David Ortiz
This is the big one and has to go down as the greatest free agent deal the Red Sox ever made. David Ortiz is quite simply the single-most important player in Red Sox history. In addition to his countless clutch hits during his fourteen seasons in Boston, he was the face, heart, and soul of the Red Sox.
In the winter of 2002, Ortiz was released by the Minnesota Twins and became a free agent. At the urging of Pedro Martinez, then-GM Theo Epstein signed Ortiz to a non-guaranteed $1.25 million deal which only went into effect if he made the team coming out of spring training. He did and as we all know, the rest is history.
While originally signed to help give the Red Sox some depth at first base, Ortiz ended up being the team’s DH for the rest of his career and what a hitter he was. He hit .288 with 31 home runs and 101 RBI in his first year with the club and was a big reason they got all the way to game seven of the 2003 ALCS before losing in heartbreaking fashion.
His 2004 season was even better as he hit .301 with 41 home runs and 139 RBI. Through 2008 he’d combine with Manny Ramirez to make one of the most potent hitting tandems in all of baseball. With those two guys coming in the three and four spots of the order, opposing pitchers had no way to pitch around either of them and the two Sox sluggers made them pay.
Ortiz cemented his place as a Boston sports legend with his numerous clutch and game-winning hits during the 2004 postseason, most notably his series-winning home run in game three of the ALDS against the Angels and his two game-winners in games four and five of the ALCS.
Ortiz was one of the main reasons the Red Sox finally ended their drought in 2004 and had he never played another game for the team, he’d already have been a Boston sports god. Instead he helped the team win two more World Series in 2007 and 2013 while mentoring each new generation of homegrown Red Sox stars.
From Kevin Youkilis to Dustin Pedroia to Mookie Betts and everyone in between, Ortiz was the one constant for the Red Sox from 2003 to 2016. For his Red Sox career, he hit .291 with 483 home runs and 1530 RBI. He set the franchise single-season record for home runs with 54 in 2006 and retired in 2016 at the age of 41 after hitting .315 with 38 home runs and 127 RBI in that final season.
“Big Papi” was a larger than life personality who always had a smile on his face but played with an intensity that was fearsome. He was synonymous with the Red Sox for fourteen years and was there to comfort fans and steel their resolve in the face of tragedy in 2013 when he declared that “this is our ****ing city!” before the first game played after the Boston Marathon bombings.
While he spent most of his career as a DH, Ortiz looks to be a lock for Cooperstown when he’s eligible in 2022 thanks to his exploits at the plate with the Red Sox. Without Ortiz, the Red Sox don’t win the World Series in 2004 and from there, who knows how history might have unfolded? Instead, they’re the winningest franchise (in terms of championships) in all of baseball this century.
For all of that and then more, David Ortiz is the greatest free agent signing the Red Sox have ever made.