You know, I would love to believe these rumors, buy in to the hype and be as optimistic of a fan as possible, but I’ve also witnessed how the Chicago Cubs have operated in free agency under Jed Hoyer and the Ricketts. So yeah, the rumors might be growing, but it doesn’t make them any more true.
But hey, I won’t deny you or any other fan any feelings of excitement over the possibility that the Cubs do end up making a serious pursuit of free agent starting pitcher Dylan Cease. Chicago baseball insider Bruce Levine already linked the Cubs to Cease and now USA Today’s Bob Nightengale has some additional intel from industry sources, who forecast a huge addition to the Cubs’ starting rotation.
On Monday, Nightengale called the Cubs the biggest sleepers of the offseason and relayed the following whispers coming from front office executives.
Via USA Today.
The Chicago Cubs know that finishing second to the Milwaukee Brewers in the NL Central every year is inexcusable, and with Tucker expected to depart for greater riches, they’ll have plenty of money to burn. They want another corner outfielder, and will be shopping in the expensive aisle for starting pitching, with fellow GMs predicting they could land Framber Valdez and/or Dylan Cease.
Hey, that would be great, however they are not signing Cease AND Framber Valdez. That kind of puts the whole prediction further into question, but it’s kind of obvious why other GMs think the Cubs would be in this market.
I mean, the Cubs should be spending on top free agents and they have the need in the starting rotation. Cease seems like a perfect fit to add to the current rotation and given some of the success by the pitching staff for the Cubs, you’d be led to believe that Cease could elevate his game after a down 2025 season.
But the big question is will the Cubs actually go out and pursue Cease, who is projected to land a deal that guarantees him about $30 million annually over five years at the minimum. The Cubs have not signed a pitcher to a contract worth more than $100 million since 2018, when Theo Epstein signed Yu Darvish to a six-year, $120 million deal.
Meanwhile, if you prefer Valdez as a Cubs target in free agency, he’s also projected to sign a deal between $150 million and $200 million this offseason.
I wish I had more confidence in the team actually giving it a shot with these type of free agents, but seeing the track record by Hoyer, it’s unlikely unless something dramatically changes in the team’s ideology when it comes to free agency. The only route I can realistically see Cease becoming an option for the Cubs is if his market doesn’t end up being as rich as he thought and suddenly becomes more inclined to sign a shorter deal.
Prove us wrong, Cubs. Dylan Cease would be a great signing for this team.
Bruce Levine Sparks Dylan Cease Cubs Rumors
You knew it was only a matter of time before the Chicago Cubs were going to be connected to some big names in free agency and on Saturday Bruce Levine linked the Cubs to a very familiar name in Chicago.
It’s really no surprise that the Cubs will have interest in free agent Dylan Cease as the team has reportedly been trying to get their hands on him since last offseason via trade. There was some smoke in January, when the San Diego Padres were supposedly looking to cut more payroll and the Cubs came up as a potential trade partner. Then, in July the Cubs were one of a handful of teams that checked in with the Padres on the availability of the 2022 Cy Young runner up.
The Cubs have been attempting to add another top of the line pitcher to their starting rotation for a year and Cease will be on their radar this offseason according to Levine.
Cease’s 2025 season was certainly a step back in quality for the right-hander. He was healthy, making 32 starts with San Diego, but Cease struggled to go deep in games, logging a total of 168 innings. That was his lowest innings-total in a season since 2021. Cease only recorded eight quality starts as he ended the year with a 4.55 ERA, 1.33 WHIP and a career high 21 home runs allowed.
On the flip side, Cease didn’t necessarily lose quality in his skill set. He struck out 29.8 percent of the batters he faced, had an expected ERA of 3.46 with a 3.56 FIP.
Including his start in the Wild Card Series against the Cubs, Cease finished the 2025 season with a 2.73 ERA over six starts, striking out 37 batters in 29.2 innings.
By now I think most Cubs fans feel like the team won’t ever actually sign pitchers to huge deals and seeing that Cease is represented by Scott Boras no one is expecting some sweet heart deal. So, how could the Cubs actually be a serious suitor for Cease in free agency? Well, being represented by Borad could end up working out for the Cubs. The super agent will hold out for the biggest deals for his clients, but sometimes that backfires.
It’s not necessarily a loss for the players as they’ll still get paid one way or another, but sometimes they have to wait an extra year or two to capitalize. We’ve seen it recently with Cody Bellinger, Matt Chapman, Jordan Montgomery and Blake Snell, who all signed shorter deals with opt outs heading into the 2024 season. Last offseason Pete Alonso went unsigned until February before the slugger signed a three-year deal with the New York Mets that also included opt outs in his contract.
That’s probably where the Cubs will have interest in signing Cease. I’m sure he was looking forward to a mega payday, but there’s no denying that his down 2025 season will create doubt in the market. Before Carlos Rodon, Cease’s former teammate with the White Sox, signed his $162 million contract with the New York Yankees, the left-handed starter signed a two-year, $44 million contract with the San Francisco Giants that as you guessed it included an opt out.
Maybe Cease holds out, looking for a guaranteed longterm deal, but if his market isn’t as strong as he believes, then the Cubs probably do become extremely interested in signing him to a two or three-year deal with a high AAV that gives Cease the opportunity to opt out if he has a great 2026 season.
We’ll see how the Cubs end up factoring into Cease’s free agent market this offseason.
