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Revisiting the 3 most significant trades from the White Sox rebuild

Who won the biggest trades the White Sox made during the previous rebuild?

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As the White Sox near an inevitable retooling of their roster at the Aug. 1 trade deadline, let's look back at how they got here.

Since 2016, the front office has been building the White Sox roster as we know it today. They made pivotal trades along the way, flipping invaluable veteran players for emerging, promising prospects.

Who won those trades?

Let's break down three of the most significant trades the White Sox made and see where the jury stands on all of them.

The Adam Eaton trade

White Sox trade: Adam Eaton to the Washington Nationals

White Sox receive: Lucas Giolito, Reynaldo Lopez, Dane Dunning

At this time, in 2016, Eaton was a valuable two-way player. He hit .284 with an OPS just under .800. He led the league in triples and knocked 14 balls out of the park with 59 RBIs. His defensive services in the outfield were helpful, too.

Eaton helped the Nationals to a World Series in 2019. He hit two home runs and knocked in six batters in that series, hitting .320 with an OPS of just under 1.000 points. Though, he struggled to stay on the field for most of his four-year tenure, playing over 100 games in just one season.

The White Sox got an ace and a reliable bullpen arm in return for Eaton. They also flipped Dunning into Lance Lynn years later, adding an All-Star starter to their rotation in 2021.

For what it's worth, they signed Eaton back to the team in 2021. He wasn't all that great, hitting .201 in 58 games. But it came full circle for the Sox in the end.

Verdict? Sox win.

Eaton played a role with the Nationals and helped them to a championship, but the Sox got multiple key pieces to their roster. Did it help them ultimately in the long run? Maybe not, considering all the names in that trade are rumored on the trade block, as of this writing. But I'll take the White Sox in this one, considering the haul they got back.

"Huge win," Frank Thomas said of the Eaton trade on the White Sox Pregame Live show. "White Sox definitely won that trade."

Trading their Ace

White Sox trade: Chris Sale

White Sox receive: Yoan Moncada, Michael Kopech, Luis Alexander Basabe, Victor Diaz

The White Sox drafted one of the game's best in 2010 when they selected Sale with the No. 13 pick in the draft. He jumped up to the majors immediately, debuting that same season at 21 years old.

By 2012, he was a full-time starter with the Sox, quickly racking up accolades. He earned five straight All-Star nods with the Sox and finished top-5 in AL Cy Young voting four times.

To give them that extra boost in the farm, the Sox traded for Moncada --- MLB.com's second-best prospect at the time --- and Kopech, the No. 16 ranked prospect. Moncada strung together an electric 2019 season, but he hasn't been the same from the plate since. Kopech has endured growing pains ever since leaving the bullpen in 2022.

Verdict? Red Sox win.

The trade made a lot of sense for the White Sox at the time. And while Sale only played 11 games between 2021 and 2022, he helped them win a World Series in 2018. Both Kopech and Moncada earned pivotal roles with the South Side, but haven't lived up to them at this point.

Crosstown trade

White Sox trade: Jose Quintana

White Sox receive: Dylan Cease, Eloy Jimenez, Matt Rose, Bryant Flete

After winning the World Series in 2016, Theo Epstein and the Cubs hoped to add a valuable arm to their rotation to make another push post-2016. In 2017, they handed the White Sox some of their best prospects for the lefty starter, Quintana.

Jimenez --- the No. 14 prospect in 2017 --- and Cease, No. 77, were sent to the South Side before seeing the majors. Both quickly propelled through the minor leagues and made their respective debuts in 2019.

Jimenez's rookie season was astounding. He played 122 games and hit 31 home runs with 79 RBIs. Cease quickly became a backend starter and made an indelible mark last season, holding a 2.20 ERA and earning runner-up honors for the AL Cy Young Award.

Quintana was never quite the same pitcher with the Cubs. He couldn't get his ERA under 4.00 and missed virtually the entire shortened 2020 season due to injuries. The Cubs lost the NLCS and the NL Wild Card in 2017 and 2018, respectively.

Verdict? South Side wins.

The White Sox sold on Quintana at the right time, earning two key roster pieces in return. Cease is entering the prime of his career and one could make the argument Jimenez hasn't yet reached his ceiling.

Assuming Cease and Jimenez are part of the few who are protected from trade over the next two weeks, I would mark this as a win for the White Sox.

"If the Cubs, today, have a Cease and a Jimenez on the field, they would be a different ball club right now," Ozzie Guillen said on the White Sox Pregame Live show. "They might be in the pennant race."

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