Kenny Rogers had a pretty unbelievable career, considering his origins. He was born on November 10, 1964 in Savannah, Georgia, and he spent his childhood on a 16-acre farm in Dover, Florida. He was drafted by the Texas Rangers in the 39th round of the 1982 draft--he was signed for just $1,000--and he kept playing until September 14, 2008. Wow. Even getting to the big leagues after being drafted that late is a challenge, but staying in the big leagues for nearly 20 years is infinitely more difficult. Rogers not only did that, but he also tossed a perfect game in 1994, just the 12th in MLB history at that point.
Rogers spent his first seven seasons with those Rangers, and he performed decently. He was originally drafted as a shortstop and outfielder, but he was later successfully converted to reliever by 1989, and then a starter in 1993. It didn't seem like he would pitch until 43, but he was a somewhat premium arm when he hit free agency after 1995. He had pitched 943.1 innings to the tune of a 112 ERA+, good for 12.9 rWAR. That's certainly good, but George Steinbrenner essentially gave him a blank check after being enamored by his 1995 season. They gave him a four year, $19.5 million contract, and he became the highest paid pitcher on the staff. There was some sentiment among the New York press and inside the Yankees organization that he couldn't handle the market, so he was determined to prove everyone wrong. It didn't work.
Results: 179 IP, 12-8, 4.68 ERA (96 ERA-), 4.83 FIP (100 FIP-), 2.2 fWAR
Even though he was paid $5 million, and he didn't exactly fit that bill, he was the second best starter on the team by rWAR that year, and the third best pitcher overall (Mariano Rivera had an obscene 5 WAR that year). But even so, the fans never truly gave him credit, he had an uneasy relationship with both Joe Torre and George Steinbrenner, and frankly, his postseason performance was horrid. According to Joel Sherman in Birth of a Dynasty: Behind the Pinstripes with the 1996 Yankees, trouble started in February of 1996:
"On February 25, Rogers decided to throw batting practice without the protective screen in front of him and was drilled on his left shoulder by a [Tony] Fernandez line drive. Rogers was so determined, though, to scuttle all the worries that he was not New York tough that he misled Yankee officials, telling them he was fine. But, by mid-March, it was obvious the lefty was not fine, and Joe Torre was furious at being misled. An uneasiness emerged in the Torre-Rogers relationship that would never fully dissipate."
So, originally, the Yankees intended on starting the season with Rogers in the bullpen, and putting Melido Perez in his spot. But when Perez showed some serious red flags in spring training, Torre reinstated Rogers to the rotation. Obviously Rogers wasn't happy just getting the spot by a technicality, so it did nothing to mend their relationship.
Even though Rogers had a pretty decent season, his postseason was just terrible. His first appearance was in the 12th inning of game two, and he issued a four-pitch walk. His first start was in the clinching game of the ALDS, game four, and he lasted just two innings after allowing two runs, and he was lifted for Brian Boehringer. He pitched just three innings in the ALCS, in game four, as he allowed four runs, including a home run to Chris Hoiles. Then in the World Series, Rogers tossed just two innings in game four; he allowed five runs, which could have cost them the series if they didn't come back later in the game for the victory. Ironically, the Yankees won all of Rogers' starts in the postseason, even though he allowed 11 runs in seven innings. If the seemingly poor (as far as public perception goes) regular season didn't sour fans to Rogers for good, the playoffs certainly did.
What did he do after?
Rogers had a World Series ring, exactly what he wanted when he signed his contract, but he wasn't really welcome in New York. He pitched incredibly poorly in the postseason, and while today we have the hindsight of understanding league adjusted ERA, a 4.68 ERA for $5 million wasn't appealing to the average fan, the press, or the organization. He followed it up with an embarrassing 1997, recording an abysmal 80 ERA+ in just 145 innings. He was traded to the A's after the 1997 season for a player to be named later--none other than Scott Brosius. It didn't seem like a great trade at the time, especially because the Yankees were forced to eat $5 million of Roger's contract. I guess Brosius was the silver lining of his contract, because 3.4 WAR for $15 million, in 1997, is a horrible return.
Rogers had a pretty remarkable career aside from his Yankee years. He recorded a 108 ERA+ and 34.6 rWAR after leaving the Yankees, and he tossed over 2000 innings from then on before retiring in 2008. He would play for the Mets, Athletics, Rangers, Twins, and (most notably) Tigers after leaving the Yankees, and he would help lead the Tigers to the World Series in 2006. After his absolutely dreadful 1996 postseason, ten years later he would record 23 scoreless innings. He became the oldest pitcher to record his first postseason win, and one of only two pitchers to record a World Series victory after turning 40. He was a disappointment as far as Yankees free agents go, but he went on to become one of the best older pitchers of the modern era.