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Pinstripe Alley Top 100 Yankees: #99 Johnny Damon

Four solid seasons in the outfield and some postseason heroics land Damon in the PSA’s Top 100.

Minnesota Twins v New York Yankees Photo by Jim McIsaac/Getty Images

Full Name: Johnny David Damon
Position: Center fielder/Left fielder
Born: November 5, 1973 (Fort Riley, KS)
Yankee Years: 2006-09
Primary number: 18
Yankee statistics: 598 G, .285/.363/.458, 125 2B, 15 3B, 77 HR, 93 SB, 116 wRC+, 11.9 rWAR, 13.3 fWAR


One of the more illustrious members of an already-illustrious enemy-turned-friend club of Boston-to-New York itinerants, Johnny Damon came to the Yankees with his best days already behind him, but nonetheless wrote a worthwhile chapter of his career in the Yankee Stadium outfield. He had already moved to left field by the time he became a starter on a World Series winner for the second time, but with somewhere around 12-13 WAR over four years (depending on who you’re asking), he was well worth the $52 million the Yankees paid him during that time, securing the most recent championship in the Bronx.

Early Life

Born with the name Johnny on November 5, 1973 while his father was stationed at a U.S. Army outpost in Fort Riley, Kansas, Damon, like his predecessor on this list, had a family that moved around a fair bit early in his life. Damon’s father, of course, had much different reasoning that Steve Swisher. As one might have guessed, he was an officer in the U.S. Army. It was in this capacity that he met Damon’s mother, while stationed in her native Thailand. No Thai-born player has ever made an appearance in MLB, and Damon became perhaps the country’s most visible representative in the league, even playing for the Thai national team in qualifying play for the 2013 World Baseball Classic.

In spite of the early movement, Damon’s family settled in central Florida by the time he was ready to start school, and the second child — preceded by a brother, James, two years his elder — spent the rest of the adolescence in the Orlando area. In spite of his larger-than-life personality as a player, Damon wasn’t a natural in the limelight, talking with reporters repeatedly over the years about his struggle with a speech impediment early in elementary school. Even as he excelled at sports, becoming the first four-year starter in the history of Dr. Phillips High School, he recalled his visceral discomfort at being named by Baseball America as the top high school prospect in the country — in a draft class that included Jason Kendall, Shannon Stewart, Todd Helton, Preston Wilson, and, oh yeah, some guy named Derek Jeter.

MLB: USA TODAY Sports-Archive RVR Photos-USA TODAY Sports

Coming into the league’s eye at the end of the speed-demon eighties and just before the steroid-aided power surge of the post-strike nineties, Damon’s combination of prodigious speed, good bat-to-ball ability, and solid pop from the left made him a first-round prospect, though despite BA’s anointment and a Florida Gatorade Player of the Year Award, he was selected after all of those high schoolers (save for the Tennessee-bound Helton).

Damon’s .306 batting line, along with five homers, 23 RBI, and 22 stolen bases as a senior at Dr. Phillips was enough to get him popped with the 35th overall pick of the 1992 draft by the Kansas City Royals, whose amateur efforts were then helmed by Allard Baird. Damon was the fourth pick of the Royals that year, who nabbed him after Michael Tucker (10th overall), Jim Pittsley (17th), and Sherard Clinkscales (31st, and a terrible shame that such a name never broached the big leagues). Not only did Damon outperform all of them, he outperformed everyone, finishing his career with more WAR of all varieties than anybody drafted that year not named Jeter.

Minor Leagues

Damon landed on his feet in the minor leagues, slashing .347/.447/.565 with 12 doubles, 9 triples, and 23 steals in 51 games (50 with the Rookie League Gulf Coast Royals, and one with Advanced-A Baseball City) after signing in the summer of 1992. That was good enough to make him Baseball America’s No. 23 prospect in the game entering 1993, and while his .790 OPS that year wasn’t enough to make him a truly upper echelon prospect, the 59 steals, average-or-better walk and strikeout rates, and good outfield defense made him a high-ceiling major leaguer.

A hot start at Advanced-A Wilmington in 1994 might have had him on track to break camp with the big club in 1995, but as the New York Times noted in their early profile of a minor league Damon, who they called “one of the hottest prospects in Class A ball,” the strike that ended the ‘94 MLB season also put an end to upward mobility in the minor leagues. Damon waited until 1995 to ascend to Double-A, where he tore up the Texas League for a .968 OPS before skipping Triple-A entirely and breaking the surface with Kansas City.

KC Life, A Stop In Oakland, And A Place In Boston History

Even at that early juncture, Damon was still Damon. Much of the interview that constituted that 1994 piece took place in the stands as an observer of his own team, having been suspended for a fight several days earlier. But he also wasn’t quite Damon yet, either; Showing you one of his 1997 baseball cards can get that message across better than words.

Beckett Marketplace

Damon didn’t hit the ground running in the bigs like he did in the low minors, totaling just a .711 OPS (83 OPS+) over his first 338 games, spanning 1995 to 97. As is oh-so-often the case with high school draftees, it took Damon — who was just 21 when he debuted — a few years to mature to the point that he could compete against big leagues. But on bad Kansas City teams, he was allowed to play through the growing pains under manager Bob Boone. Finally, when Tony Muser took over at the end of the 1997 season, Damon began to blossom, finishing with a league-average hitting mark (.779 OPS) for the first time in his career.

