Throughout the past few seasons, it is clear that owner John Henry and the rest of the Boston Red Sox organization have been cheap after each season’s end.
The Red Sox are one of the most valuable franchises in sports, yet they barely reach the top third of the league’s payroll rankings, thus giving them an abundance of money to spend. Since they seem unable to spend skillfully, here is exactly how to use up Boston’s spare change this winter:
The biggest name at the top of Boston’s most wanted list has to be Pete Alonso. Unfortunately, Alonso signed a deal with the Baltimore Orioles. While the Orioles offered him a reasonable 5 years $155 million. The Red Sox only offered him an unappetizing 3 years and $85 million with a fourth year option. The Mets’ slugger has totaled 264 home runs and counting since his debut in 2019. He is a two-time Home Run Derby champion, former Rookie of the Year, a Silver Slugger and a five-time All Star.
Nicknamed the “Polar Bear” for his polarizing stature and figure, Alonso was affordable and could have been a key to solving Boston’s struggles at first base.

Another player high on the target list is Toronto’s shortstop, Bo Bichette. With the aging Trevor Story’s enormous contract breathing down the Red Sox organization’s neck, it is time to move on. The Red Sox could simply trade him for some young prospects, but what really matters about this possible trade is the money. This would free up plenty of money for Boston to sign Bichette.
The two-time All Star is one of the league’s most reliable hitters, with a career batting average of .294, and hitting for .311 last year. Bichette is only 27 years old and has only seemed to improve as a player over the years. He could be the organization’s savior at shortstop.
Along with the opportunity lost by Alonso signing with Baltimore, this is another sad example of the Red Sox organization failing to make a sufficient effort at an offseason signing. If they fluke out on more players like Bo Bichette this offseason, it may be the last straw for fans.