Chicago Cubs Recent Free Agent Pitching Addition Named Team's Worst Contract

One of the needs the Chicago Cubs had when they entered the offseason was to add depth to their starting rotation.

Veteran Kyle Hendricks, who was the longest-tenured player on the team, departed early in free agency, signing a deal with the Los Angeles Angels. That created an opening behind Shota Imanaga, Justin Steele, Jameson Taillon and Javier Assad.

A few in-house options existed, such as their top pitching prospect Cade Horton or Ben Brown, the latter of whom made his MLB debut in 2024 and was quite productive across 55.2 innings as a starter and reliever.

Both youngsters could find their way into the rotation at some point in 2025, but the Cubs opted to add veteran options in free agency to shore things up.

Inexplicably, they didn’t go near the top of the market in search of a true impact arm to bolster their staff.

Instead, they went right to the bargain section of free agency out of the gate, something that could come back to haunt them as the opportunity to put some real distance between their National League Central rivals existed and was not taking advantage of.

One of the players they came away with was Matthew Boyd, who agreed to a two-year, $29 million deal that includes a $15 million mutual option for 2027. So, the veteran lefty could end up earning $44 million over the course of three years if things go well.

That is certainly a risky proposition given his injury history, which is a major reason why Tim Kelly of Bleacher Report has named Boyd’s contract as the worst one Chicago currently has on its books heading into the 2025 season.

It is easy to see why a team would take a chance on him after he had a 2.72 ERA across eight starts and 39.2 innings in the regular season with the Cleveland Guardians. He struck out 46 and his ERA+ of 151 was excellent.

The strong performance carried into the playoffs, where he made three starts and tossed 11.2 innings. He allowed only one earned run, resulting in a 0.77 ERA with 14 strikeouts.

Those are numbers worth gambling on, especially for someone who is going to slot into the back half of a starting rotation.

However, contingency plans need to be in place since counting on Boyd to make 25-plus starts could be disastrous.

He hasn’t made more than 15 appearances in a single campaign since 2019, when he started 32 games for the Detroit Tigers.

That eight-game sample with the Guardians was also the first time in his career he had a FIP under 4.10 as a starter; in 10 relief appearances with the Seattle Mariners in 2022, he had stellar 3.19 FIP and 1.35 ERA.

The Cubs are hoping they get the form of Boyd that was on display in Cleveland during 2024, but they need it to be for more than 11 appearances for the contract to be worthwhile or else the statement of Kelly could be proven correct.

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