Free Agents Jack Flaherty & Anthony Santander Have New Strategy

Two of the biggest free agents who still haven't been able to land a deal with a new team this winter have each changed their strategy, according to insider Ken Rosenthal.

Unable to land the multi-year deals they've been seeking, both Jack Flaherty and
Anthony Santander "are open to considering short-term deals with high average annual values, according to league sources briefed on their discussions," reports Rosenthal in The Athletic.

It's a strategy that's been used frequently in recent years, particularly by agent Scott Boras after his excessive demands for some of his clients have been shunned by teams around baseball. The strategy has sometimes paid off (as for both Blake Snell and Matt Chapman, who turned their one-year plus option deals into lucrative longer-term deals this past season), but at other times it has backfired (as in the case of Jordan Montgomery last season, who was forced to take a shorter deal, and then went out and had a dreadful season).

Flaherty had a huge bounce-back campaign in 2024, after four injury-plagued years, putting up a 3.17 ERA for the Detroit Tigers and Los Angeles Dodgers, then alternating between great and poor starts in the postseason. It's likely teams are not sold yet on Flaherty being all the way back, and want to see him do it one more time.

As for Santander, it's hard to say what's holding up a deal for him, though Rosenthal speculates that it could be his "career .307 on-base percentage, below-average sprint speed and poor defensive metrics."

Count Pete Alonso as another free agent who still doesn't have a deal as one who might do a shorter-term deal with opt-outs. His agent, Boras, has made a proposal to the New York Mets for a three-year deal with opt-outs. Rosenthal suggests it would have to be worth at least $31.1 million annually, to give Alonso (and, more to the point, Boras) the record for the highest AAV for a first baseman.