Cubs To Re-Sign Caleb Thielbar

Thielbar, 39 in January, spent his entire big league career prior to the 2025 season with his hometown Twins. He signed a one-year, $2.75MM contract coming off a down showing in his final year with Minnesota and bounced back in a major way with Chicago.

In 58 innings this past season, the South Dakota State product notched a sharp 2.64 earned run average and 25 holds — the latter tying him with Brad Keller (also a free agent this winter) for the team lead. Thielbar struck out 25.5% of his opponents, limited walks at an excellent 5.9% clip, and kept 40.7% of the batted balls against him on the ground (a career-high mark). He tacked on another 3 2/3 scoreless frames in the postseason.

While he doesn’t throw particularly hard (92.8 mph average fastball in ’25), Thielbar still managed to post a roughly average swinging-strike rate and an above-average strikeout rate thanks to dominant performances from his curveball and slider alike. Opponents hit just .135 and slugged .231 against the former while batting .169 and slugging .254 versus the latter. Thielbar dominated left-handed hitters (.161/.211/.276) and right-handed hitters (.205/.248/.342) alike during his lone season with the Cubs.

Thielbar is the third free-agent addition to the Cubs’ bullpen this winter, joining fellow southpaw Hoby Milner (one year, $3.75MM) and right-hander Phil Maton (two years, $14.5MM). Thielbar and Milner give manager Craig Counsell a pair of experienced southpaws, both of whom he’s previously managed, and create the potential for a trio of southpaws, should Luke Little also make the club. Thielbar, Milner and Maton will combine to help bridge the gap between the rotation and young closer Daniel Palencia.

There’s still room for Chicago to make further additions to the bullpen, which has at least three spots earmarked for relatively untested arms. Each of their bullpen pickups thus far has also been relatively low-cost in nature, leaving room for a significant addition elsewhere on the roster. The Cubs have been at least loosely tied to top free agents like Ranger Suarez, Tatsuya Imai, Alex Bregman and Eugenio Suarez, among others.