Ranking the best Chicago White Sox winter meetings transactions since 2000

There was a time when the White Sox added noteworthy players at the winter meetings.

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This might be one of the most uneventful winter meetings for the Chicago White Sox in recent history.

Manager Chris Getz communicated that the organization won’t be big spenders this offseason before the season finished, and all signs point to him being a man of his word. In November, the Sox signed several players to contracts worth less than $5 million combined.

The Sox continued their budget-signing streak this month by signing Cal Mitchell and Nick Maton to minor league contracts. Aside from an impending Garrett Crochet trade that is bound to alter the Sox farm system and future in the next few years, Chicago won’t be making a splash in the free-agent market any time soon.

Until then, it’s time to reminisce on the times when the Sox were ambitious and not restricted by a frugal budget and strict rebuild agenda. Here are the rankings for the biggest moves the Sox made during past winter meetings.

4. Yoán Moncada

At the time, trading Moncada spelled nothing but optimism. Moncada came to the Sox in the blockbuster 2016 trade that sent Chris Sale to the Red Sox. In 2016, Moncada slashed .294/.407/.511 between Boston’s High-A and Double-A teams, earning the No. 2 overall prospect ranking entering the 2017 season.

He became the No. 1 overall prospect months later. Moncada’s quick hands, speed, and build made him a naturally gifted player.

Though it took a few years, Moncada finally broke out in 2019 with the Sox. His slash line through 132 games was .315/.367/.548, and he tacked on 25 strikeouts. He ranked third in the league in batting average, tenth in offensive WAR, tenth in OPS, and first in putouts and double plays by third basemen.

Until he became susceptible to injuries, it looked like the Sox wrote their hot-corner ticket for years to come.

3. Lance Lynn

Trading for Lynn in 2020 was one of the best tactical moves former general manager Rick Hahn made.

At the time, the Sox lacked star power in the back half of their starting rotation. Lucas Giolito and Dallas Keuchel packed a mean one-two punch, but with Lynn in the mix alongside a budding Dylan Cease, the Sox seemed like an even bigger threat after making the wild card that year.

While parting with Dane Dunning wasn’t easy, acquiring Lynn from the Rangers after two consecutive years of being nominated for the Cy Young Award was worth the cost.

Lynn had a phenomenal season with a 2.69 ERA, a 1.07 WHIP, and a 10.1 K/9 rate. He was named an All-Star in 2021 and placed third for the Cy Young Award.

His reputation for getting under opponents’ skin with his relentless fastball-dominated pitch arsenal and smack talk mixed well with Tim Anderson’s attitude and Liam Hendriks’ winning mentality, making 2021 one of the most memorable seasons for the Sox since 2005.

2. Lucas Giolito

Acquiring Giolito from the Nationals in 2016 was another pivotal move that, paired with the Chris Sale trade, kicked off Chicago’s mini rebuild.

Adam Eaton was among the AL MVP candidates that year but his talent only went so far on the Sox. Giolito was the 12th-best prospect in baseball and rapidly rose through Single, Double, and Triple-A in Boston’s farm system, which combined for a 2.97 ERA and 116 strikeouts in 22 games. He established himself as a dominant pitcher before and after Tommy John surgery in 2014.

Chicago relied on Giolito’s excellent pitching from 2017-2022, during which he had a 4.11 ERA, five complete games, and three shutouts.

He was named an All-Star in 2019 and was a Cy Young candidate for three consecutive years. The Sox built their rotation around Giolito, which started with trading the Cubs for Dylan Cease in the same transaction that brought Eloy Jiménez to the Southside in 2017.

They later signed Dallas Keuchel in 2020 and held onto Carlos Rodón’s potential. Without Giolito, the Sox probably wouldn’t have gone on their short-lived playoff run in 2020 and 2021. 

1. Scott Posednik

Ranking Posednik anywhere but first place would be a mistake.

The Sox restructured their lineup during the 2004-2005 offseason after finishing second to the Twins in the AL Central, and trading for Posednikk was the first of several moves geared toward this effort. Posednik’s addition brought diversity to a righty-heavy lineup, upgraded the Sox’s base stealing, and freed up money to sign Tadahito Iguchi.

Bringing Posednik in was the first of several strategic moves that made the Sox World Series champions.

Posednik became a pivotal player on the team. He finished the season with a .290 batting average and 59 stolen bases. In the postseason, he was even better. He batted .286 and slugged .551 in 12 playoff games.

His memorable walk-off home run in game 2 of the ALDS against the 2004 World Series champions will forever be remembered. Without Posednik, the Sox wouldn’t have ended their 88-year World Series drought.

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