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10 memorable White Sox trades from the Winter Meetings

by Jordan Lazowski

The Winter Meetings are usually a few days packed with a lot of action around baseball – both signings and trades with a pretty large magnitude have become the norm at these meetings. Jacob deGrom’s signing with the Rangers on Friday night served as the sort of sneak preview of what could come over the next few days for some teams in the market for big prizes.

The White Sox, however, have not been strangers to making bigger moves to improve the team – or shape it differently – during these days when all general managers and high-profile agents are around. With the Winter Meetings once again beginning on Sunday, here are 10 memorable trades the White Sox have made during the meetings, the aftermath of each of the moves, and a review of who won each trade with the benefit of hindsight.

December 8, 2020: White Sox acquire Lance Lynn from the Texas Rangers in exchange for Dane Dunning and Avery Weems

We start with the most recent major Winter Meetings move. The White Sox, fresh off their first playoff season since 2008, were ready to bolster their team under *ahem* new manager Tony La Russa. In an offseason that would also include the signings of Adam Eaton and Liam Hendriks, Lynn was coming off two straight Cy Young-caliber seasons in Texas on a team that was looking to rebuild. The trade gave the Rangers a potential future building block while the White Sox will be entering their third season with Lance Lynn after signing him to a two-year extension back in 2021.

Winner: White Sox. At least for now. Weems posted a 5.14 ERA as a 25-year-old in AA last season, and Dane Dunning still hasn’t shown more than a back-end-of-the-rotation-type starter potential. Meanwhile, Lynn has been the top-of-the-rotation ace the White Sox were hoping for when they traded for him. It was a great move at the time in selling high on Dane Dunning, and it remains a great move today.

December 11, 2018: White Sox acquire Ivan Nova from the Pittsburgh Pirates in exchange for Yordi Rosario and $500,000 in international signing pool space

In the midst of a rebuild, the 2019 White Sox needed someone who could eat innings. Enter Ivan Nova, who was too expensive for a rebuilding Pirates team that just wanted to open up opportunities for other players. Truthfully, as a team that has Nova, Gerrit Cole, and Jameson Taillon, it’s fair to feel this era of the Pirates underachieved. Nova, however, did his part in three seasons with the team, posting a 3.99 ERA and 103 ERA+ in 412.2 innings as a steady starter in the middle of their rotation.

Winner: White Sox, barely. This one really could be considered a “no one won this one” deal. Nova was exactly as advertised with the White Sox, posting 187 innings on a team that desperately needed them, which gives them the edge. However, he also pitched for a team that had no expectations and went nowhere at the end of the season. Yordi Rosario never made it to the big leagues, and it’s unclear what the Pirates did with the $500K in cap space – none of their prospects from that signing period have really shown out. So, White Sox by default.

December 6, 2016: White Sox acquire Yoan Moncada, Michael Kopech, Luis Basabe, and Victor Diaz from the Boston Red Sox in exchange for Chris Sale

In the first of two major moves the White Sox made at the Winter Meetings, it feels like we all remember where we were when the team finally committed to a rebuild. It was the most divisive move the White Sox had made in a long time when it came to fan reactions, however, it also signaled a clear direction for a team that just wasn’t going to achieve the way it had been previously built.

“It’s never easy to trade a pitcher the caliber of Chris Sale,” said Rick Hahn at the time. “We have made no secret heading into the offseason our goal is to put ourselves in the best position to contend for an extended period of time for multiple championships. Given where we were as an organization entering this offseason, we knew we were going to have to make some painful decisions.”

Winner: Red Sox. Flags fly forever, and Sale was an integral part of the club’s 2018 World Series Championship. Sale has hardly been the same since due to injury, helping to ease some of the pain of this sort of deal, but it doesn’t make up for the fact that the White Sox wasted the time they had with Sale and have yet to capitalize on the prospect capital they received in return.

December 7, 2016: White Sox acquire Lucas Giolito, Dane Dunning, and Reynaldo Lopez from the Washington Nationals in exchange for Adam Eaton.

