9) Worst Red Sox trade: Acquiring Adrian Gonzalez for Anthony Rizzo and then trading him
Was this actually a bad Red Sox trade? Adrian Gonzalez was an amazing player for Boston. The problem is all of the context around it.
Gonzalez was dealt by the San Diego Padres to the Red Sox on December 6, 2010. Eric Patterson would get paired later on with the initial trade costing Boston Rey Fuentes, Casey Kelly, and Anthony Rizzo.
Gonzalez had a monster 2011 season for Boston shortly after signing a seven-year extension, batting .338/.410/.548 while leading the league with 213 hits. How could this trade possibly be a disaster? He was pretty good in 2012 as well, batting .300/.343/.469 in his 123 games. Then came the problem. The Red Sox had issues and in order to help dump some major salaries off of the payroll, Gonzalez was among the players sent to the Los Angeles Dodgers for not much at all.
The Red Sox may have won the Gonzalez deal with the Padres, but it did cost them Rizzo who would go on to have a ton of success later on with the Chicago Cubs. They were left without a truly good first baseman which, fortunately, didn’t hold them back from winning the World Series in 2013.
Having this trade on the list is more of a testament to how good the Red Sox have been at avoiding bad trades. As we move on, they’re going to get more painful.