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MLB Mailbag: Flaherty, Nationals, Sasaki, Pirates, Giants, Twins

January 23, 2025
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This week’s mailbag covers how free agent righty Jack Flaherty might approach his current situation, whether Alex Bregman makes sense for the Nationals, accusations of the Dodgers having a predetermined deal for Roki Sasaki, low-cost right field options for the Pirates, how the Giants could fit in a bat, a comparison of Jordan Montgomery, Taijuan Walker, and Marcus Stroman, why the Twins collapsed, and much more.

Lance asks:

It’s somewhat surprising to see Jack Flaherty kind of iced out, up to this point, in free agency given the urgency and value placed on quality starting pitching. Would he be in line for a ‘better’ contract if he opted for a long-term (5-yr) contract at a lower AAV than expected/preferred versus opting for a short-term contract that could see him saddled with a Qualifying Offer next offseason?

I’m seeing a bit of a Carlos Rodon parallel here.  Rodon had an awesome breakout 2021 with the White Sox and hit the market without a qualifying offer, but with a dubious health track record.  So he took two years and $44MM from the Giants with an opt-out, had an even better season, got the QO, and still landed a $162MM deal.

Rodon’s Giants contract came after the lockout, and that was an unorthodox winter for all free agents.  But he was only 29 at the time, and I imagine he had lower-AAV longer-term offers like you mentioned for Flaherty.  If so, he made himself a lot of money by not taking that type of deal.

That worked out so well for Rodon because he dominated in 2022.  Flaherty would need to stay healthy and pitch well in 2025 to get the $100MM+ deal he’s likely seeking.  He doesn’t turn 30 until October, so he’s in a good position to take a short-term deal (with opt-outs if it’s multiyear) and go back to the market even with the QO.  If he really wanted to be strategic, he could sign with a team that is likely to trade him at the deadline, and dodge the QO again.  If Flaherty’s 2025 is decent but not great, he could also consider accepting a QO.

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