appearances for the Sox in 2001, allowing 13 earned runs in 6.2 innings of work, walking seven, and striking out only three.

Caruso, a middle infielder, played 269 games for the Sox in two seasons but was one of the least productive batters of his time and was also an awful baserunner. He led the league in failed stolen base attempts with 14 in 1999.

What keeps this deal away from the top of this list is the acquisitions of Howry and Foulke. Both of these players were relief weapons for the White Sox. Howry stayed in Chicago for five years and had a combined 3.74 ERA and 127 ERA+ in 322 innings of work.

Foulke was even better, playing six years for the team and posting a 2.87 ERA and 166 ERA+ in 446 innings of work. Neither of them was around for much winning from the White Sox, but they both performed exceptionally well for the team during their time.

No. 10: Nick Madrigal and Codi Heuer to the Chicago Cubs for Craig Kimbrel - July 2021

It's hard to blame Rick Hahn for making the attempt here. After all, Kimbrel is one of the best relief pitchers in the history of the game.

The only thing questionable about this is the fact that he wasn't acquired a few years sooner. Kimbrel had been in the midst of a rough two-year stretch before re-emerging as a dominant closer on the Cubs prior to the trade.

The then-33-year-old had allowed just two earned runs in 36+ innings of work for the Cubs, good for an ERA of 0.49 and ERA+ of 865. Yes, he was 765 percent above league average to start the year.

With the White Sox, he made 24 appearances and stumbled to the finish line with a 5.09 ERA and 87 ERA+ across 23 innings of work. He looked much more like the 2019 and 2020 versions of himself than he did in his Braves days.

Madrigal was the big piece going from Chicago to Chicago here, as he was the No. 3 prospect in the White Sox system in 2021 per MLB.com. He had performed well with the Sox in 83 games prior to the trade, posting a .317 average and 109 OPS+ while sitting around average on defense.

With the Cubs, he doesn't seem to have a spot on the active roster, so his potential is very much being wasted. Instead, Heuer is going to end up being the piece the White Sox will miss the most.

He had shown some flashes of brilliance before the trade and he did struggle to start his Cubs tenure, but he looked like the real deal last year.

In 25 appearances last year, Heuer posted a 3.14 ERA and 136 ERA+ across 28+ innings of work. He was supposed to be a key contributor out of the Cubs' bullpen in 2023 but he is recovering from Tommy John surgery and is likely going to miss (at the very least) half of the upcoming season.

No. 9: Todd Frazier, David Robertson and Tommy Kahnle to the New York Yankees for Blake Rutherford, Tito Polo, Tyler Clippard and Ian Clarkin - July 2017

Yet another massive trade involving multiple longtime veterans and a whole lot of prospects. Just like the White Flag Trade, this one did not work out for the Sox.

Frazier, Robertson, and Kahnle all had established themselves as stars prior to joining the White Sox and each of them was expendable once the awful 2017 season began to unfold. This is another one that's hard to blame Rick Hahn for trying, but the return was just atrocious for the club.

As a matter of fact, only one player acquired by the White Sox in this trade played a single inning in the big leagues for them. Clippard, one of the more durable and respected relievers in the game, posted a 1.80 ERA in 11 games before being flipped to the Astros less than a month later.

Clarkin was supposed to be a solid left-handed starting pitcher but he struggled to stay consistent while in the Sox system and never made it past Double-A for the club.

Polo, a speedy outfielder, also struggled to find consistency in the organization. His only full year for the Sox was in 2018 when he made 53 appearances, registering 47 hits but just 13 extra-base hits. His average that year was .254 and he was cut loose at the end of that year.

Rutherford actually stayed in the system until the end of the 2022 season. He displayed occasional promise in his rise through the organizational ladder but he had a hard time with strikeouts and spent two seasons in Triple-A before becoming a minor league free agent at the end of the year.

He recently signed a minor league deal with the Washington Nationals, officially putting an end to this trade tree and cementing its place as one of the worst ever by the Sox.

No. 8: Alex Call to the Cleveland Indians for Yonder Alonso - December 2018

This trade is not so much about the results as it is about the premise behind it. Amongst the Manny Machado free agent craze, the White Sox front office actually thought that signing Alonso, his brother-in-law would guarantee Machado signing in Chicago.

We all know how this ended. Machado, of course, wound up signing a gigantic 10-year, $300M contract with the San Diego Padres, and the White Sox were left with nothing but an aging, declining first baseman who couldn't hit a baseball off of a tee while he played for them.

As a matter of fact, 2019, Alonso's first and only with the club, wound up being his last in the majors. He made it into 67 games for the Sox, hitting seven home runs and driving in 27 with a batting average of .178 and an OPS+ of 55.

There's no doubt about it, the Sox brought aboard one of the worst hitters in the game to maybe sign Manny Machado. Didn't work.

Prior to the trade, Call had been a decent but not great outfielder that steadily was rising through the ranks for the Sox. He was never projected to amount to much and had only reached double-digit home run totals once in his three years there.

