"When the Cubs signed Alex Bregman, I immediately thought about when they landed Jon Lester 12 years earlier. Okay, my immediate thought was "Holy shit!" But after giving the move a little time to marinate, it became clear that the deals are similar in terms of establishing the Cubs' legitimacy as contenders for both big free agents and the NL pennant. There's also something to be said for both players being paid for their intrinsic qualities as much as their performance."
"Lester was just about to turn 31 when he joined a Cubs team that had been downright bad for several seasons, providing a veteran presence to a team that hadn't yet learned how to win. While Lester was tremendous with the Cubs, finishing second in the 2016 NL Cy Young voting, his best years were already behind him and his performance understandably eroded over time. But ask anyone whether the contract was worth it and you'll get unanimous approval."
"Bregman is about 14 months older than Lester was in 2015 and he's coming to a team that already had a taste of success, but the concept is similar. He's a grinder who isn't likely to replicate the massive output he gave the Astros early in his career, and it's possible - likely, even - he experiences a downward trend in production similar to what we saw with Lester."
The Cubs signed Alex Bregman in a move comparable to their Jon Lester signing, signaling legitimacy to attract top free agents and contention for the NL pennant. Jon Lester joined as an almost-31 veteran, providing leadership to a struggling club and delivering strong early performance despite later decline; the contract remained widely regarded as worthwhile. Bregman, slightly older, joins a more successful Cubs team and projects as a grinder unlikely to match peak Astros production. The Cubs appear willing to overpay on the back end to secure elite or stabilizing production early and increase championship prospects.
Read at Cubsinsider
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