The next season, he took it to another level, raising his batting average to .307, his stolen base total to 36, and with improved defense, his rWAR total above 5. It’s rare that a player demonstrates such linear growth over the course of their career, because one year after that, Damon soared even higher, leading the AL with 46 steals and 136 runs, swatting 68 extra-base hits, and receiving a smattering of down-ballot MVP votes. The Royals, having somehow topped out at 77 wins with an outfield alignment of Damon, Carlos Beltrán, and Jermaine Dye, decided to cash in on Damon’s last pre-free agent season, dealing him to Oakland in a complicated three-team deal also including the then-Devil Rays.

Cut to the point: Damon mostly flopped in Oakland, and if he had done any better than an 83 OPS+ and 2.4 rWAR, he certainly wouldn’t have been available to the Red Sox for a price of $31 million over four years. It wasn’t bad money by any means (even then), but nowadays, as a 28-year-old outfielder freshly removed from two straight five-win seasons, he would have gotten a whole lot more than that.

Despite Peter Brand’s insistence to the contrary, Damon more than repaid the Red Sox with 16.5 rWAR, two All-Star appearances, a few more down-ballot MVP votes, and an obvious the heart and soul of a championship clubhouse. His accomplishments in Boston were numerous, and while his postseason performance there was scattershot, he saved the best for the Yankees. Damon homered twice and knocked in 6 of Boston’s 10 runs in the deciding Game 7 of the 2004 ALCS, including an infamous gut-punch grand slam against Javier Vázquez that buried the Yankees before half the fans had a chance to sit down.

Beginning A New Era In New York

By virtue of his early debut, Damon still had yet to play his age-32 season by the time he signed a four-year, $52 million contract in December 2005. That left him a fair bit of prime to give to the Yankees, who scooped him up as the Red Sox bid him adieu.

It’s not quite the same thing as, say, Didi Gregorius replacing Derek Jeter, but despite having a bright star of his own by that time, a self-proclaimed “idiot” whose caveman aesthetic drew GEICO jokes up the wazoo, Damon still had big shoes to fill, as the Yankees had scooped him up more or less to fill the hole left by an aging Bernie Williams, the 15-year incumbent who would spend 2006 primarily in right field and DHing before being getting shuffled out the door the following offseason. Even for the late George-era Yankees, Damon’s addition to an already-star studded outfield that also included Hideki Matsui, Bobby Abreu, and Gary Sheffield (to say nothing of the rest of the lineup) was a massive coup, given the double-blow it dealt to the Red Sox, who had equaled the Yankees with 95 wins in 2005 and were considered easy favorites to re-sign Damon. There was also the fact that just eight months earlier, Damon had been quoted as saying “There’s no way I can go play for the Yankees,” but nobody ever said money didn’t talk!

Unlike some subsequent Red Sox outfielders who signed substantial deals with the Yankees, Damon’s tenure in the Bronx got off to as good of a start as one could hope in such a high-pressure environment. He hit .312 in his first month in pinstripes, and on top of his ninth consecutive season with 100 runs, 30 doubles, and 5 triples, he set a new career high with 24 home runs. All of that, primarily out of the leadoff spot, where he helped solidify the top of a Yankees lineup that Joe Torre had spent several years trying to find any kind of consistency beyond Derek Jeter.

USA TODAY Sports Howard Smith-USA TODAY Sports

Even beyond his grungy aesthetic, Damon had cultivated a reputation as somewhat of a night lifer over the years — in 2004, he claimed that erstwhile Boston skipper Grady Little stopped telling him when he’d be receiving scheduled of days, because otherwise “[he]’d be out partying” — a tendency that, in combination with such a big personality, can often be a recipe for disaster in a place like New York, and even lead to some pretty dark and sad placed.

Damon, however, handled the brighter lights with little more than a shrug, a smooth transition that no doubt him endeared him to a fanbase that can be rather sensitive to change. Short hair and a clean shave wasn’t anything new to Damon, as we saw up above, and as a perusal of mid-2000s sportswriter has demonstrated to me, he was popular with the press, making himself available and open for sound bites more frequently than many players of his stature.

More importantly, Damon simply took care of business on the field. His offense took a step back in 2007, largely dragged down by a brutal April, hitting just .229 as the Yankees went 9-14, their worst opening month in years. Although he hit more like his normal self the rest of the way, he also began to show his age just a bit, and the Yankees already-struggling pitchers weren’t being done any favors by his shaky performance in the outfield.

By the end of the season, Damon was being used primarily in the left field and DH slots, though if part of the goal was to keep his legs fresh, it worked: Damon still stole 27 bases in ‘07, and more importantly, provided steady on-base production at the top of the lineup, setting up pins for Jeter, A-Rod, Matsui, Giambi, and Canó to knock down. And though the Yankees postseason hopes went nowhere that year, it wasn’t for Damon’s best efforts, as it was the lefty’s Game 3 home run against Cleveland that kept that series (and Torre’s career as the New York skipper) alive for another day.

