Andy Pettitte is arguably the Yankees' best starting pitcher since Whitey Ford, but his tenure could have easily ended after just four and a half seasons in the Bronx. The trade deadline can often lead to questionable decisions, and the Yankees faced a big problem during the 1999 season--what could they do about Pettitte?
The lefty joined the starting rotation as a rookie during the Yankees' 1995 run to the AL Wild Card, finishing with a 111 ERA+ in 175 innings, good for a third-place finish in the AL Rookie of the Year voting behind the Twins' Marty Cordova and the Angels' Garret Anderson. He shot to stardom in '96 as he avoided the sophomore slump in grand style, dominating the American League with a 5.6 rWAR season, winning an AL-high 21 games in 221 innings with a 129 ERA+. The Yankees won the AL East and Pettitte pitched well in two ALCS starts against the division rival Orioles, then rebounded from a horrible World Series Game 1 to dominate the defending champion Braves in Game 5 over 8 1/3 scoreless innings. The Yankees were World Series champions, and they had an ace in the making. Pettitte had an even better year in '97, pitching to a personal Yankee-best 156 ERA+ with a 2.88 ERA in 240 1/3 innings, good for a career-high 8.4 rWAR. However, the Yankees only won the Wild Card, and they were ousted in the Division Series against the Indians; Pettitte lost both of his playoff starts.
Despite his ALDS struggles in '97, nobody thought that the 26-year-old southpaw would experience a sudden decline in performance. That's exactly what happened with Pettitte though, as he was only mediocre on a dominant '98 squad that won 125 games between the regular season and playoffs on the way to another World Series title. Pettitte threw more innings than anyone on the starting staff with 216 1/3, but he was overshadowed by his teammates David Wells, David Cone, and "El Duque" (Cuban rookie Orlando Hernandez). He pitched to a 104 ERA+ and saw his walk rate jump from 2.4 BB/9 in '97 to 3.6 BB/9 in '98. Pettitte really slumped down the stretch, posting an ugly 6.14 ERA in August and September, although he did pitch well in two of his three playoffs starts. This disappointing '98 was a cause for concern entering the '99 campaign; the Yankees reportedly even discussed trading Pettitte to the Blue Jays for Roger Clemens prior to sending Wells to Toronto instead. The Yankees were not the only ones unsure about Pettitte's future:
Scouts around baseball believe that the quality of Pettitte's stuff is diminishing gradually, much in the way Jim Abbott regressed and was released before his 30th birthday. At the same time, Pettitte's salary is skyrocketing -- he earned $3.8 million in 1998, and he will be eligible for arbitration after each of the next two seasons. If the Yankees' executives agree with the assessment of others that Pettitte's ability is diminishing, they could trade him now. - New York Times, 12/10/1998
The Yankees ultimately kept Pettitte in '99. Despite some elbow soreness in spring training, they were hopeful that he could rebound. He threw shutout ball for six innings in his first start of the season against the Tigers on April 17. It would be his last scoreless outing for about four long months. Pettitte was trashed in the majority of starts after that until the trade deadline. From April 24 through July 28, he had a 5.98 ERA in 18 starts, and opposing batters were hitting .304/.385/.469 against him. As the trade deadline approached, Pettitte had an ugly 5.93 ERA over the previous calendar year, 28 regular season starts. Needless to say, owner George Steinbrenner was frustrated:
Before the staff meeting, Steinbrenner said in a telephone interview that Pettitte had had ''plenty of opportunities to show us he's getting better.''
''I've been saying all along they've got to get him straightened out,'' he said.
Pettitte may make $7 million or more next year. ''How can he look at that after the type of year he's having now?'' Steinbrenner asked.
If the Yankees do not want to pay Pettitte that much money next year, they must either trade him now, when interest is heightened by the pennant races, or try to unload him in the off season, when other clubs will wait to see if the Yankees simply do not offer Pettitte a contract. ''Here's what the general manager is facing,'' Steinbrenner said, ''either he's going to be a free agent, or you don't tender him a contract and you get nothing in return.'' - New York Times, 7/30/1999
Pettitte looked as ugly as ever in his last start before the deadline against the sub-.500 White Sox. He gave up three runs on eight hits and two walks in just 3 1/3 innings, bizarrely changing tactics mid-pitch on his final delivery of the game in a sidearm slider laced for a go-ahead single. Joe Torre came to the mound to get him and Pettitte walked off, unsure if he would be wearing pinstripes in his next start.
As the July 31st deadline approached, the sense was that Pettitte would be traded. His value was diminished, but they were talking to the Phillies, Giants, Orioles, and Pirates about Pettitte. The most widely-reported trade possibility as a supposed deal with the Phillies. The Yankees would trade Pettitte to Philly in exchange for three prospects: righty starter Adam Eaton (the Phillies' top pick in '96), lefty starter Anthony Shumaker, and center fielder Reggie Taylor. The two pitchers had both spent time in Double-A and Triple-A in '99, and Shumaker even made his MLB debut. None of them had especially sterling minor league numbers, but the Yankees seemed determined to get something for their beleaguered lefty.
General manager Brian Cashman, pitching coach Mel Stottlemyre, and Torre all pleaded with Steinbrenner to reconsider sending Pettitte away. After long talks, the Boss relented and Pettitte stayed a Yankee through the end of the deadline. Buoyed by the reassurances of confidence, Pettitte pitched much better over the season's final three months into October, and only really faltered in his World Series start against the Braves. The Yankees won the World Series, and in the off-season, the Yankees re-signed Pettitte to a three-year, $25.5 million deal with an $11.5 million player option for 2003.
The contract turned out to be a steal for the Yankees, who received 13.3 rWAR and a 115 ERA+ from Pettitte over the next four seasons. The Yankees won another World Series in 2000 and two more AL pennants in '01 and '03. Eaton was eventually traded to the Padres and lasted 10 seasons in the majors from 2000-09, but only had a career 84 ERA+ and 2.3 rWAR. Shumaker's eight games in '99 turned out to be his only MLB season, as he journeyed from organization to organization, eventually flaming out in Independent ball by after the '02 season. Taylor appeared in 260 games for the Phillies, Reds, and Devil Rays from 2000-05, but never did anything of much worth either.
None of those prospects ever panned out, and the Yankees were rewarded for their faith in Pettitte. An old baseball cliche is "Sometimes the best trades are the ones you don't make." Never was this more true for the Torre-era dynasty Yankees with Andy Pettitte in '99.
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