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Home»MLB»50 Most Notable Yankees Free Agent Signings Johnny Damon
MLB

50 Most Notable Yankees Free Agent Signings Johnny Damon

JamesMcGheeBy JamesMcGheeJanuary 21, 2026No Comments7 Mins Read
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The 2005 season marked the beginning of the end of an era in Yankees history. In his age-36 season, longtime outfielder Bernie Williams had by far the worst performance of his career, accumulating -1.6 rWAR in 141 games thanks to a combination of lackluster defense and a paltry 86 OPS+. To make matters worse, the team had no obvious replacements on the roster, with Bubba Crosby and his career 47 OPS+ representing the best option. At the same time, despite a small army of power hitters in the middle of the order, the Bombers lacked a prototypical leadoff hitter, pushing Derek Jeter out of his usual second spot and forcing manager Joe Torre to rotate Alex Rodriguez, Hideki Matsui and a young Robinson Canó in Jeter’s old spot in the lineup.

Fortunately for the Yankees, the outfield market was stocked with quality center fielders, with Mike Cameron, Kenny Lofton and Juan Pierre hitting free agency. Ultimately, however, it would be former Boston Red Sox outfielder Johnny Damon – a thorn in the Yankees’ side – who would shave his beard, cut his hair and become the latest Boston fan favorite to defect to the Bronx.

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Johnny Damon
Date of signature: January 3, 2006
Contract: Four years, $52 million

Johnny Damon was no stranger to changing teams. Originally drafted in 1992 by the Kansas City Royals, he spent the first six years of his career in Missouri before being traded to the Oakland Athletics before the 2001 season. After a year in California, Damon signed a four-year contract with the Boston Red Sox. As the core member of the 2004 team that we don’t like to talk about here at Pinstripe Alley, he quickly became a fan favorite in Beantown, and his caveman-like facial hair became not only his defining characteristic, but one of the defining characteristics of the Red Sox. So when he said, “I can’t go play for the Yankees” in May 2005, Boston fans had no reason not to believe him.

Free agency is a funny thing though, especially for Scott Boras’ clients. Heading into his age-32 season, Damon clearly knew this was his last good chance to land a long-term contract, and so Boras went into the winter looking for a seven-year deal for his client. Recognizing his age, the Red Sox held out for a three-year contract, although the center fielder reduced his request from seven to five years. But with the Red Sox front office in turmoil – general manager Theo Epstein had resigned on Halloween that year, and although he would eventually return before the front office in January 2006, the organization had remained directionless and leaderless throughout the free agency period.

And so, when the Yankees agreed to a four-year contract worth $52 million (“Bubba Crosby is our central defender“damn), Damon ignored his earlier comments and didn’t dismiss them out of hand. And when his old friend and Oakland Athletics teammate Jason Giambi called to pitch him in New York, he listened. And in the end, he committed to the razor, agreeing to the deal even as Red Sox general manager of baseball Larry Lucchino spoke to reporters about the team’s impasse in negotiations with their popular center fielder.

This decision paid off for the Yankees. With a career-high 24 home runs and 25 stolen bases (his most in a single season since 2003), Damon stabilized the top spot and earned MVP votes on a dime. His 2007 season, however, saw his OPS and home run total plummet, and while it wasn’t his fault he lost the starting center job to Melky Cabrera – Damon was simply taking the majority of DH at-bats while Giambi was on the shelf with an injury – it was fair to wonder if the Yankees had paid solely for Damon’s decline.

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Fortunately for them, Damon seemed to recognize that he needed a change and he began to reinvent himself as a quasi-power hitter, a change that Brett Gardner would also make later in his career. Now a full-time left fielder, he posted a slash line of .303/.375/.461 with 17 home runs, 27 doubles and 5 triples, while managing to steal 29 bases.

Damon’s first three years in pinstripes were enjoyable, but ultimately it was the 2009 season that transformed Damon from a solid free agent acquisition into a permanent part of Yankees lore. It’s not just that Damon had one of the best seasons of his career, tying a career high in home runs (24) and setting a career high in walks (71). It’s not just that the Yankees won the World Series that season. No, what really cemented Damon’s status as a Yankees fan favorite was the fact that he was at the center of the Yankees’ return to the top. He hit a home run on May 19, the third straight game the Yankees won decisively, helping cement the 2009 Yankees as a team that could never be counted out. He had nine hits in the ALCS, including two home runs, to help the Bombers beat the Angels in six.

But his greatest moments in pinstripes came during the World Series. His numbers themselves were quite impressive – a .364/.440/.455 slash line with eight hits and four runs scored. But it was the ninth inning of Game 4 that made Damon a villain in the city of Philadelphia, cursed by my Philadelphia friends even two decades later. With two outs in the top of the ninth in a 4-4 game, Damon came to the plate against Phillies closer (and professional archaeologist) Brad Lidge. After falling behind 1-2, he fought back to force a full count, then singled to left field. On the first pitch to Mark Teixeira, he stole second, then, noticing that third base was uncovered because Philadelphia’s defense was on team, he picked up third on the same play. Getting the go-ahead third took away Lidge’s best pitch, and the middle of the order fell three spots to put the Yankees one win away from their 27th World Series championship.

Due to his age, the Yankees chose not to re-sign Damon that winter despite his important role in the World Series championship. He went on to sign three one-year deals – with Detroit in 2010, Tampa Bay in 2011 and Cleveland in 2012 – and although he hoped to return to the Bronx in 2013 to help his former team deal with the organization’s numerous injuries, that would be the end of Damon’s baseball career. And while having Damon on the Yankees in 2013 may have been a fun epilogue to his career, in the end, him leaving the Bronx as a World Series champ is perhaps the best legacy for the rare player who became beloved in New York and Boston.

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Sources

Griffin, John. “25 Smartest Moves of the Last 25 Years: Yankees Sign Johnny Damon.” Pinstriped aisle. January 27, 2022.

Hayes, Malachi. “Pinstripe Alley Top 100 Yankees: #99 Johnny Damon.” Pinstriped aisle. October 24, 2023.

“Johnny Damon.” Reference to baseball.

“Johnny Damon.” BR bullpen.

Kepner, Tyler. “The Yankees add their centerpiece: Damon leaves the Red Sox, agrees to a 4-year deal.” New York Times. December 21, 2005.

Kepner, Tyler. “The Yankees beat the Red Sox to get Damon.” New York Times. December 22, 2005.

Marchand, André. “Johnny Damon gives a speech to the Yankees.” ESPN. February 25, 2013.

Sussman, Matthew T. “Boston Might Not Like Johnny Damon Anymore.” Sports in British Columbia. May 2, 2006.

See more from the series “The Yankees’ 50 Most Notable Free Agent Signings in 50 Years” here.

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