Dylan Cease might check all the boxes for the Chicago Cubs this winter.
His agent, Scott Boras, agrees.
Jed Hoyer has already said the Cubs’ top priority this winter is pitching.
That’s evident given the team ran out of quality starting pitching options in the postseason due to injuries and ineffectiveness. And since the season ended, the Cubs lost a slew of veteran relievers plus starter Shota Imanaga (who may still return to the team if he accepts the qualifying offer).
[Could Cody Bellinger-Cubs reunion make sense?]
Cease is a free agent and could help fill a void for the Cubs — the team that originally drafted him out of high school in the sixth round in 2014. Hoyer and Theo Epstein traded Cease away back in July 2017 in the Crosstown swap that brought José Quintana to the North Side and sent Cease and Eloy Jiménez to the White Sox.
Boras spoke about the potential reunion between Cease and the Cubs in an exclusive interview with Marquee Sports Network contributor Bruce Levine at the GM Meetings in Las Vegas on Wednesday:
“Well, I think we all know how Dylan Cease pitches in Wrigley Field,” Boras said. “He is dominant. And to have durability, to have dominance — he has got both. Other than [Tarik] Skubal next year, I don’t see a pitcher in the market coming that is going to have the potential that Cease has, and the proven element of durability to go along with that quality and potential. Two hundred strikeouts a year, it’s just not something the game has.”
[Catch the full exclusive interview with Scott Boras]
Cease certainly racks up the whiffs. He has tallied at least 200 strikeouts in each of the last five seasons, leading MLB in strikeouts per nine innings in the 2021 and 2025 campaigns.
He has not missed a start during that time, either, pitching in at least 32 games every year for the White Sox and San Diego Padres.
That type of skillset would fit perfectly on the Cubs, who had a strong starting staff but missing bats was a clear weakness for the group. The Cubs rotation ranked 27th in MLB in strikeouts per nine innings in 2025 (7.53) and their 20.5% strikeout rate was 23rd in baseball.
Despite all the whiffs, Cease has had up-and-down performance over the last few years.
His ERA, WHIP and WAR per season is as follows:
2022: 2.20 ERA, 1.11 WHIP, 6.4 WAR
2023: 4.58, 1.42, 2.2
2024: 3.47, 1.07, 4.1
2025: 4.55, 1.33, 1.1
By that pattern, it may mean he’s due for an elite season in 2026…
But in all seriousness, Cease could be one of the Cubs’ top targets this winter. Even with the uneven performance, imagine how the rotation would have looked with Cease in it during the 2025 playoffs.
Instead, the Cubs had to face the dynamic righty with the Padres during Game 2 of the NL Wild-Card round. He shut out the North Siders in 3.2 innings, striking out five.
[MORE: What Cubs make of Shota Imanaga relationship after offseason moves]
Cease has only pitched three other games at Wrigley Field besides that postseason contest, going 2-1 with a 2.50 ERA and 27 strikeouts in 18 innings.
“Everybody knows that when you go into the playoffs, you want a No. 1,” Boras said. “Why? You got a five-game series, you want them to throw twice. You want to have that chance. You want to have your most dominant arm out there.
“That’s why the Dodgers signed Blake Snell. And so those teams that are doing that are winning championships, and I think getting those types of arms really, really increase your opportunity to achieve that.”
Cease will turn 30 in December and as a free agent for the first time, this is his best chance to secure a megadeal.
With some question marks attached, what will his contract ultimately look like? And will the Cubs be shopping at the top end of the free agent pitching market?
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