The Chicago Cubs are making moves, although the maneuverings are coming at a glacial pace so far this offseason.
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From the end of November to the present tense, the collective effort of Chicago’s front office has amounted to three relievers being signed– Phil Maton, Hoby Milner, and a returning Caleb Thielbar.
On a team with glaring needs that include a front-of-rotation starter, a proven closer, and a top bench asset to help fill the gap left by a departing Kyle Tucker, the lack of a high-priority, big-time acquisition is starting to frustrate fans.
Actually, up until now, the Cubs’ offseason has been better defined by who they’ve lost.
The offseason of loss
Sep 24, 2025; San Diego, California, USA; San Diego Padres starting pitcher Dylan Cease (84) delivers during the second inning against the Milwaukee Brewers at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
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Aside from the likely loss of Tucker, the Cubs have also whiffed on free agents Dylan Cease and Devin Williams, who would take more lucrative deals by the more financially daring Toronto Blue Jays and New York Mets, respectively. Then, of course, there’ve been the free agents loosely tied to the Cubs, like Kyle Schwarber, Pete Alonso, Robert Suarez, Emilio Pagan, and Ryan Helsley, who signed elsewhere.
Now, the Cubs can add another loss in the form of 2025 bullpen anchor piece Drew Pomeranz, who just signed a one-year deal as a free agent with the Los Angeles Angels.
Goodbye to Drew Pomeranz
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May 31, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) delivers against the Cincinnati Reds during the first inning at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
The 37-year-old Pomeranz had a career rebirth last season under the guidance of manager Craig Counsell and pitching coach Tommy Hottovy after being acquired from the Seattle Mariners for cash considerations in late April. At the time, the lefty hadn’t pitched in the majors since 2021 and was, by his own admission, pretty much at the point of hanging up his glove.
Instead of retirement, Pomeranz would end up having a stellar year, posting a 2.17 ERA in 49.2 innings over 57 appearances as a Cubs middle reliever/setup man. In the playoffs, he was also rock-solid with a 1.50 ERA in six innings pitched.
However, the Cubs didn’t seem all too eager to re-sign him, possibly doubting his ability to sustain the success he had last season. When the front office re-signed the lefty Thielbar on Tuesday, after picking up another lefty reliever in Milner, the writing was pretty much on the wall that Pomeranz would have to move on.
The partially rebuilt Cubs bullpen now consists of Daniel Palencia, the returning Thielbar, Maton, Milner, Porter Hodge, and long-relief/swing man options Colin Rea, Javier Assad, Ben Brown, and Jordan Wicks. There will hopefully be at least one or two more noteworthy pickups before spring training.
Chicago Cubs welcome back one-time top prospect
Jun 7, 2024; Kansas City, Missouri, USA; Kansas City Royals designated hitter Nelson Velazquez (17) hits a walk-off fielderÕs choice during the ninth inning against the Seattle Mariners at Kauffman Stadium. Mandatory Credit: Jay Biggerstaff-USA TODAY Sports
Meanwhile, the Cubs did make a minor addition with the re-signing of one-time top outfield prospect Nelson Velazquez. It’s being reported that the Puerto Rico native has been signed to a minor league deal.
The soon-to-be 27-year-old was once a highly regarded prospect in the Cubs organization with multi-tool capabilities. In 2023, however, he was traded away from a jam-packed Cubs outfield picture to the Kansas City Royals for pitcher Jose Cuas.
He showed good promise early on in his Royals stint, hitting 14 home runs in 133 at bats, but then completely fell apart in 2024, where he struggled to make the Mendoza line. He was relegated to minor league duty until being released in late May of last season. Velazquez then signed a deal with the Pittsburgh Pirates in September, which didn’t stick.
The Cubs will give their former prospect another go as they are currently in need of outfield depth. When operating at full speed, the right-hander has some pop in his bat, above-average speed, and the ability to play all three outfield positions. He’s yet to prove that he can succeed over the long haul at the major league level, but his role– if he has any– will just be as a fourth outfielder and/or emergency call-up.
With almost two months still to go before 2026 spring training, the Cubs will clearly need to get more done. Time will tell whether the heavy lifting is still to come.
Chicago Cubs lose another bullpen anchor, then get more disappointing bullpen news
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