Best Red Sox free agent contracts of the last 20 years: #2 - Adrian Beltré
Adrian Beltré might take top billing on this list had he been in Boston for more than one year. The Red Sox masterfully swooped in and took advantage of a soft market for the third baseman after a down year in 2009. They picked him up on a reasonable one-year, $9 million deal, and that 2010 season proved to be the springboard to a powerful back half of the Hall of Famer's career.
From 2010 to 2018, Beltré was worth 48.9 bWAR with the Red Sox and Rangers, outpacing his early-career numbers from 1998 to 2009 (44.6 bWAR) with elite-level production throughout his 30s. That all began with that stellar year in Boston.
Beltré played for 21 years and he only had one better year, at least in terms of bWAR, than he did in 2010. In 2010, the slugger led the league with 49 doubles along with 28 home runs, 102 RBI and a .321/.365/.553 slash line. He earned the first All-Star selection of his career to that point and his offensive exploits netted him the second Silver Slugger of his career, as well.
He parlayed that into a five-year, $80 million deal with Texas, and he wound up spending the rest of his career with the Rangers. But for one summer, Beltré was beloved by Red Sox Nation — and rightfully so.
Worst Red Sox free agent contracts of the last 20 years: #2 - Carl Crawford
Early in his career with Tampa Bay, Carl Crawford was a stud. A four-time All-Star, the speedster averaged 4.0 bWAR a season, led the league in stolen bases four times and put it all together in his final year with the Rays, bringing home a Silver Slugger and Gold Glove to set himself up for a massive payday in free agency.
Boston handed the outfielder a seven-year, $142 million deal on the heels of his monster 2010 season and things went sideways almost immediately. It proved that betting on a guy who made his name with his legs in his 20s attempting to maintain his athleticism into his 30s isn't the best idea.
His OBP fell below .300 in his first year in Boston and a historic September collapse from the club did little to endear their big-dollar outfielder to them. Due to a wrist injury, he didn't make his 2012 debut until mid-July and appeared in just 31 games before undergoing Tommy John surgery. Two days later, he was included in the blockbuster trade with the Los Angeles Dodgers that saw Crawford, Josh Beckett, Adrián González and Nick Punto head west in exchange for Iván De Jesús, James Loney, Allen Webster and two players to be named later.
That ended Crawford's Red Sox tenure, and if you ask any Boston fans, they'll tell you it was two years too long. A disaster from the start, this one is an all-time bust.