Adrian Gonzalez, Carl Crawford, Josh Beckett
In the offseason before the 2011 season, the Red Sox went out and made perhaps the biggest combined splash of the winter: signing Carl Crawford to a seven-year, $142 million contract and trading for Adrian Gonzalez, who they then signed to a seven-year, $154 million extension. Crawford never really took off in Boston, but Gonzalez was an instant star, leading the team to the best offensive numbers in the American League for most of 2011 and was regarded as a strong candidate for AL MVP.
But after the September collapse, in which the Red Sox blew an 8.5 game lead in the wild card standings to miss the playoffs, the team plummeted in 2012 under new manager Bobby Valentine.
Josh Beckett, who was the 2007 ALCS MVP and Boston’s ace of the pitching staff for half of a decade, began to fall out of favor with fans and management alike due to his poor performances and reported lack of professionalism for the team and his job.
So on August 26, 2012, the Red Sox decided to make the most expensive total trade in history, sending Gonzalez, Crawford, and Beckett, along with infielder Nick Punto, to the Los Angeles Dodgers for James Loney, Allen Webster, Ivan De Jesus, Rubby De La Rosa, and Jerry Sands.
The trade, which exchanged over a quarter of a billion dollars in salary, will save the Red Sox more than $250 million in salary through 2018. Though seen at the time as the Red Sox giving up on the 2012 season, it ultimately ended up paying off, as Boston, free from high salary constraints, was able to sign key 2013 players such as Shane Victorino, Mike Napoli, and Jonny Gomes, who have the Red Sox at first place in the American League halfway through the 2013 season.