He broke into the majors last year with the Guardians, appearing in 12 games before being designated for assignment and later claimed off of waivers by the Washington Nationals, where he remains today.

No. 7: Bobby Bonilla to the Pittsburgh Pirates for José De León - July 1986

Bonilla is now best known for the ridiculous contract that he signed with the New York Mets. However, many have forgotten that his storied career began all the way back in 1986 with the White Sox.

After being selected in the Rule 5 Draft from the Pirates by the Sox, Pittsburgh came back around and traded for the eventual All-Star. Of course, his career began to really take off once he left Chicago.

After returning to Pittsburgh, Bonilla made four straight All-Star Games and emerged as one of the game's top offensive players. He went on to have a highly successful 16-year career, performing well at every non-White Sox stop along the way.

De León never amounted to much with the White Sox, making this trade a loss through and through. He looked sharp in 13 starts after the trade but his first full season with the club saw him post an ERA north of 4.00 with nearly 100 walks.

He was flipped to the Cardinals in 1988 and did ultimately return to the White Sox in 1995, but his lack of noteworthy performance makes this deal a tough one since Bonilla experienced so much success after leaving Chicago.

No. 6: Three-team trade between the White Sox, Dodgers, and Reds - December 2015

This deal had so many moving parts that it needed its own trade graph.

Yes, you are reading that right. The White Sox traded away Frankie Montas, an eventual top-of-the-rotation talent, for Todd Frazier.

To be clear, the loss of Montas is the sole reason why this deal is so high up on this ranking. Johnson is now out of the league after being worth -0.9 bWAR in parts of three big league seasons.

Thompson, now 32, is still active and is projected to make the Dodgers' Opening Day roster. He has been around the league for six years now, bouncing around between multiple different clubs, but has never had as big of a shot at everyday playing time as he does in 2023.

The White Sox moved on from him after he hit five home runs with a .295 average and 147 OPS+ in 2015.

Montas, now a member of the New York Yankees, made just seven appearances for the Sox before he was sent packing in favor of Frazier. Of course, after the deal went down he emerged as an ace-level pitcher for the A's.

He went on to play six years in Oakland, posting a 3.70 ERA in 114 appearances with a 111 ERA+. He's one of a few future star pitchers that the Sox let go of too early.

To Frazier's credit, he waited until he joined the White Sox to start displaying the best power numbers of his career. He hit 40 home runs in 2016 and drove in 98, both career highs, but he was a part of such terrible White Sox teams that his production did nothing to help the club succeed.

No. 5: Sammy Sosa and Ken Patterson to the Chicago Cubs for George Bell - March 1992

By the time Bell came over to the White Sox, his career was winding down. He had become a Toronto Blue Jays legend, winning the first MVP Award in franchise history and making two All-Star Game appearances as well.

Once he came to Chicago, he appeared in 257 games for the Sox, hitting 38 home runs with 176 RBI and an OPS+ of just 84. The White Sox were getting a completely different player than the Bell of years past.

Patterson had become a reliable relief pitcher for the White Sox prior to the trade, appearing in 145 games over four years with the club. He had a 3.70 ERA and 106 ERA+ in 216 innings as a White Sox before moving to the Cubs.

His career numbers never came close to what they were pre-trade, which helps a little bit, but he's not the big loss in this deal.

That would be Sosa, who emerged as one of the most fearsome power hitters the game of baseball has ever seen.

By now, everyone knows what he was able to accomplish as a member of the Cubs. Seven All-Star Games, six Silver Slugger Awards, the 1998 NL MVP Award, and much more. The loss of Sosa will forever go down as one of the harder ones for White Sox fans to swallow.

No. 4: Gio González, Fautino De Los Santos and Ryan Sweeney to the Oakland Athletics for Nick Swisher - January 2008

González and De Los Santos were traded away from the White Sox before appearing in a single game for the big league squad. Of course, De Los Santos never amounted to much for the A's, but González went on to become a star-level pitcher for Oakland.

Just two years after the trade, he won 15 games for Oakland. The following year, he won 16. The year after that? He won 21 games and finished third in the Cy Young race. Even after he moved on to the Washington Nationals for a seven-year stretch, he was still one of the more durable and successful lefties in the league.

Sweeney, the lone member heading out the door that had already made his big league debut, had promise, but couldn't deliver on it over the course of his nine-year career. The loss of him and De Los Santos never hurt much, but González would've looked great atop the White Sox rotation over the years.

Swisher, already covered in another part of this piece, stuck around in Chicago for just a single season. He hit 24 home runs but had an OPS+ of just 93 in 2008 before being traded once again to the Yankees. The White Sox effectively turned Gio González into two awful pitchers and an awful utilityman. This deal is nothing but pain.

No. 3: Rich "Goose" Gossage and Terry Forster to the Pittsburgh Pirates for Richie Zisk and Silvio Martínez - December 1976

This deal is yet another one that makes at least a little bit of sense, but ultimately wound up a loss for the White Sox.

