Best Red Sox free agent contracts of the last 20 years: #1 - JD Martinez
During the span of his five-year, $110 million deal with the Red Sox, JD Martinez was an All-Star four times, a Hank Aaron Award recipient, had a 135 OPS+ and helped Boston win a World Series championship. Not a bad return on investment for the club, eh?
Martinez got things started with a bang in 2018, his first season with the team, leading the league with 130 RBI and 358 total bases to go along with an OPS over 1.000. His 43 home runs were the most by a Red Sox player since Big Papi belted 54 in 2006. Boston put it all together as a club that year, winning 108 regular-season games before winning it all and vanquishing the Dodgers in the Fall Classic.
The next year, a relative 'down' season compared to the year prior, Martinez still hit 35 home runs, surpassed 100 RBI and posted a .939 OPS in 657 trips to the plate. He left no doubt: this guy was the offensive powerhouse the team had been searching for in the post-Ortiz era.
Martinez led the league with 42 doubles in 2021 and actually bested that mark in his final year with the Red Sox, racking up 43 two-baggers in 2022. In those five years with Boston, he established himself as one of the game's premier extra-base threats - and that contract proved to be worth every penny for the team.
Worst Red Sox free agent contracts of the last 20 years: #1 - Pablo Sandoval
Picking between Pablo Sandoval and Carl Crawford for the top spot on this list was a challenge, because both were complete dumpster fires in Boston.
A three-time World Series champion with the San Francisco Giants (2010, 2012, 2014), Sandoval hit the open market on the heels of the '14 title and signed a five-year, $90 million deal with the Red Sox. His free-swinging ways in his first year with Boston didn't go unnoticed and the fanbase soured on him quickly after he batted just .245/.292/.366 in 2015.
Sandoval was told to get in shape that winter and lose weight. He showed up to Fort Myers the following spring looking heavier than ever, denying anyone from the team told him to drop some pounds. His Red Sox tenure only worsened from there.
He tallied all of six at-bats in 2016 due to a shoulder injury, and although he returned to action the following spring, a 62 OPS+ and below-average defensive marks led Boston to designate him for assignment in July with more than three years still left on his contract. The Red Sox had to foot another $41 million after dumping him — one of the worst free-agent signings in recent memory.