Sunday, January 11, 2026

Newsletter Excerpt, January 11, 2025 -- "Cubs Sign Alex Bregman"

 

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I look to Cubs history for the best comparison. In the winter of 2014-15, Theo Epstein went into the market for a highly-rated 31-year-old free agent and paid him $155 million. From December 13, 2014:

The Lester signing is the first step in the next phase, shaping the talent into the form of a championship team. The core of young position players allows the Cubs to pay, even overpay, for starting pitching, something they don't have much of in their system. Lester may not be a #1, but he's a solid #2 with a track record of providing innings and whose skills have not deteriorated as he's reached 30. There's some risk here, but signing Lester -- signing a high-priced starting pitcher -- was the next phase of the plan.

The Jon Lester signing is the Alex Bregman signing, the use of money to back up a strong player-development run. The former led to a November dogpile in Cleveland, and the latter may produce a similar outcome.