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As the Yankees pursue major free agents like Gerrit Cole and Stephen Strasburg, it may be time to look back on how the Yankees have fared in previous offseasons on the free-agent market.

Here is a little history lesson to start things off. According to the Baseball Hall of Fame, The Yankees signed the first free agent ever in 1974. Jim “Catfish” Hunter won his unconditional release from the Oakland A’s after owner Charles Finley refused to pay $50,000 of Hunter’s $100,000 salary in insurance annuities as his contract read. Finley tried paying in cash, but Hunter refused and became the first free agent. The Yankees jumped on the opportunity and paid Hunter $3.2 million for five years.


Years later, hundreds of players have benefited from Hunter’s historic actions, including all of these Yankees.

This is not a ranking of the best and worst, just a sampling of some of the memorable (or unmemorable) moves the Yankees have made via free agency.


+ Reggie Jackson (5 years): 17.2 WAR, 144 HR, 1977 World Series MVP

Jackson signed a five-year contract worth $3.5 million in 1976 according to CBSsport.com. Jackson earned his nickname, Mr. October in pinstripes with three home runs on three straight pitches and a walk in his first PA of a decisive Game 6 of the 1977 World Series.

He had turbulent relationships with manager Bill Martin and owner George Steinbrenner but also had a candy bar made in his honor. Despite the rough sailing, Jackson decided to enter the Hall of Fame as a Yankee in 1993 because he appreciated how the Yankees treated him after his career ended.

Memorable Free Agents

+ C.C. Sabathia (11 years): 30.1 WAR, 143 wins, 17000 Ks

Sabathia was brought in by Brian Cashman to change the morale in the locker room that was dominated by an all-work-and-no-play approach by the Core Four. C.C., alongside Nick Swisher, helped bring some fun to the 2009 Yankees and also helped bring home a World Series trophy, their 27th, and most recent championship.

He was not only asked to change the locker room, but also to pitch well, and he certainly did. With the Yankees, he finished in the top 5 for Cy Young voting in three straight years.

As C.C. aged, he was able to morph his power style of pitching into a finesse approach and gave New York 11 memorable seasons.

+ Hideki Matsui (7 years): 20.4 WAR, 140 HRs, 2009 World Series MVP

Signed out of Japan as a 29-year-old, Matsui wound up second in the AL Rookie of the Year voting and played every game on the schedule in his first three seasons.

Matsui became a fan favorite and like Reggie, ended up being the MVP of a World Series after 3 homers and a 2.027 OPS against Philadelphia in 2009. Like Jackson, his best World Series performance game in the decisive Game 6 when he exploded for 6 RBIs.

+ Mike Mussina (8 years): 35.1 WAR, 123 Wins, 1,278 Ks

Another Hall of Famer the Yankees acquired, “Moose” also helped the Yankees get to two Fall Classics. Despite never winning a World Series with the Yankees, Mussina’s Yankees made it to the postseason in seven of the eight seasons of his Yankee tenure.

Forgettable Free Agents

-A.J. Burnett (3 years): 3.7 WAR, 34 Wins, 513 Ks

Burnett was brought into the Yankee clubhouse alongside C.C. in 2009 for $82.5 million. His Yankee tenure certainly had a different feel than Sabathia’s. Burnett struggled mightily with control, bearing a 4.0 BB/9 as a Yankee with 58 wild pitches.

To shed salary, Burnett was traded to the Pirates after just three seasons.

-Ed Whitson (2 years): -1.9 WAR, 116 Ks

Whitson is another free agent that did not get along with manager Billy Martin, but unlike Reggie’s disdain for Martin, Whitson’s fury resulted in a broken arm for Martin after a fight in a hotel.

He struggled as a Yankee and was consistently booed by fans, even on the road.  Whitson really seemed like he could not handle being a Yankee and wound up negotiating for trade with the Padres and agreeing with the Yankees to forget the remaining 3.5 years on his contract, according to the Society for American Baseball Research.

-Jacoby Ellsbury (6 years): 9.8 WAR, 39 HRs

This free agency signing technically has a chance to turn around and be great for the Yankees. With Hicks hurt and Brett Garnder a free agent, Ellsbury, if healthy, would be a real treat for this Yankee outfield in 2020. However, a plethora of mystery injuries have plagued Ellsbury since 2017.

He is guaranteed over $21 million with a 2021 option that Yankee most certainly will not pick up unless he gets healthy and produces.

-Kei Igawa (2 years): -0.5 WAR, 53 Ks

Some fans were tentative to welcome in Matsui in 2003 and the reason is Igawa. The Yankees swiped Igawa away from under the Red Sox’s clutches in 2002. Theo Epstein and the Red Sox were confident they were going to land the MVP of the Japanese baseball. It seems that would have been for the better as Igawa was horrid in his two seasons with the Big League club.


Alternatively, fans of the Wilkes-Berre/Scranton Yankees were thrilled with this signing as Igawa went on to become the all-time wins leader for the AAA Yankees.

Featured Image: By Jim Accordino - Reggie Powering One,
CC BY 2.0
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