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

This week’s mailbag covers just how good a free agent is Jack Flaherty he may be close to his current state, or Alex Bregman It makes sense for the Nationals, the Dodgers suspect they have a predetermined deal Roki SasakiInexpensive right field options for the Pirates, how the Giants can fit into the bat, comparisons Jordan Montgomery, Taijuan Walkeragain Marcus Stromanwhy twins collapse and much more.

Lance asks:

It’s somewhat surprising to see Jack Flaherty kind of iced out, so far, in free agency given the urgency and value placed on quality starting pitching. Could he be in line for a ‘better’ contract if he opted for a long term contract (5 years) at a lower than expected/preferred AAV vs. choosing a short term contract that would see him tied to the Qualifying Offer next offseason?

I see a little a Carlos Rodon relevant here. Rodon had a great 2021 with the White Sox and entered the market without a qualifying offer, but with a questionable health record. So he took two years and $44MM from the Giants via opt out, had his best season, got a QO, and still has a $162MM deal.

Rodon’s Giants contract came after the lockout, and that was an unusual winter for all free agents. But he was only 29 at the time, and I think he had long-term AAV specials as you say to Flaherty. If so, you made yourself a lot of money by not taking this type of deal.

That worked very well for Rodon because he managed well in 2022. Flaherty will need to stay healthy and perform well through 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 an opt-out if it’s multi-year) and get back on the market even with a QO. If he really wants to be strategic, he could sign with a team that might trade him at the deadline, and avoid the QO. If 2025 Flaherty is decent but not great, he might even consider accepting a QO.