The Chicago Cubs have agreed to a one-year deal with free-agent lefty, a league source confirmed to North Side Baseball. The news was first reported by Jesse Rogers of ESPN, on Twitter. Thielbar, who will turn 39 in January, returns after a strong season as a setup man for the 2025 Cubs.
Few 10-year major leaguers have followed a path as unlikely as Caleb Thielbar’s. Drafted by the Brewers in the 18th round in 2009, he was released just months later. After a stint in independent ball, he drew interest from his hometown Minnesota Twins, with whom he appeared in parts of three seasons before washing out in 2015. He briefly passed through the Padres organization without reaching the majors, then signed with the Marlins late in 2016 only to be released again the following year. Thielbar spent 2016 and 2017 in independent leagues and the next two seasons in the minors with the Tigers and Braves.
On the verge of stepping away from playing to pursue coaching, Thielbar received another call from the Twins. This time, he resurrected his career, contributing parts of five additional seasons in Minnesota before joining the Cubs last winter on a modest contract.
Despite the nomadic and tenuous nature of his career, Thielbar’s pitching foundation has always been sound. He has defied the typical aging curve, frequently adding velocity rather than losing it. Training at Driveline Baseball helped transform him from a finesse left-hander reliant on command and craft into a viable high-leverage option. Now sitting around 93 mph and capable of touching 95, he pairs that velocity with a deceptive left-handed delivery.
Multiple breaking balls make him a versatile weapon, rather than a strict matchup option. Bringing back a true slider (to work as a complement to both his sweeper and his big, slow vertical curveball) was a key change for 2025, allowing Thielbar to better manage contact and fill up the strike zone.
Alongside newcomer Hoby Milner, Thielbar figures to anchor the left side of the Cubs’ bullpen depth chart, with fringy arms Luke Little and Riley Martin as secondary options and swingman Jordan Wicks a candidate to slot in for longer work. Chicago had interest in fellow southpaw Foster Griffin, returning from a sojourn in Japan, but Griffin will get a chance to start for the Washington Nationals, which he would have had little chance to do in Chicago. Once Griffin elected to sign with Washington, the Cubs pivoted to the reunion with Thielbar.
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