2. Whit Merrifield
As the Blue Jays' everyday second baseman in his age 34 year, Whit Merrifield managed to have his best offensive year since 2021. His production has declined gradually since his 2018-2019 peak in Kansas City, but he still managed to play in 145 games in 2023 for Toronto and was named an All-Star for the third time in his career in 2023. In two years for the Blue Jays, Merrifield batted .274/.319/.394 and stole 26 bases, harkening back to his role as three-time AL stolen base leader.
Merrifield and the Blue Jays declined his mutual option at the beginning of the offseason, but he hasn't made any indication that he intends to retire. The Red Sox could consider a short-term, relatively cheap contract — Spotrac calculates his market value at $6.4 million a year, while MLB Trade Rumors projects a two year, $18 million contract — for a player who is still clearly capable of speed on the base paths as well as reasonable offensive numbers (he hit 11 home runs and batted in 67 runs in 2023). And, as the team that signed Justin Turner at 37, the Red Sox aren't strangers to signing older players who manage to do good, everyday work for them.