Projecting a Red Sox-Jack Flaherty contract in free agency

The regular season isn't quite over, but the Boston Red Sox are basically out of the playoff question now.

They're four games back of the Twins, behind the Mariners and red hot Tigers, so it would take egregious losses all across the board for their closest competitors to make it to October.

So, the Red Sox should be thinking ahead. Get through what's left of the season and hopefully put up a winning record by then. Next, direct attentions to the free agent market to try to find pieces that will put this team into a better position this time next year.

Juan Soto, Pete Alonso, Alex Bregman, and Corbin Burnes are the big highlights on the market this year. All will fetch millions and multiple years from whatever team they land with. Burnes very well could be an option for Boston, but if even he turns out to be a little too expensive for the Red Sox, there are plenty of other good, available pitchers they can chase.

Mark Feinsand recently named the Red Sox as a potential landing spot for Jack Flaherty, who's had an incredible bounce back year with the Tigers and Dodgers. Flaherty won't go cheaply, but he'll still be cheaper than Burnes. If the Dodgers don't get to him first, what could a potential contract in Boston look like?

What offer could potentially tempt Jack Flaherty to the Red Sox in free agency?

Flaherty signed a one-year deal with the Tigers last year worth $14 million, which was probably the best he was going to get after all of his struggles in 2023. He made it worth the Tigers' while, giving them 18 starts and a 2.95 ERA, one of the best in the AL, before being traded to LA at the deadline. He's 28, so if he's looking for a multi-year deal, three or four would be the best bet for the buying team.

Zachary Rymer at Bleacher Report posited four years and $72 million for Flaherty, for an $18 million AAV. $18 million sounds about right, but four years might be a little too much of a gamble for a pitcher who struggled so much in Baltimore as recently as August of last year.

We'll keep Flaherty at $18 million a year, but take the years down to three for a $54 million total. A mutual or club option for a fourth year also seems plausible; it gives the Red Sox an out if Flaherty somehow loses his magic after this season.

Flaherty isn't a bad option for the Red Sox at all. He proven that he can still be a solid middle-rotation starter, which incentivizes potential suitor teams to take a chance on him again despite his previous struggles. If the Red Sox find that they really need to stand out from the rest of the pack, then a guaranteed fourth year, maybe with an option for a fifth, might be necessary, but they'll want to keep an eye on him through the postseason to see if he's really worth pulling out all the stops for.

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