No team has won more World Series in the 21st century than the Red Sox, and owner John Henry deserves much of the credit for that.
The principal owner of the Red Sox since 2002, Henry has watched the Red Sox break the Curse of the Bambino, win four World Series titles and become a perennial contender. However, since the Sox's last championship, they've only made it back to the postseason once, and that has raised questions about the team's leadership.
While many of the Red Sox's moves have been questioned, no decision has been more maligned than trading Mookie Betts to the Dodgers. In February of 2020, after being unable to extend Betts, Boston shipped Betts and David Price to Los Angeles in exchange for Alex Verdugo, Connor Wong and Jeter Downs. The Dodgers immediately extended Betts with a 12-year, $365 million contract.
To say this trade didn't pan out for the Sox is an understatement. Betts has remained one of the best players in baseball, making four All-Star teams and winning four Silver Sluggers and two Gold Gloves since moving to LA. Meanwhile, Verdugo was slightly above average during his tenure in Boston, Wong hasn't made much of an impact even five years later, and Downs was designated for assignment in 2022.
Mookie Betts' trade from the Red Sox in 2020 will cast a long shadow over John Henry's ownership
Not only did the Red Sox get absolutely fleeced in this trade, but the psychological impact of trading the team's best player still hasn't worn off. The trade continues to cast a long shadow over the team even years after it happened, and fans still haven't forgiven the team's ownership. It's a move that can only be explained by Henry's unwillingness to spend money to keep a generational, homegrown talent in Boston.
While the Red Sox have had plenty of success under Henry, the Betts trade is still difficult to swallow. The trade sent the message that Henry didn't care about winning enough to spend for Betts. It doesn't take away from the four World Series titles that the Sox have won, but it is one of the worst trades in recent memory in any sport.