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Diam⚾️ndBuzz: MARCH 6, 2025

WHITE SOX: A LOOK AT A DYNASTY THAT NEVER WAs

It is often said that baseball is a game of patience, of tradition, and of long-term vision. But when we examine the history of the Chicago White Sox over the past decade, one thing becomes painfully clear—patience was abandoned, tradition was discarded, and long-term vision was utterly absent.

The White Sox, a franchise rich in history, have seen their share of missteps. But few, if any, can match the sequence of trades that saw three Cy Young-caliber pitchers—Chris Sale, Dylan Cease, and Garrett Crochet—shipped away for what ultimately amounted to nothing. Add in the departure of a reliable workhorse like José Quintana, and what might have been a historic rotation has instead given way to the worst season in Major League Baseball history.

Let’s examine how, through a series of ill-advised moves, the White Sox dismantled what could have been an all-time great pitching staff, and how ownership’s decisions doomed the franchise to futility.

THE CHRIS SALE TRADE: A FOUNDATION DESTROYED

Chris Sale, in 2024, became what many of us had long expected—a Cy Young Award winner. His dominance with the Atlanta Braves was no accident; it was the culmination of years of elite ability, the same ability the White Sox once had in their possession.

In 2016, Sale was traded to the Boston Red Sox for a package headlined by Yoán Moncada and Michael Kopech. At the time, it was a deal framed as a necessary step toward a rebuild. But as we look back, it is evident that the return never materialized in a meaningful way. Moncada, despite flashes of promise, has been inconsistent, plagued by injuries and underwhelming production. Kopech, once touted as the next great flamethrower, has struggled with control issues and has yet to establish himself as a reliable starter.

Meanwhile, Sale continued his march toward Cooperstown, adding a World Series title and, finally, in 2024, a Cy Young Award. Had he remained in Chicago, he would have been the White Sox’s anchor, the pitcher around whom a dominant rotation could have been built. Instead, the Sox were left with little to show for one of the best left-handed arms of his generation.

DYLAN CEASE: A TRADE THAT MADE NO SENSE

The story of Dylan Cease is not merely one of talent lost, but of timing miscalculated. Cease, a Cy Young finalist in 2024, was traded to the San Diego Padres in 2023 in a move that, even at the time, seemed premature.

The return? A collection of prospects—Drew Thorpe, Jairo Iriarte, and Samuel Zavala—none of whom have made an impact at the Major League level. It was a transaction that underscored a fundamental misunderstanding of value; instead of building around a proven commodity, the White Sox opted for uncertainty.

Cease’s ascension in San Diego has been a testament to what the White Sox once had: a power pitcher with elite movement and command. His dominance in 2024 left Chicagoans wondering what could have been if he and Sale had been paired at the top of the rotation, a one-two punch that could have carried the team deep into October.

GARRETT CROCHET: ANOTHER ARM, ANOTHER MISTAKE

Perhaps the most frustrating of all is the case of Garrett Crochet. Drafted by the White Sox in 2020, Crochet was envisioned as a cornerstone of the team’s future. And yet, in 2023, he too was dealt away, this time to the Boston Red Sox, for what was supposed to be bullpen help and an offensive prospect.

What happened next was all too familiar: Crochet flourished, finishing fifth in the Cy Young voting in 2024, while the players Chicago acquired in return failed to make any lasting impact. It was another instance of the White Sox undervaluing their own talent, dealing away elite arms for marginal returns.

JOSÉ QUINTANA: A STABILIZING FORCE NEVER FULLY APPRECIATED

José Quintana’s career is one defined by consistency. Though never the ace that Sale or Cease became, he was a reliable innings-eater, a left-hander who provided stability every fifth day. The White Sox, however, saw him as expendable, trading him to the Chicago Cubs in 2017. The irony? The primary piece they received in return was Dylan Cease—whom they later traded away.

Had the White Sox simply kept Quintana from the beginning, they would have had a solid mid-rotation presence, reducing the need to frantically cycle through stopgap arms over the years.

THE ROTATION THAT NEVER WAS

What if these moves had never happened? What if patience had prevailed? The answer is almost unfathomable for White Sox fans. Consider this potential rotation in 2024:

Chris Sale – The Cy Young winner and veteran ace

Dylan Cease – A dominant No. 2, capable of overpowering any lineup

Garrett Crochet – A left-handed force, finishing in the top five for Cy Young honors

José Quintana – A reliable veteran presence

An open spot for developing talent or additional acquisitions

This is the type of rotation that changes the trajectory of a franchise. This is the type of rotation that wins championships. And yet, instead, the White Sox finished with the worst record in Major League Baseball history.

OWNERSHIP’S ROLE IN AVOIDABLE FAILURE

The responsibility for this collapse does not lie with any one general manager or scouting director. It extends to the very top of the organization. Jerry Reinsdorf and his front office have overseen an era of mismanagement, a series of decisions that have left the White Sox without an identity, without direction, and without the pitching talent that once defined them.

Great organizations understand value. They recognize when to trade, when to build, and when to commit to a core. The White Sox, however, have consistently miscalculated, choosing to dismantle rather than develop. And the results speak for themselves.

WHERE DO THEY GO FROM HERE?

The lesson must be learned. The White Sox must embrace a new philosophy—one that values patience, stability, and long-term vision. They must stop trading away elite pitching talent for the allure of “prospects” that rarely pan out. They must recognize that rebuilding does not mean tearing everything down—it means making wise decisions that preserve and enhance a franchise’s strengths.

The White Sox had, at one point, assembled one of the most formidable collections of pitching talent in baseball. And yet, they let it slip away. Now, as they stand at the bottom of the standings, they must ask themselves: Was it worth it?

For the fans who have endured season after season of disappointment, the answer is all too clear. It was not.

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