2. Manny Ramirez – 8 years, $160M
Manny Ramirez held the top spot on this list for 15 years before Price came along; the Sox gave him the franchise record-setting contract way back in the year 2000.
No one can argue he wasn’t worth the dough. Over 1,083 regular-season games, he hit a next-level .312/.411/.588 with 274 home runs. He won a Silver Slugger in each of his first six Sox seasons, was an All-Star every year he was here, and led the team to two World Series championships and an assortment of less-successful postseason runs. In 2004, he was their World Series MVP. If not for the performance-enhancing substance issues, he’d be in the Hall of Fame with several of his former teammates. He’s with them in the Red Sox HOF, though.
Ramirez also ended up in Los Angeles; the Sox traded him to the Dodgers in 2008. But like a less protracted Bobby Bonilla, Manny’s contract included many years of deferred salary; the Sox will be paying him until 2027.
3. Adrian González – 7 years, $154M
The Dodgers are a veritable dumping ground for Boston’s biggest contracts, because Adrian Gonzalez ended up there, too, and he’s not the last player on this list for whom that’s the case.
Boston acquired González from the San Diego Padres in December 2010 and by April 2011, he had a massive contract extension. He led MLB with a career-high 213 hits, though it was his first season without 30 or more home runs since 2006. He was an All-Star for the fourth year in a row, won his third Gold Glove in four years, his first Silver Slugger award, and finished seventh in AL MVP voting.
The following summer, he was part of the great salary dump of 2012. The Sox sent him, Josh Beckett, Nick Punto, Carl Crawford, and $11M to Los Angeles for James Loney, Iván DeJesús Jr., Allen Webster, Jerry Sands, and Rubby De La Rosa.