3. Don't forget about pitching
The Red Sox's development of quality pitching has been stagnant for 15+ years, with Brayan Bello possibly being the tiny break in that pattern. Boston has been forced to trade and buy the arms necessary to win, and they have been successful four times this century—time to make it five.
For the 2023 season, Boston checked in 10th in the American League in pitching, breaking it down to 12th in starting and 5th in relief. Chris Martin and Jansen are two bright-spot signings by Bloom. Bloom went cheap on starting pitching and the team no longer needs a staff of Corey Kluber's and Garett Richards.
The Phillies' recent signing of righty Ace Aaron Nola gives insight into the market. Nola received a 7-year deal for $172 M, and I would expect the same for Japanese phenom Yoshinobu Yamamoto, who has been connected to a legion of MLB teams. Yamamoto would be my primary target to focus on in the free agent market, but there are many more with varying degrees of ability.
Trades are also a possibility, and last season, we saw two high-profile free agents - Justin Verlander and Max Scherzer - move at the deadline. As winter rolls along, Breslow will be on the horn attempting to match up with another GM/CBO to satisfy mutual needs. Boston has prospects and money, and the first order of business is pitching.