Derek Jeter loved to win. He once said that if his grandma challenged him to a race, he would try to beat her and probably enjoy doing it too. Over the course of his legendary 20-year career, that attitude would help Jeter achieve many individual and team accomplishments, most notably winning five World Series championships. So you can only imagine how irritated the captain must have been with players who hurt the Yankees chances of success. This list is about the 15 worst guys that Jeter had the displeasure of watching play alongside him in the Yankee uniform.
The ranking of this list takes into account not only the players who played poorly, but also the players who couldn't stay healthy. Injury riddled players were not ranked as harshly as guys who flat out stunk – but if you failed to contribute to the team's success while taking up a sizable chunk of the payroll, then you hurt the team just as much, if not worse, than the bad players who stayed healthy. That pretty much explains the reasoning for the first name on the list.
15 Carl Pavano
How many injuries does a player have to endure before teammates begin to question if you even want to play at all? Carl Pavano attempted to answer that question after signing a four year, $39.95 million contract before the 2005 MLB season. His career in navy pinstripes started off on the right foot, posting a 4-2 record with a 3.69 ERA in his first 10 starts. That was the best the Yankees would get out of Pavano. In June of that season, he would injure his right shoulder and miss the rest of the season. Then in 2006, he began the season on the disabled list after hurting his buttocks in a spring training game. Then came the back problems. Then the elbow. Next up, two broken ribs in a car accident. He underwent Tommy John surgery in 2007. In 2008, he was taken out of a game due to a hip injury. The media and teammates questioned if the injuries were all legitimate or if he just didn’t want to play. Overall, he finished his Yankee career having made 26 starts in a four year span. He would go on to have consecutive seasons in 2010-11 with over 200 innings pitched for the Minnesota Twins.
14 Stephen Drew
In his short time playing alongside Derek Jeter (just 46 games) Drew managed to perform poorly enough to just make the list. During the 2014 trade deadline, the Red Sox and Yankees made their first trade since 1997. The Sox got Kelly Johnson and the Yankees got Drew. They needed a second baseman for the remainder of the season and they forced Jeter to watch his new double play partner hit well under .200. As a Yankee, Drew batted .150 with three home runs. The Yankees brought Drew back for the 2015 season, but Jeter wisely retired before watching another season of that.
13 Scott Proctor
Proctor’s best season as a Yankee came in 2007, when he led the league in relief appearances as the set-up man to Mariano Rivera. The two seasons prior to that, however, were brutal. He had a combined 5.81 ERA in 2004-05 and gave up 45 earned runs in that span. Now, I know it’s not fair to compare him to Rivera, but in that same time span, Rivera gave up 29 earned runs in over double the innings. Proctor was traded to the Dodgers on the trade deadline in 2007. He made his return to the Yankees in 2011 by signing a minor league contract, but he never replicated his successful 2006-07 seasons.
12 Andy Phillips
Defensively, Phillips was able to play all over the diamond. Offensively, he was a liability. Injuries would lead him into getting regular playing time as a first baseman in 2006. He didn’t do much to impress, posting a slash line of .240/.281/.394 with seven home runs in 246 at-bats. In 2007, he was presented another starting opportunity with injuries to Jason Giambi and Doug Mientkiewicz. He performed better but not good enough for the Yankees to keep him for the following season. He was out of MLB by 2009.
11 Jaret Wright
Jared Wright was drafted by the Indians 1994, but he wouldn’t have a truly successful season in the big leagues until 10 years later, when he was on the other Major League team with Native American influence, the Atlanta Braves. In 2004, he went 15-8 in 32 starts with a 3.28 ERA. He was the Braves best pitcher that year and he took that into free agency. The Yankees threw him a three-year contract worth $21 million, despite Wright only having one impressive season in his eight years at the big league level. He started just 13 games in 2005 and the Yankees offense managed to give him a .500 record at 5-5. His ERA was a disatrious 6.08. The Yankees traded him to the Baltimore in the 2006 offseason, where he would end his career.
10 Enrique Wilson
During the 2001-04 seasons, Enrique Wilson primarily served as the backup infielder. During that time in New York, he compiled a .216/.261/.332 slash line. Oddly enough, he got lots of playing time against Pedro Martinez and went seven for eight against him in 2003. That would be the majority of Wilson’s success as a Yankee, as he accumulated the worst WAR total (-3.0) of any non-pitcher in Yankee history over that three year span.
9 Kevin Youkilis
Acquiring Red Sox players has worked out occasionally for the Yankees (i.e. Babe Ruth), but the signing of Youkilis was not one of them. The Yankees needed a third baseman with Alex Rodriguez beginning the season on the 60-day disabled list, so they awkwardly signed Youkilis to a one-year deal worth $12 million. He had to win over the fans who had booed him for years, but injuries would prevent that from happening. He was placed on the 15-day DL by the end of April and then he underwent season ending surgery in June to repair a herniated disk in his back. Prior to his time with the Yankees, in 2009, both Jeter and Youkilis could have been teammates on the USA World Baseball Classic team, but Youkilis hurt his ankle and wouldn’t play in any games. Apparently, he was never able to stay healthy around Jeter.
