For years, then-Red Sox GM Theo Epstein had lusted after San Diego Padres first baseman Adrian Gonzalez. With his sweet left-handed stroke and power, Gonzalez was putting up 30-40 home runs every year and had a swing that seemed tailor-made for Fenway Park.
After years of trying to pry him away from the Padres, Epstein was able to do so in the winter of 2010 when he sent a package of Red Sox prospects, including Anthony Rizzo, to San Diego for Gonzalez. For the first half of the 2011 season, it looked as though it paid off in spades as the Red Sox signed him to a seven-year extension and locked him up long-term.
The 2011 Red Sox were cruising and Adrian was mashing, hitting 22 home runs heading into the All-Star break. However, after participating in the home run derby at the Midsummer Classic, he only hit 5 homers the rest of the way and finished with 27 on the season to go along with a .338 average and 117 RBI.
After the Red Sox historic collapse in September 2011, his power outage continued in 2012 when he hit .300 with 15 home runs and 86 RBI in 123 games. It turned out that Gonzalez was also not a good clubhouse guy, being outed as a clubhouse lawyer and one of the players who undermined manager Terry Francona in 2011, which led to the skipper’s firing.
In August of 2012, Gonzalez was shipped out to the Dodgers along with Josh Beckett and Carl Crawford in a massive salary dump. A guy who the Red Sox couldn’t wait to get ended up being one they couldn’t wait to get rid of.
Even worse for Boston, Rizzo became a Gold Glove first baseman and All-Star for the Cubs, helping them win the 2016 World Series while hitting 218 home runs (and counting) along the way.