The Chicago Cubs made a bit of noise when they signed Phil Maton to a two-year deal-a rare move for a franchise that's been notoriously cautious when it comes to investing in relievers. But just as fans started to feel a flicker of optimism, two major bullpen arms came off the board elsewhere, both on deals that included deferred money-something the Cubs have shown little interest in offering. And that reluctance may be limiting their ability to land top-tier talent.
Let’s start with the big moves. First, Dylan Cease inked a surprising seven-year, $210 million deal with the Toronto Blue Jays.
The headline number raised eyebrows, but the real story is in the structure. Thanks to deferrals, the present-day value of the contract drops to around $182 million, with an average annual value sitting at roughly $26 million.
That kind of financial maneuvering allowed the Blue Jays to stretch their dollars while still landing a premier arm.
Then came the New York Mets, who added two-time NL Reliever of the Year Devin Williams on a three-year, $45 million contract that also includes a $6 million signing bonus. Again, deferrals played a big role-$15 million of the total value will be paid out over time, smoothing the annual hit and giving the Mets more flexibility in the short term.
This is becoming a clear trend across Major League Baseball: deferred money is no longer just a creative accounting trick. It’s a legitimate tool teams are using to stay competitive in the free agent market. The Cubs, however, are choosing not to play that game.
That decision could be costing them. Just last offseason, the Cubs were in the mix for Alex Bregman before he signed with the Boston Red Sox.
Reports at the time revealed that Cubs ownership had drawn a hard line-they would no longer include deferred money in free agent contracts. That stance might have made sense a decade ago, but in today’s market, it’s a self-imposed handicap.
The irony? The Cubs were once ahead of the curve on this.
They used deferrals when they signed Jon Lester and Jason Heyward to headline-grabbing deals in the past. But now, as more and more free agents agree to backloaded contracts in exchange for higher total value, the Cubs are opting out-and it’s putting them at a disadvantage.
That’s not to say the Maton signing isn’t a step forward. It is.
The Cubs haven’t handed out a multi-year deal to a reliever since Craig Kimbrel in 2019, so locking in Maton through at least 2027 (with an option for 2028) signals a willingness to invest in bullpen stability. But Maton alone won’t fix a bullpen that’s been gutted since the end of the season.
Six of the eight relievers who appeared in the NLDS for the Cubs are now free agents. That’s a massive hole to fill, and Maton is just the start.
According to league sources, the Cubs are still active in the relief market and are aiming higher than Maton for their next move. That’s encouraging, but it also raises the obvious question: how high are they really willing to go?
Don’t expect the Cubs to be in the mix for Edwin Díaz or Robert Suarez-both are expected to command more years and dollars than the Cubs are likely to commit. But the idea of a reunion between Craig Counsell and Devin Williams had been floating around as a plausible fit. That’s off the table now with Williams heading to Queens, but it underscores the level of talent the Cubs were reportedly exploring.
Other names still in play include Brad Keller, Pete Fairbanks, and Ryan Helsley. Keller has familiarity with the organization, Fairbanks has already been linked to the Cubs this offseason, and Helsley has quietly become one of the league’s most consistent closers, racking up 70 saves over the past two seasons-third-most in MLB.
But let’s circle back to Williams for a moment, because he was arguably the best fit on the board. Sure, his 4.79 ERA with the Yankees in 2025 might raise some eyebrows, but that number doesn’t tell the full story.
After a rough April, Williams settled down and posted a 3.58 ERA over his final 50.1 innings. The strikeout numbers were still elite-90 Ks in 62 innings-and his advanced metrics backed up the performance: a 3.11 xERA, 2.68 FIP, and 2.95 xFIP, along with a 44.6% ground ball rate.
In the postseason, he was nails-four scoreless innings, four strikeouts, and just six baserunners allowed. And let’s not forget his dominant run in Milwaukee under Counsell, where he posted a 1.83 ERA over 241 appearances from 2019 to 2024.
Injuries have played a part-Williams missed time in 2024 with a back issue-but when healthy, he’s still one of the most electric arms in the game. In 2023, he earned his second NL Reliever of the Year award with a 1.53 ERA, 87 strikeouts in 58.2 innings, and 36 saves in 40 chances.
That’s the kind of impact arm the Cubs could use right now. And while $15 million per year might’ve been a stretch based on the team’s recent track record, the fact that they were even in the conversation is a sign of progress-albeit slow and cautious.
So where does that leave the Cubs? Still searching.
Still trying to patch together a bullpen that can support a playoff-caliber roster. Still operating under financial constraints that other teams are finding ways to work around.
And still, perhaps, standing in their own way.
The Maton deal is a start. But if the Cubs want to keep pace in an increasingly aggressive free agent market, they’ll need to rethink their approach-especially when it comes to deferred money. Because right now, the teams willing to get creative are the ones landing the difference-makers.