If you thought the White Sox were done at the Winter Meetings with the Sale trade, you would’ve been incorrect. Just one day later, the White Sox sent Adam Eaton over to the Nationals in what continues to be a pretty big package – one that had Nationals fans scratching their heads at the time. Eaton was coming off a 6.6 fWAR season with the White Sox and had plenty of team control, so it was fair for the White Sox to command a lot of value. The White Sox, on the other hand, stocked their farm system with arms in a way that they hadn’t in previous seasons.

Winner: Toss-up. In order to be consistent with “flags fly forever” from the Sale trade, credit where it’s due with Eaton becoming a part of the 2019 World Champion Washington Nationals (.279/.365/.428, 2.3 fWAR). However, that would be his best season in Washington and also his healthiest, so it was far from the value the Nationals expected to get when they traded for Eaton. In fact, his 4.6 fWAR in his time with the Nationals didn’t even add up to his single-best season with the White Sox (6.6 fWAR in 2016). Giolito has become a Cy Young candidate, Reynaldo Lopez a key piece of the White Sox bullpen, and Dunning turned into another key piece of the rotation in Lynn. Even without a championship, these three have done plenty individually to move this trade back into the “toss-up” category – compared to the inconsistent careers of Moncada and Kopech to this point.

December 9, 2015: White Sox acquire Brett Lawrie from the Oakland Athletics in exchange for J.B. Wendelken and Zachary Erwin

This was quite the offseason for the White Sox – it involved trading for Todd Frazier, but also signing Dioner Navarro and Alex Avila, so it was a split offseason, to say the least. However, they had one more move up their sleeve, trading for Brett Lawrie from the Oakland Athletics to help shore up a middle infield that was in desperate need of some talent (Tim Anderson would not join the team immediately, remember). With Lawrie, the White Sox were supposed to be getting a fiery character for two seasons to help a team that was still intent on winning. They didn’t get what they hoped from him – nor did they win.

Winner: Athletics, barely. Lawrie was only able to play 94 games for the White Sox in what would become his final major league season, hitting .248/.310/.413 and posting a 1.1 fWAR. Erwin is still in the game today, but is 28 years old and has never pitched above AAA. Wendelken, believe it or not, is who moves this trade slightly in favor of Oakland, posting a 3.62 ERA and 117 ERA+ in 112 innings with the Athletics before being traded to Arizona in 2021. This wasn’t a massive trade by any means, and it’s not like the Athletics ran away with a steal of a trade, but the Athletics got the most production out of the two players who spent time in the majors. This is all with the benefit of hindsight of course.

December 9, 2014: White Sox acquire Jeff Samardzija and Michael Ynoa from the Oakland Athletics in exchange for Marcus Semien, Chris Bassitt, Josh Phegley, Rangel Ravelo

This was a loaded offseason for the White Sox that included the signings of David Robertson and Melky Cabrera to go along with their new top-of-rotation starter in Samardzija. The former Notre Dame two-sport athlete was coming off an all-star season with the Cubs and Athletics, posting a 2.99 ERA in 219.2 innings. However, this would be far from the Samardzjia that turned up on the South Side – the right-hander posted a 4.96 ERA in 214 innings on a team that immensely underachieved for the amount of money that was put into the team. However, take a look at that roster – the holes were evident.

Winner: Athletics. A lot of patience paid off for the Athletics in this trade, as both Semien and Bassitt turned into pretty high-quality players, to say the least. This trade definitely wasn’t supposed to look this lopsided at the time, and while this may end up being one of Rick Hahn’s worst trades, not many fans really saw it that way when the trade was first announced. Still, Samardzija was not good in his only season in Chicago, and while it took Semien some time, he turned into a huge second baseman. Bassitt, on the other hand, has been an awesome starter that fans have hoped the White Sox would either sign/trade for in recent years.

