Cubs’ $42 Million Gamble on a Veteran Reliever Backfires Badly: Once Seen as the Bullpen Savior, the Move Has Become One of the Worst Value Contracts in Baseball

Chicago believed this move would fix their late-game pitching woes — but it’s backfired badly.
By Chris Landers | 20 minutes ago

The Cubs entered the offseason with one clear priority: stabilizing a bullpen that had been anything but reliable. President Jed Hoyer opted for a bold move, acquiring veteran reliever Ryan Pressly from the Astros in January. The cost? A promising young arm in Juan Bello and a commitment to pay $8.5 million of the $14 million Pressly is owed for 2025 — a hefty price considering team ownership’s tight financial reins.

But the gamble hasn’t paid off. As May winds down, Pressly sports an ugly 5.71 ERA, inflated by a nightmare outing against the Giants in which he allowed eight runs. That disaster effectively ended his time in the ninth inning, as manager Craig Counsell has avoided using him in high-leverage situations since. While that one game was a glaring low point, deeper metrics are troubling: Pressly’s strikeout and whiff rates have nosedived, his walks are up, and his velocity is down — not exactly the profile of a dependable late-inning weapon.

Ryan Pressly
Ryan Pressly

It’s a stinging miss for the Cubs, especially given the context. With Tom Ricketts unwilling to match the spending of MLB’s big-market heavyweights, every financial decision comes with trade-offs. The $8.5 million spent on Pressly now looks like a sunk cost that could’ve gone to more productive use.

To their credit, the Cubs have managed to patch things together without Pressly closing games, leaning on arms like Porter Hodge (currently injured), Brad Keller, and Danny Palencia. Still, even if the bullpen holds up, the Pressly acquisition stands as a major offseason misstep — one that underscores the challenges of trying to compete while operating under strict budget constraints.

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