At the time of this deal, Gossage had made himself known as one of the better pitchers in the game, finding success as both a starting pitcher and closer all while being 24 years old and younger. In parts of five years, he had a 3.80 ERA and 97 ERA+ across 188 games and 584+ innings.

His low ERA+ is largely thanks to the first few years of his career. He made the All-Star Game in each of his final two years in Chicago.

Forster had been a versatile pitcher for the Sox as well, also starting and closing games at some point throughout his six-year tenure on the club. He had a 3.36 ERA and 111 ERA+ in 263 appearances and 605 innings before the trade.

On the other side of things, Zisk had made himself into one of the more dynamic power hitters in the game for Pittsburgh. He finished ninth in the 1973 Rookie of the Year standings and twice earned NL MVP votes during his six-year tenure.

Along the way, he hit 69 home runs with a .299 average and 137 OPS+. He gave the Sox a slugger but at a serious cost.

Martínez appeared in just 10 games for the White Sox in 1977 before moving on to the Cardinals, where he found quite a bit more success. His career in Chicago saw him post a 5.57 ERA in 21 innings, walking 12 batters while striking out just 10.

Zisk also wound up playing just a single season for the White Sox, and while he did well, giving up someone of Gossage's stature for just one year of Zisk is a tough one.

Gossage, of course, went on to become one of the more dominant closers this game has ever seen. He played 22 years in the big leagues and was eventually voted into the Hall of Fame. Losing him, especially for just one year of Zisk, is still a tough pill to swallow.

No. 2: Marcus Semien, Chris Bassitt, Rangel Ravelo and Josh Phegley to the Oakland Athletics for Jeff Samardzija and Michael Ynoa - December 2014

Samardzija, a longtime member of the Chicago Cubs, had only just wrapped up his only season with the A's when he was flipped to the White Sox in exchange for this monster return.

He made a full season of 32 starts in 2015 but had a 4.96 ERA and 79 ERA+ along the way. He led the American League in hits allowed, earned runs and home runs surrendered.

Ynoa stuck around for a bit longer, functioning as an oft-used middle relief option for the Sox in 2016 and 2017. In 45 games and 59 innings, he posted a 4.42 ERA and 95 ERA+ with 53 strikeouts and 39 walks.

Ravelo never amounted to anything for Oakland and is currently a member of the San Diego Padres organization on a minor-league contract.

Phegley spent parts of five years with the A's, primarily functioning as the team's backup catcher. He never had much of a bat but was known as a strong defender for the club.

Bassitt and Semien represent the two biggest losses here for the White Sox. The 2021 All-Star made 100 appearances with Oakland over six years, posting a 3.44 ERA and 121 ERA+ across 526 innings. He spent last season with the Mets and continued to improve across the board.

Now, he is expected to shore up the middle of the Toronto Blue Jays rotation in the next few seasons after signing a three-year deal north of the border.

Then there's Semien, who made himself into one of the best power-hitting second basemen in baseball history. He also made the All-Star Game in 2021 and hit 45 home runs that year, the single-season record amongst second basemen.

Since he left Chicago, he has hit 178 home runs and driven in 530 with a 110 OPS+. He would be a much better option at the position than Leury García, Josh Harrison or Elvis Andrus have been over the years.

No. 1: Fernando Tatis Jr. and Erik Johnson to the San Diego Padres for James Shields - June 2016

As if there could possibly be another entrant to top this list.

Shields, the longtime ace of the Tampa Bay Rays and Kansas City Royals, was in the middle of his second season as a San Diego Padre before this beast of a trade went down. He had been struggling to start the 2016 season, so the White Sox's interest here was curious from the start.

In a White Sox uniform, the player formally known as "Big Game James" made 77 appearances with a 16-35 record and a combined 5.31 ERA. His 79 ERA+ was well below average and he saw his strikeouts go down, home runs go up, and walks go up as well. He was awful in every way for a team that was just as awful.

Johnson, a starting pitcher himself, never amounted to much at the major league level. He made appearances for both the White Sox and Padres in parts of four years with a combined 5.28 ERA and 76 ERA+.

Then there's Tatis, one of the top young players in the league. Unfortunately for all fans of the game, he has struggled with injuries (that were his own doing off the field) and he's missed significant time in each of the past four years, including the entirety of the 2022 campaign.

When he's on, Tatis is at or near the top of the league in overall production. In 2021, his only full season, he hit a league-leading 42 home runs with 97 RBI, 25 stolen bases, a .282 average, and an OPS+ of 166. He finished third in the NL MVP voting that year but he will surely earn multiple trophies down the line.

While some may say that Tatis' 14-year contract extension is already an albatross for the Padres, it feels too early to slap that label on it. If he can get healthy and stop getting into accidents off the field, he has a very real shot at a Hall of Fame career. Even if he never played another game at the big league level, his production would outmatch Shields' in a White Sox uniform.