December 6, 2011: White Sox acquire Nestor Molina from the Toronto Blue Jays in exchange for Nestor Molina

Kenny Williams was never a big fan of saying the word “rebuild” – but, with this trade, he said it for what seemed to be the first and only time as a general manager.

“It is the start of a rebuilding,” Williams said. “You guys know I have not used that word in 12 years. It’s the start of a rebuilding now. Is it the start of a falling-domino-type rebuilding? No. Absolutely not. Because as we currently sit, I do not like what is currently being offered for any of our valuable veteran pieces. I’m of the mindset that while we may do a couple of more things, as we sit right now we’ll probably keep the rest of the pitching intact and we’ll focus on some peripheral things to kind of continue to get a piece here or there that will help us in 2013, 2014. But as I sit here right now I don’t see any deals for any of the other pitchers.”

So, Williams, in typical fashion, did not commit to a full-scale rebuild like the one the team undertook a half-decade later, but he did move his young closer Sergio Santos after two successful seasons on the South Side – he posted a 3.29 ERA in 115 innings with the club to go with 30 saves in a 2011 campaign that set him up to be the team’s future closer. The team, instead, would find their next closer in Addison Reed, their third-round draft pick in 2010. Molina was a highly regarded prospect within the Jays’ organization at the time, posting a 2.21 ERA in 130.1 innings for the Blue Jays in High-A and AA in 2011.

Winner: Toss-up. The Blue Jays should technically be considered the “winners” here most because Nestor Molina never made it to the major leagues. Santos, however, would not be the closer in Toronto and would only pitch 51.2 innings across three injury-plagued seasons up North. His 5.23 ERA left a lot to be desired, and he was never able to re-capture what he had with the White Sox. So, it’s hard to say the Blue Jays “won” a trade in which they didn’t get the value they were expecting – or really anything near it. No one really got what they wanted here.

December 3, 2007: White Sox acquire Carlos Quentin from the Arizona Diamondbacks in exchange for Chris Carter

This was a pretty busy offseason for the White Sox after a brutal 2007 campaign. The club quickly traded Jon Garland for Orlando Cabrera and signed Scott Linebrink to a four-year, $19M contract. The team then went and got Quentin, who had fallen out of favor due to injuries/poor performance in Arizona. Once considered a top prospect, Quentin batted .214 with five home runs and 31 RBIs in 81 games for the NL West champions in 2007. He lost his starting job in right field and was demoted to the minors in July, then recalled a few weeks later. But he missed most of August with a strained right hamstring and was left off the playoff roster.

Chris Carter (yes, that slugger) wouldn’t spend much time with the Diamondbacks; in fact, Carter would never play a game in the Diamondbacks’ organization, being used as one of several players in the trade that brought Dan Haren to Arizona. Quentin, on the other hand, would hit .257/.352/.505 with the White Sox before heading to San Diego for two more stellar seasons. He would play his last season at the age of 31, with injuries limiting what could’ve been for his career.

Winner: White Sox. Because of how well Haren pitched with the Diamondbacks, it moves this trade a bit closer to a toss-up. However, Quentin became just a phenomenal player on the South Side, likely punching his way out of an MVP Award in 2008. Quentin may never have matched his 2008 campaign, but he was a consistently a 20-25 home run hitter that played solid defense as well. This was among the most successful Winter Meetings moves on this list for the White Sox.

2004: White Sox acquire Scott Podsednik, Luis Vizcaino, and a PTBNL (Travis Hinton) from the Milwaukee Brewers in exchange for Carlos Lee

Here’s an interesting throwback to a trade we’re all pretty familiar with. Per MLB.com beat writer Scott Merkin: “There were rumblings of the White Sox interest in Scott Podsednik on the second day of these Winter Meetings in Anaheim. But it wasn’t until the Winter Meetings were coming to a close that this deal was executed. In fact, White Sox executive vice president Ken Williams, who was general manager at the time, spoke of the acquisition at a press conference in front of only a handful of reporters still remaining.”

