5: What if the Red Sox spent money at the outset of free agency?
In the mid-1970’s the Red Sox were stacked. Their lineup was filled with MVPs and future Hall of Famers Fred Lynn, Carlton Fisk, Jim Rice, and Carl Yastrzemski, while the rotation was headed by All-Stars Luis Tiant, Bill Lee, Dennis Eckersley, and Fergie Jenkins. There were several reasons why those Red Sox never won a World Series, namely the incompetence of manager Don Zimmer and injuries to Fred Lynn and Carlton Fisk, but the main reason may have been their refusal to participate in free agency.
Over the first five years of free agency, their only significant signing was closer Bill Campbell, who had just one good season in Boston before falling off. The Yankees, meanwhile, were the most active team, signing future Hall of Famers Reggie Jackson, Catfish Hunter, Goose Gossage, and Dave Winfield.
Still, the Red Sox were competitive until the disastrous 1980 offseason, when they traded All-Stars Lynn and Rick Burleson to the Angels after failing to sign them to contract extensions. The final straw was when homegrown star Fisk signed with the White Sox after the Red Sox failed to make him a competitive offer.
The Red Sox window of contention was completely shut after that offseason, as they didn’t finish higher than third place over the next five years. Yet they still had future Hall of Famers in Rice and Yastrzemski and added emerging rookies Wade Boggs and Roger Clemens. However, they always seemed to be a few pieces short, a solution that could have easily been fixed by spending some money on free agency.