Jack Flaherty
Finally, we come to Jack Flaherty who was an ace in the making back in 2019. Flaherty finished in the top 5 in NL Rookie of the Year voting in 2018 and would have gotten more love in the 2019 NL Cy Young vote after posting a 2.75 ERA in almost 200 innings if Jacob deGrom had gone wild that year.
Unfortunately, things started to go sideways after that. Flaherty struggled during the COVID-shortened 2020 season and in 2021, the injury bug started to bite him. Oblique and shoulder issues limited him to just 15 starts in 2021 and shoulder issues plagued him in 2022 as well. While he played the entirety of the 2023 season, he is still clearly not right at the moment as he put up a 4.99 ERA in 29 appearances with the Cardinals and Orioles in 2023.
If Flaherty was willing to take a cheap one year deal and Boston thought there were some mechanical adjustments that would allow him to regain the stuff he showed early in his career, that would be fine. However, it seems more likely that he has some physical things going on that are going to limit him going forward and there is going to be some team that is willing to give him the multi-year deal that his agency, CAA, is going to fight for.
Boston should let someone else pay him and focus on other targets that are more likely to help them in the short-term.