Looking back at the most hyped prospects in recent Red Sox memory

TORONTO, ON - APRIL 27: Xander Bogaerts #2 of the Boston Red Sox hits a single against the Toronto Blue Jays in the sixth inning during their MLB game at the Rogers Centre on April 27, 2022 in Toronto, Ontario, Canada. (Photo by Mark Blinch/Getty Images)
TORONTO, ON - APRIL 27: Xander Bogaerts #2 of the Boston Red Sox hits a single against the Toronto Blue Jays in the sixth inning during their MLB game at the Rogers Centre on April 27, 2022 in Toronto, Ontario, Canada. (Photo by Mark Blinch/Getty Images) /
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BOSTON – JULY 04: Jacoby Ellsbury #46 of the Boston Red Sox runs the bases against the Tampa Bay Devil Rays July 4, 2007 at Fenway Park in Boston, Massachusetts. (Photo by Elsa/Getty Images)
BOSTON – JULY 04: Jacoby Ellsbury #46 of the Boston Red Sox runs the bases against the Tampa Bay Devil Rays July 4, 2007 at Fenway Park in Boston, Massachusetts. (Photo by Elsa/Getty Images) /

Red Sox CF Jacoby Ellsbury

Few players have a more complicated Red Sox legacy than Jacoby Ellsbury. On one hand, he was a two-time World Series champion, an All-Star, an MVP candidate, and a three-time stolen base champion. On the other hand, he was frequently injured, only hit more than ten home runs once, and, worst of all, signed a seven-year contract with the hated Yankees.

Before any of this, however, Ellsbury was a five-sport athlete at Madras High School in Oregon. Though he put up eye-popping football and basketball numbers, baseball was his best sport, as he hit .537 with 65 stolen bases in his senior year. He committed to Oregon St. and turned a first-team All-American honor into a first-round selection by the Red Sox in 2005.

From the very first time he stepped onto a professional baseball field, Ellsbury was one of the best base stealers out there. He stole 23 bases in 35 games in 2005, 41 more in 2006, and another 41 in 2007 before getting called up at midseason.

On top of this, Ellsbury was a skilled hitter, albeit one with very little power, posting at least a .298 average at every level of the minors, and that streak would continue upon his arrival in Boston. Ellsbury hit an outstanding .353 in 33 games, a mark that was so good that he earned a spot on the postseason roster and hit .438 in the team’s series sweep of the Rockies.

Like Buccholz, Ellsbury’s career would be defined by what he wasn’t rather than what he was. His 2011 was an all-time season, a 30-30, .321/.376/.552 monster that would have won MVP if not for an even more historic Justin Verlander effort.

In his other six seasons with the Red Sox, however, he never hit double-digit home runs or match any of those triple slash numbers. That season was also sandwiched between two seasons where he played a combined 92 games.

Those injuries would be a major reason why the Red Sox felt comfortable letting Ellsbury sign with the Yankees, and that proved to be a wise decision. Ellsbury’s speed quickly faded, and the injuries eventually became too much.

He would play just four out of the seven seasons on his contract and somehow is now more unpopular among Yankees fans than Red Sox fans. Go figure. In a fun turn of events, he showed up at Fenway Park last season in his old Red Sox jersey as a part of Dustin Pedroia’s retirement celebration. The opponent watching from the other dugout? The Yankees.