Familiar Pattern Emerging as Cubs Miss On Another Top Free Agent

So much for that week or so that we thought the Chicago Cubs would actually try to sign one of the top free agent closers. There’s been some sense of encouragement on the Cubs’ offseason spending after they signed Phil Maton to a two-year deal, but there have now been a couple major free agent targets who have signed elsewhere and both contracts have one thing in common: deferrals.

First, Dylan Cease agreed to a seven-year, $210 million contract with the Toronto Blue Jays, a deal that surprised many as few analysts believed the right-handed pitcher would get remotely close to that figure this offseason. However, the average annual value of Cease’s deal with the Blue Jays will be at about $26 million as the deferred money brings the current value of his contract to $182 million.

Now, closer Devin Williams has signed a three-year deal with the New York Mets.

The deal is reportedly worth $45 million and includes a $6 million signing bonus and more importantly the agreement also has deferred money. According to Will Sammon, $15 million will be paid out in deferrals.

Who knows if deferrals will be eliminated in the next CBA between the league and the players association, but it’s a tool that has become more widely used in these big free agent contracts in recent years. The Cubs included deferred money a decade ago, when they signed Jon Lester and Jason Heyward to their record-setting deals and players since have agreed to take money later on in life in order to secure a bigger contract figure all across MLB.

However, as we see more players take deferrals during this free agent period here’s a reminder that the Cubs are willfully closing off that option for players and thus putting themselves at a disadvantage in negotiations.

Last offseason the Cubs were attempting to sign Alex Bregman, but he ultimately signed with the Boston Red Sox. In that pursuit, fans found out that Cubs ownership will no longer offer deferred money to free agents.

So, keep that in mind as you see free agents agree to big contracts elsewhere. Far too often the Cubs stand in their own way.

(Previous Update)

Hey, hey! The Chicago Cubs finally signed a reliever to a multi-year contract and if Phil Maton doesn’t excite you, then here’s another dose of optimism as we look ahead to the rest of the offseason and the potential of more fire-power coming to the Cubs’ bullpen.

Most fans have been under the impression that pretty much any high-caliber free agent reliever is a no-go for the Cubs based on historical spending and Jed Hoyer leaning toward a cautious approach when filling out the team’s bullpen. It was certainly a bit stunning last week, when Maton’s agreement with the Cubs was reported as a two-year guaranteed deal that also included an option for the 2028 season. The Cubs have not signed a reliever to a guaranteed contract longer than one year since Craig Kimbrel in 2019.

The Cubs have a lot of work to do this offseason to improve the pitching staff and that’s especially true for the bullpen. Out of the eight pitchers who made up the Cubs’ bullpen in the NLDS, six are currently free agents. Maton is a solid first step in upgrading Craig Counsell’s reliever group, but the Cubs are still aiming higher in free agency.

Bleacher Nation’s Michael Cerami, who was the first to report the signing of Maton, added more context on the Cubs’ plans for the bullpen moving forward. No, the Cubs still aren’t targeting closers Edwin Diaz or Robert Suarez, but if you’re intrigued by the idea of the team reuniting two-time NL Reliever of the Year Devin Williams with Counsell, then get ready for a great bit of insight coming your way.

Via Bleacher Nation.

According to a source, the Cubs remain engaged in the impact free-agent relief market even after signing Phil Maton last night. Nothing is thought to be close, but Maton won’t likely be their only established relief signing this offseason. In fact, it sounds like they’re aiming even higher than Maton for their next target.

Who might that be? Well, you can probably keep Edwin Diaz and Robert Suarez off your Christmas list. Those guys are expected to command much more (in both money and years) than the Cubs are likely to commit to any reliever.

But I do think you can keep open the possibility of a Craig Counsell reunion with Devin Williams, or perhaps a Cubs reunion with Brad Keller. Other pitchers in this tier include Pete Fairbanks, who’s already been connected to the Cubs this offseason, and Ryan Helsley, who’s saved 70 games over the past two seasons (3rd most in MLB), though most of those came in 2024.

Brad Keller, Pete Fairbanks and Ryan Helsley would also be significant upgrades and definitely a welcomed sight to the Cubs’ bullpen, but Williams is the guy who has the highest star potential of them all.

Sure, some might freak out looking at his 4.79 ERA with the New York Yankees in 2025, but Williams did settle in after April and finished the regular season with a 3.58 ERA in his last 50.1 innings. Overall, Williams was still putting up monster strikeout numbers, 90 in 62 innings, as his 34.7 K% ranked eighth among qualified relievers in MLB. The right-hander also had a 3.11 xERA, 2.68 FIP and 2.95 xFIP, while recording a 44.6 ground ball rate.

Williams also pitched well in the postseason for the Yankees as the reliever struck out four and only allowed four hits and two walks in four scoreless innings. From 2019 through 2024, Williams posted a 1.83 ERA in 241 appearances with the Milwaukee Brewers. That obviously included five years with Counsell as his manager in Milwaukee.

Williams did suffer a back injury in 2024, when he was sidelined until the end of July. In 2023, Williams earned his second NL Reliever of the Year award after he recorded a 1.53 ERA with 87 strikeouts in 58.2 innings, while closing 36 of 40 save opportunities.

Will we see the Cubs commit $15 million per year or potentially more for Williams? Baby steps, but seeing this as a realistic possibility is much better than the expectations that were set at the start of free agency.