Jacoby Ellsbury was also drafted in the first round by the Boston Red Sox, this time in 2005 and 23rd overall. Two years later, Ellsbury made his debut for the Red Sox, playing thirty-three games and compiling a sparkling .353 batting average over that span. Despite playing only thirty-three regular season games in his rookie season, Ellsbury helped the Red Sox win their second World Series in four seasons.
Ellsbury continued to shine for the Red Sox, collecting seventy stolen bases in 2009. Fast forwarding, Ellsbury once again helped the Red Sox to a world series title, this time in his final season as the Red Sox. Ellsbury earned his right to become a free agent after the season, and to the surprise of money, decided to join the Yankees, singing a seven-year $153 million dollar contract. Ellsbury first two seasons as a Yankee have not been great and he has already begun to see signs of decline. Most notably, Ellbury’s stolen base totals have significantly decreasing, having many wonder if his legs have begun to give out on him. I bet most Yankee fans would not mind returning him to the Red Sox at this point.