Johnny Damon is one of the few players to win World Series rings for both the Boston Red Sox and New York Yankees while serving as a starting position player. Damon shocked Red Sox Nation when he signed as a free agent with the rival Yankees in January of 2006, just a season removed from having been part of the first Red Sox club to win the Fall Classic since 1918. In 2009, Damon a second ring with the Yankees.
It shouldn't have been a surprise that Damon has switched teams so often in his big league career. As a child, Damon lived all over the world - Germany and Japan to name a few - as an Army brat. After his family settled in Orlando, Florida, Damon quickly established himself as a standout baseball player. By his senior year in high school, Baseball America rated him the top prep player in the nation. In 1992 he was drafted in the first round by the Kansas City Royals.
Damon quickly proved that he was a talented player, hitting .347 as an 18-year old in Rookie ball, stealing 59 bases the next year in Single-A, and batting .343 with 16 homers and 26 steals for Wichita at Double-A before being called up by the Royals in August of 1995. The quick left handed batter was ready for the big leagues - he spent the next five years as a starting outfielder for the Royals, batting near the top of the order much of the time. It was with KC that he earned the nickname "Captain Caveman" because of his hairy bearded appearance. His best year in Kansas City came in 2000 when he batted .327 with a league-best 136 runs and 46 steals while also banging out 214 hits. But with the Royals going nowhere, the club packaged Damon in a three-team, seven-player trade that sent him to Oakland. In the deal, the Royals received young shortstop Angel Berroa, who later won the AL Rookie of the Year Award in Kansas City.
In the expansive ballpark in Oakland, Damon struggled, batting just .256 with a career-low slugging percentage of .363. As their leadoff hitter, Damon still scored more than 100 runs and the team advanced to the post-season as a wild card after winning 102 games. In the ALDS against the Yankees, Damon's bat caught fire - he hit .409 with nine hits and two steals in the A's five-game loss. It was a rental deal for the A's really, because Damon was a free agent after the 2001 season. His post-season performance helped draw more clubs to the table, and Damon signed a four-year million contract with the Boston Red Sox.
The Red Sox had parted ways with troubled center fielder Carl Everett after the '01 season and were anxious to plug Damon into that spot and also slot him into the leadoff role. Hitting in front of sluggers David Ortiz and Manny Ramirez, Damon had his best years, scoring more than 100 runs in each of his four years in Boston. The Sox advanced to the post-season in three of the four years Damon was there, and Damon provided many clutch hits. Perhaps his most famous performance came in Game Seven of the 2004 ALCS against the Yankees. Damon hit two home runs at Yankee Stadium, including a grand slam in the second inning that stunned and silenced the crowd.
In Boston, Damon was a crowd favorite, with his aggressive play in the outfield and on the basepaths, as well as his penchant for fouling off pitches in epci batter/pitcher duels. It seemed he would almost always end up drawing a walk or looping c single into the outfield. He also maintained his excellent success as a basestealer - swiping 98 bases for the Sox while being thrown out just 21 times.
Damon inked his million deal with the Yankees in 2006 and had four good seasons with the Bombers, helping them to the post-season three times. In cozy Yankee Stadium, Damon hit a career-best 24 homers in 2006 and 2009. In the latter season he was instrumental in helping the Yankees to the World Series title, hitting a pair of homers in the ALCS against the Angels and batting .364 in the Fall Classic against the Phillies. In New York, Damon teamed at the top of the lineup with Derek Jeter, hitting in front of Alex Rodriguez, Jason Giambi, and other sluggers in the Yankee lineup.
Indications are that the Yankees wanted to resign Damon when his contract expired, but agent Scott Boras and the front office were fresh off other disagreements over player contracts and that helped contribute to the impasse that ensued. Damon proceeded to spend the next three seasons signing one-year deals with the Detroit Tigers, Tampa Bay Rays, and finally the Cleveland Indians in 2012 after sitting out spring training waiting for an offer. As of 2012, Damon was about 250 hits shy of the 3,000-hit plateau, a personal goal he had his sights set on. Without reaching that target, Damon will probably have a difficult time getting enough support for the Hall of Fame. However, with nine straight seasons of scoring at least 100 runs, more than 230 career homers, over 400 career stolen bases, and his track record as a clutch post-season performer, he has earned a place as one of the best leadoff hitters of the early 2000s.