Former Chicago White Sox starting pitcher Dylan Cease has 210 million reasons to be thankful this Thanksgiving.

On the eve of the classic American holiday, Cease agreed to a massive contract with baseball’s only Canadian franchise. The reigning AL champion Toronto Blue Jays gave him a seven-year, $210 million deal to help anchor a rotation built for a World Series return.

Toronto’s 2026 rotation now projects as Kevin Gausman, Dylan Cease, Trey Yesavage, José Berríos, and Shane Bieber. Five right-handers. Five All-Star-caliber arms. 

Cease joined the White Sox organization back in 2017 as one of the prized pieces in the José Quintana deal with the Cubs. He grew slowly but steadily, eventually blossoming into one of the most dominant starters in the American League. Somehow he was never selected to an All-Star Game, but he famously finished as the runner-up for the 2022 Cy Young with a 14–8 record, 2.20 ERA, and 227 strikeouts — still the high-water mark of his career.

One of Cease’s greatest strengths has always been his durability: 32 or more starts every season from 2021–2025, and 12 starts during the COVID-shortened 2020 campaign.

So now that Cease is cashing in after two seasons in San Diego, this feels like the perfect moment to revisit the trade that sent him to the Padres — and to grade it from a White Sox perspective.

Trade Details

Padres receive: RHP Dylan Cease

White Sox receive: RHP Drew Thorpe (MLB Pipeline No. 85; SD No. 5) OF Samuel Zavala (SD No. 7) RHP Jairo Iriarte (SD No. 8) RHP Steven Wilson

At the time, it was a respectable haul. Three Top-10 prospects from the Padres’ system, a controllable MLB reliever, and a Top-100 arm in Drew Thorpe that looked nearly MLB-ready.

The early returns were encouraging.

Steven Wilson had a down year in Chicago’s bullpen, and teenager Samuel Zavala looked overmatched as a 19-year-old in High-A. But Drew Thorpe and Jairo Iriarte flashed real promise.

Thorpe dominated Double-A, going 7–1 with a 1.35 ERA for Birmingham and pushing his minor-league record to an absurd 21–3 with a 2.17 ERA. How could that not excite a White Sox fan?

Iriarte also impressed in Double-A. By the time the 2024 season wrapped up, both pitchers had debuted in the majors.

Iriarte moved to the bullpen and posted a 1.50 ERA in six September outings.

Thorpe held a 3.03 ERA over his first seven MLB appearances before a late-season arm issue led to multiple rough outings — and eventually Tommy John surgery that wiped out his entire 2025 season.

Then came the reversal. In 2025, Wilson was a late-inning weapon, Zavala rediscovered his swing in Winston-Salem and climbed back into the White Sox Top 30, while both Thorpe and Iriarte were non-factors.

Where The Return Stands Today

Just last week, Steven Wilson was moved to Tampa Bay in the trade that brought Everson Pereira and Tanner Murray to Chicago.

Samuel Zavala enters 2026 ranked No. 28 in the Sox system. He’s still young and talented, but hasn’t quite put everything together.

Jairo Iriarte is likely to open 2026 in Triple-A. The Sox hope a few mechanical tweaks can help him rediscover the stuff he showed in 2024. With a strong start, he could earn MLB innings again, but it's hard to ignore the ugly 2025 figures (7.24 ERA in 46 Triple-A innings).

Drew Thorpe is the wild card — and the key to the trade. He should compete for a rotation spot in 2026, but he may not be ready to go by Opening Day. Still, if he returns healthy, he has mid-rotation upside with a chance to be even more.

Meanwhile, Cease went 22–23 with a 3.98 ERA and 11.1 K/9 across his two seasons in San Diego. And as expected, he never negotiated an extension after hiring Scott Boras. He played it out, hit free agency, and cashed in for $210 million — with the Padres receiving nothing more than a compensatory fourth-round pick (due to the qualifying offer) on the way out.

Was This Trade Bad for the White Sox?

Honestly, no. And here’s why.

The writing was on the wall from the moment Cease hired Boras to represent him. Boras is the best in the business. He gets his clients the most money, and he rarely lets them settle for discount extensions — not when $200 million is out there on the open market.

The White Sox have never given out a contract worth even $100 million. There was no realistic path to Cease staying long-term.

That means the Sox had two choices: (1) trade him with two years of control, or (2) lose him for nothing after two seasons with a losing record.

They took the only logical route.

Did they nail the return? Not yet. I’m not particularly optimistic that Irairte or Zavala will ever be meaningful contributors to the White Sox. Wilson is already gone. But the entire success of this trade will hinge on whether Drew Thorpe becomes a legitimate starter once he’s fully healthy.

And I’m still bullish on him. 

Thorpe’s absence in 2025 made it easy for fans to forget how good he looked in 2024. His command, his feel to pitch, his minor-league dominance — those things usually translate. If he becomes a long-term rotation fixture, that alone could be as valuable as what Cease would’ve given them in 2024–2025.

Final Grade: C

This isn’t a trade to celebrate. But it’s not a failure either — not yet. Until we know what the Sox get from Drew Thorpe in 2026, the book isn’t closed.