If it helped keep him a little more fresh, then a permanent move to the corners in 2008 is what got Damon on this list, because rather than seeing his peak in the rear-view mirror and beginning to peter out, Damon put together an offensive resurgence in ‘08-’09 that boosted him from “fun guy to remember” territory to “got almost as many Hall of Fame votes as Johan Santana” territory.

At the time, 2008 was the worst Yankees season in recent memory, seeing them miss the playoffs for the first time since the start of their mid-’90s run of dominance, but Damon shone through as one of the few unambiguous bright spots, along with Mike Mussina’s chase for 20 wins. Jeter and Canó produced uncharacteristically down seasons, Brett Gardner and Melky Cabrera had yet to establish themselves in the majors, and the starting rotation included nearly 200 innings of Darrell Rasner and Sidney Ponson. Amid all that noise, Damon’s 125 wRC+ was the highest of his career, and his 3.8 fWAR, second on the team, was a substantial part of why they even made it to 89 wins in the first place.

One of Damon’s best career games occurred during that 2008 campaign as well. As Peter recounted during a past PSA series, he torched his old Kansas City team on June 7th to become the first Yankees player in 74 years to register a six-hit game. That memorable afternoon included a walk-off knock to clinch a chaotic win as well.

Finally, of course, there is 2009, a year in which Damon’s bat held strong, and the ones around him got a lot stronger. He relinquished the leadoff spot back to Jeter for the first time as a Yankee, and while he was definitively losing a step, finishing with fewer than 16 steals in a season (12) for the first time as a pro, he still managed to score 107 runs, third in the AL.

Damon also compensated with some extra power, tying his career-high with 24 jacks and running a 122 wRC+ barely a hair off his previous year’s high-water mark. The short porch had always been an inviting target, but his lefty swing was seemingly tailor-made for the new Yankee Stadium in particular. His homer to cap off walk-off weekend against the Twins in May was one of 17 he clubbed in the Bronx in 2009.

Damon combined with the likes of the “Core Four,” fellow Top 100 Yankees player Nick Swisher, and free agent additions CC Sabathia, A.J. Burnett, and Mark Teixeira to lead New York back into postseason play. They took the AL East with 103 victories and stormed into October looking to write their own post-dynasty legacy.

Although Damon was an inconsistent playoff performer for most of his career, he saved his best for last with the Yankees. He went yard in the ALCS and batted 8-for-22 in the World Series with two doubles, three walks, four RBI, and three stolen bases. Famously, two of those thefts came in Game 4 of the Fall Classic. With the game tied and two down in the ninth, Damon battled Brad Lidge for nine pitches before flaring a single and stealing second. Immediately spying that no one was covering third, he took off and swiped another bag before the play was over.

Alex Rodriguez doubled Damon in, and the Yankees went on to win, 7-4. Jayson Stark noted in an ESPN column the next day that it was a nearly-unprecedented play, amazing even baseball lifers:

“You know how people always tell you that they’ve been in baseball for 40 years, 50 years, and things happen every game that they never saw?” asked Yankees coach Tony Pena, after his Sunday night had turned into Monday morning and he was still trying to digest one of the most astonishing finishes to any game in his 35 seasons in baseball
“Well, I’ve never seen that before,” said Tony Pena. “I never saw that before in my life.”

Damon’s overall performance would’ve gotten him in the conversation for World Series MVP if Hideki Matsui not gone God Mode on everyone. Looking at the big picture, there’s an argument that Damon was really the MVP all along: According to Baseball-Reference, nobody on that Yankees team added more championship win probability than Damon (2.9%), one of three position players — along with Teixeira and A-Rod — to check in above two percent.

Although there was interest in a reunion after New York won it all, that was the end of Damon in pinstripes. He had his salary demands, the Yankees didn’t want to meet them, and that was that. He bounced around between Detroit, Tampa Bay (with whom he belted his final playoff homer), and Cleveland before retiring after 2012, Team Thailand notwithstanding. Damon had been productive in 2011 and entered the 2012 campaign just 277 hits shy of 3,000, but he simply ran out of steam at age 38.

Damon career wrapped up with 56.3 rWAR, 46.3 fWAR, 408 stolen bases, 2,769 hits to his name—more than 600 of which came in New York—and remarkably, nearly an even one-third of his 235 career longballs came in pinstripes. In spite of the cold way that his time with the Yankees ended, it’s hard to ride off much higher into the sunset than with the Commissioner’s Trophy at your side. Even harder than that might be managing to endear yourself, unquestioningly, to both Red Sox and Yankees fans. A unique individual, and a unique career, both within and without the Bronx.

Staff rank: 96
Community rank: N/A
Stats rank: N/A
2013 rank: N/A


Baseball Reference

BR Bullpen


Feinsand, Mark and Bryan Hoch. Mission 27: A New Boss, A New Ballpark, and One Last Ring for the Yankees’ Core Four. Chicago: Triumph Books, 2019.


Previously on the Top 100

100. Nick Swisher
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