Following a disappointing 2004 season, the White Sox began to reshape themselves to establish a more balanced team. Out were Carlos Lee and Magglio Ordonez – in were Scott Podsednik, Tadahito Iguchi, Pablo Ozuna, and others. You know the story from here though – the White Sox went on to win the World Series, while Carlos Lee continued to be a force during his time in Milwaukee. It’s a trade that didn’t make sense on the surface but benefitted the White Sox in the long run. Vizcaino was coming off a season in which he had a 3.75 ERA in 72 innings. A man of consistency, he would post a 3.73 ERA in 70 innings with the 2005 White Sox.

Winner: White Sox. Lee was still an All-Star, but both Podsednik and Vizcaino played pivotal roles on the 2005 World Champion roster. It’s a move that the White Sox shouldn’t necessarily have won on paper, and at the same time, Milwaukee didn’t exactly lose this trade either. Giving up a guy with a .891 OPS in exchange for a speedster (70 SB) who couldn’t hit (.677 OPS) should not have worked for the White Sox. But, as we mentioned in the Sale trade: flags fly forever.

December 4, 1957: White Sox acquire Early Wynn and Al Smith from the Cleveland Indians in exchange for Minnie Minoso and Fred Hatfield

Here’s a fun one that I have to credit Scott Merkin for finding in an old Winter Meetings article he once wrote! This one was definitely a shocker for the White Sox, deciding to trade an All-Star and MVP candidate in Minoso. Hatfield ended up being just a throw-in for this deal, coming off his age-32 season in which he posted just a .544 OPS. Wynn was heading into his age-38 season and had a 4.31 ERA in 1957, but had posted three straight All-Star campaigns. Al Smith was 30 at the time, but had an MVP-caliber season just two years prior and looked to still have plenty to contribute. Wynn and Minoso, obviously, were the two big swaps here at the end of the day.

Winner: White Sox. Wynn would go on to revitalize his career a bit with the White Sox – which is odd to say about someone who pitched with the team in his age 38-42 seasons. Wynn would win the 1959 Cy Young and would be a critical part of the White Sox’ World Series run that year. Similarly, Al Smith was a big part of that club, and in his tenure with the White Sox, would post a .789 OPS. The team also wouldn’t be without Minoso for long, as they re-acquired him just a few years later. Minoso would remain a model of consistency in his two seasons with Cleveland, but they wouldn’t get nearly as close to a World Series Championship as the White Sox did.

Honorable Mentions

  • 1961: White Sox acquire Eddie Fisher, Dom Zanni, and Bob Farley from the San Francisco Giants in exchange for Billy Pierce and Don Larsen
  • 1984: White Sox acquire Ozzie Guillen from the San Diego Padres in exchange for LaMarr Hoyt, Kevin Kristan, and Todd Simmons
  • 1994: White Sox acquire Keith Heberling and a PTBNL (Lyle Mouton) from the New York Yankees in exchange for Jack McDowell

With a vast history that goes well beyond the 13 trades mentioned in this article, the White Sox have been no strangers to making moves at the Winter Meetings. With still so many needs for the 2023 version of this team, the White Sox would likely benefit from some extended time with other GMs to get some work done this week. With a Winter Meetings that is expected to be pretty active, hopefully, the White Sox can find themselves partaking in some of that activity.

What were some of your favorite Winter Meetings deals? Let us know in the comments!

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Jim David

Two far too costly go for broke trades

Norm Cash, John Romano and Bubba Phillips to Cleveland for Minoso and three fringe players Dick Brown, Don Ferrarese and Jake Striker

Earl Battey and Don Mincher to Washington for 1B Sievers

Jim David

Those hung with me all these years as the worst ones possible. They had always been th gutless wonders and all of a sudden they had nice promising kids coming up. Another horrid trade that same post 59 season was the giveaway of GG RF Johnny Callison for clank 3B Gene Freese. Sox might have gone to 3-4 WS with their great 60s pitching with that offense.

Jim David

(The reply should have said HITLESS Wonders, not gutless ones)!!

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