8 Jeff Weaver
The Yankees decided to take a chance on the long-haired Weaver by making a trade with the Detroit Tigers. The former first-round pick had a promising 2002 campaign to build upon. Instead he faltered big time in 2003, as opposing batters had a .308 batting average against him in 147.2 innings of work as a starter. He was moved to the bullpen and only made one appearance in the postseason of 2003. It was the World Series against the Marlins, where he gave up a game winning home run to Alex Gonzalez in Game 4.
7 Tony Womack
In 2001, Womack made big contributions to the Diamondbacks upset over the Yankees in the World Series. The Wall Street Journal ranked his game tying double in the ninth inning off Mariano Rivera in game seven as the most clutch hit in baseball history. But his 2005 season with the Yankees was nothing to remember. He had a miserable slash line of .249/.276/.280 and eventually lost the starting job to a young Robinson Cano, who would probably find himself on a top 15 list of Derek Jeter’s greatest teammates. Womack’s War total of -2.2 is the worst single season WAR in Yankee history.
6 Javier Vazquez
In 2003, Vazquez posted career highs in innings and strikeouts for the Montreal Expos. After losing the World Series to the Florida Marlins, the Yankees made a trade in December to acquire Vazquez, who was entering his age 27 season. Many projected the right-hander to win the Cy Young Award, as the Yankees powerful offense was sure to give him plenty of Ws. He would go on to post a 14-10 record with a 4.91 ERA – not horrendous but also not nearly as good as expected. After contributing to the Yankees ALCS collapse to the Red Sox in 2004, Brian Cashman would package Vazquez in a trade to the Diamondbacks that brought future Hall of Famer, Randy Johnson, to the Bronx. The Yankees, however, weren’t done with Vazquez. In 2009, after finishing fourth NL Cy Young Award voting with Atlanta, Cashman traded for him again. Vazquez performed even worse than he had in his first stint with the Yankees and was demoted to bullpen duties. He was released at the end of the 2010 season.
5 A.J. Burnett
Like the man before him on this list, Burnett was another pitcher who had better years before and after his time with the Yankees. He established himself with the Blue Jays as an injury prone pitcher with a high strikeout and walk rate. After a successful 2008 season with the rival Jays, the Yankees inked him to a five year, $82.5 million contract. He pitched decently in the first year of the deal, despite a BB/9 of 4.22. In 2010 and 2011, he would compile an ERA north of 5.00 before being traded to Pittsburgh. The Yankees paid the $20 million of the remaining $30 and Burnett would go on to be one of the Pirates key pitchers for the next two seasons.
4 Kenny Rogers
Kenny Rogers was always up and down during his 20 years in the big leagues, but his time with the Yankees was mostly down. He only played for New York in 1996-97, and while he did have a decent 1996 regular season, he pitched poorly in the postseason. The lefty gave up 11 runs in just seven innings of work. The fans were not happy with him and his $5 million salary. To make matters worse, his 1997 season featured an ERA of 5.65 in 22 starts. After that season, the Yankees did away with him and traded Rogers to the A’s for Scott Brosius.
3 Sterling Hitchcock
In 1989, the Yankees drafted Hitchcock in the ninth round of the draft, but he wouldn’t play with Jeter until 1995. Of course, Jeter wasn’t a regular starter at that time and Hitchcock would be traded before he could play a full season with the captain. He went on to have some success with the Padres, which includes being named the 1998 NLCS MVP. That success would come to an end when the Yankees brought him back in a mid-2001 trade. He pitched in nine games for the Yankees and somehow compiled a 4-4 record with a 6.49 ERA. In 2002, he only had two starts and pitched primarily out of the bullpen. Still, he was not good and he continued to be not good until the Yankees traded him to the Cardinals in 2003. There, he posted a 5-1 record with a 3.79 ERA.
2 Sidney Ponson
A common theme in this article has been the Yankees giving failed players a second chance to redeem themselves with the club. After Ponson pitched poorly enough to get cut by the team in August of 2006, they brought him back in 2008. It was only a minor league contract, but he did get to start 15 games for the Yanks, posting a 4-4 record with a 5.85 ERA. Coincidentally, Jeter had more home runs off Ponson than any other pitcher he faced in his career.
1 Kei Igawa
The signing of Japanese pitcher Daisuke Matsuzaka by the rival Red Sox may have led to one of the worst signings in Yankees history. Igawa signed a five year deal with the Yankees, but only had 13 starts in 2007-08 (12 of those coming in 07), before being demoted to the minors, never to be seen again. He finished his career with a devilish ERA of 6.66. The majority of his time with the Yankees was spent not with Jeter and company, but with pitching coaches in Scranton, trying to change his mechanics.
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