Top 5 Free Agent Signings in Red Sox History

Red Sox
Boston, MA – 7/28/2021: An aerial view of Fenway Park Boston (David L Ryan/Globe Staff ) SECTION: METRO

The Boston Red Sox are a team known for spending money. While that wasn’t the case early on in free agency, the team’s payroll has ballooned in the last 30 years. That spending has led to four World Series Championships this century. But not every free agent signing is created equally. Let’s take a look at the five best free agent signings in Boston Red Sox history.

5. Luis Tiant

This signing didn’t look that spectacular at first. Luis Tiant was signed in 1971 after being released by the Braves who refused to promote him from the minors. Tiant’s first round in the majors with Boston looked like it would land him on the worst free agent signing list. Tiant appeared in 21 games, starting ten and finished with a 1-7 record and 4.85 ERA. It didn’t look good. But the next seven seasons are why he’s on my list. From 1972 to 1978, Tiant would go 121 and 74 with a 3.30 ERA. He was a two time All Star and a constant Cy Young finalist, although he never cashed in the award. In 1975, he appeared in his lone postseason in Boston, and the Red Sox won all four games he started.

Luis Tiant
Luis Tiant is shown in 1972. (Associated Press/WCC)

4. J.D. Martinez

Prior to the 2018 season, the Red Sox were relatively quiet in the free agent market. That changed when they signed J.D. Martinez. Coming off a career year in Arizona, Boston inked him to a 5 year, $110 million contract. That worked out immediately as he was a key cog in the Red Sox winning their fourth World Series title in 14 years. While Boston hasn’t won a title the rest of his tenure, he has been an elite offensive performer, with the exception of the Covid-shortened 2020 season. He’s not worth re-signing unless he’ll take a discount, but he’s proven his worth in Boston.

J.D. Martinez
J.D. Martinez blasted a 444-foot home run to dead center in the second inning Wednesday night against the Orioles.JULIO CORTEZ/ASSOCIATED PRESS

3. Manny Ramirez

Between cutting off the cutoff man and using the restroom inside the Green Monster, Manny Ramirez is definitely the weirdest guy to play for the Red Sox since I’ve been paying attention to them. He may be the weirdest guy to play for them ever, and that says a lot for a franchise that had both Bill “Spaceman” Lee and Dennis “Oil Can” Boyd on it. But, there’s no doubt his signing signaled a changing of the guard for the Red Sox. He would hit .312 in Boston with 274 HRs and 868 RBIs in more than one thousand games with the team. He was a key part of two World Series titles and the 2004 World Series MVP. Given they hadn’t won the World Series in 86 years, the 2004 postseason alone is enough to justify his signing.

Red Sox
Elise Amendola/Associated Press

2. Tim Wakefield

After two years with the Pittsburgh Pirates, Tim Wakefield signed with the Boston Red Sox in 1995. What followed was 17 years of some of the most consistent pitching the game of baseball has ever seen. Wakefield was never the guy to mow people down. But, when his knuckle ball was on, he was tough to hit. He would win 186 games in Boston while posting a 4.43 ERA. Much like Manny, he was integral in two World Series championships. And, if he hadn’t given up the home run to Aaron Boone in the 2003 ALCS, he might be number one on this list. But that honor goes to someone else.

Red Sox
File photo by Dave Roback / The Republican Tim Wakefield pitches during Game 7 of the 2004 ALCS against the New York Yankees in this October 17, 2004 file photo.

1. David Ortiz

Was there ever any doubt Big Papi would be number one? After six unremarkable seasons in Minnesota, the Twins cut David Ortiz in a cost-cutting move. Boston signed him to a one year, $1.75 million dollar deal and never looked back. Ortiz became a ten time All Star and seven time Silver Slugger in Boston. But he was the piece for three World Series teams. Ortiz had the big home run in the 2004 ALCS. He had the big grand slam in the 2013 ALCS that sent that series to Detroit tied 1-1 instead of the Tigers up 2-0. Ortiz was the one leading the way as cheerleader in the dugout in Game Four of the 2013 World Series as Boston trailed St. Louis. The team turned it around and Ortiz was the MVP. Big Papi was the centerpiece for all of that.

What can’t be forgotten about David Ortiz’s time in Boston was his speech in their first home game following the 2013 Boston marathon Bombings. It was a tragic event that devastated a city, a state, a region and a country. When Boston needed someone to lead the way and let them know it was okay to think about sports, Ortiz provided that. “This is our bleeping city,” is still one of the most important lines in a sports speech the city of Boston will ever hear. It was what the city needed right then. Both on the field and off of it, David Ortiz is the best free agent signing in Red Sox history.

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