2016
The Red Sox lured David Price with a seven-year, $217 million deal. The length of that deal did encompass Boston’s 2018 World Series victory, in which Price played a meaningful role. He made two starts in that series, and won two games.
But when Price became too costly an asset for his reduced role, the Red Sox in February of 2020 shipped him and Mookie Betts to the Dodgers, contributing $32 million to L.A. to make it happen. Price did not take the mound in the Dodgers’ 2020 postseason run.
Greinke re-entered the free agent market and this time accepted a six-year, $206.5 million deal from the Arizona Diamondbacks. That romance lasted three and one-half seasons and encompassed one postseason run. The 2017 D-Backs were eliminated by the Dodgers in the division round, Greinke taking the loss in his only appearance.
It cost Arizona $24 million to get Houston to accept the remaining three years and $104 million of his contract, but it did net 11 postseason appearances, three of them World Series starts.
The other major free agent signings produced questionable benefit. The Cubs locked up Jason Heyward to a deal that continues, paying him $184 million. For that amount, they reportedly got a highly inspirational and possibly pivotal World Series Game 7 locker room speech — oratory ought to count for something — but little on-field production.
The Orioles re-upped slugger Chris Davis for seven seasons at $161 million. They got three years of decent power, no batting average, no postseason hits, and no oratory.
The Tigers committed to free agent Justin Upton to the tune of six years and $132.75 million. Commitments, however, are not what they used to be. When the Tigers deteriorated in 2017, they shipped Upton to the Angels, for whom he has since hit. 267 with no postseason appearances.