MLB's No. 5 Worst Trade in History: The Trade That Lost a World Series

Josh BenjaminCorrespondent IDecember 3, 2010

Before making a name for himself in the National League, Ted Lilly was a top prospect in the Yankees organization
Before making a name for himself in the National League, Ted Lilly was a top prospect in the Yankees organizationDoug Pensinger/Getty Images

The year was 2002.  The city was New York.  The beloved New York Yankees, having just endured a heartbreaking loss to the Arizona Diamondbacks in the previous World Series, looked to regain their stride by signing valuable free agents.  Among these free agents were first baseman Jason Giambi, a guaranteed home run hitter who had gained rock star status in Oakland in recent years, and pitcher Mike Mussina, who General Manager Brian Cashman hoped would bring a bit of extra experience to the team’s pitching staff.  All in all, things looked positive for the upcoming season


Joining Mussina in the starting rotation were longtime Yankee veterans David Wells and Andy Pettitte, with a 39-year-old Roger Clemens and Orlando “El Duque” Hernandez rounding things out.  However, looming in the background among these pitching Adonises lay an unknown.  He was a young left-handed pitcher acquired two offseasons ago in exchange for Japanese bust Hideki Irabu and in a few starts in 2001, he had proven his ability to pitch at the major league level despite some flaws that with experience, he would easily overcome.  This young pitcher’s name was Ted Lilly, and it was George Steinbrenner’s impatience with him that would ultimately cost the New York Yankees a World Series Championship.


When the 2002 MLB All-Star Break arrived, the Yankees sported a record of 55 wins and 32 losses, with a 2 game lead over the rival Boston Red Sox.  The team’s offense was powering its way to wins, but the pitching, while adequate, left something to be desired.  Mike Mussina didn’t show the same domination he had with Baltimore, and once lights-out Roger Clemens was slowed by a sore groin.  Fan favorite Andy Pettitte spent a couple of months on the disabled list with a strained elbow and Hernandez just appeared to have lost it.  As a result, the young Lilly was called upon for some spot starts.  Yet, despite posting a 3.40 ERA, he compiled a record of 3 wins and 6 losses in just 11 starts.  Then, in his classic impatient fashion, owner George Steinbrenner ordered Cashman to trade for some pitching, no matter what the cost.  The team was already stocked with high-priced veterans, so it only made sense that the league minimum earning Lilly be the one to go.  Thus, on July 6, 2002, in a three-team deal, the Yankees acquired pitcher Jeff Weaver from the Detroit Tigers, with Lilly going to the Oakland Athletics and first baseman Carlos Peña moving from Oakland to Detroit.


Right from the start, the trade appeared to have a negative effect for both Oakland and the Yankees.  Weaver, who at that point and throughout his career has struggled to find his “stride” in pitching, gave up 12 home runs in 15 appearances with the Yankees, despite posting a record of 5 wins and 3 losses in 8 starts.  The following season, he fared much worse.  In 32 appearances (24 starts), Weaver managed only 7 wins compared to 9 losses, with an earned run average of 5.99.  Lilly’s statistics in his first full season in Oakland were not much better.  Rushed into rounding out a rotation already dominated by Oakland’s “Big Three” (Barry Zito, Mark Mulder and Tim Hudson), gave up 24 home runs in less than 200 innings of work, despite posting 12 wins and an earned run average of 4.34.


Now, those reading this article are probably wondering, “Alright…you say this is the fifth worst trade in baseball history.  Neither of these players have proven themselves to be Hall-of-Famers, so what do you have against this trade?”


The backlash of this trade appeared in the 2003 World Series.  The Yankees faced the Florida Marlins in this particular Fall Classic, and a good series was expected as the Marlins, led by manager Jack McKeon and young star pitcher Josh Beckett, were a Cinderella story and expected to give the Yankees a run for their money (no pun intended).  After splitting the first two games in New York, the series was taken to Florida for the next three games.  Weaver was on the playoff roster as the long reliever, and did not make his first appearance until the fourth game.  Going into Game 4, the Yankees led the series two games to one and expected their pitching to handle the young Marlins easily.  However, the game went into extra innings, with the score tied 3-3.  In the bottom of the 11th inning, Yankees manager Joe Torre decided to rest lights-out closer Mariano Rivera and let Weaver pitch, thinking that being called upon in a clutch situation would boost his confidence.  It first appeared to be a move that paid off as Weaver retired all three batters he faced in his first inning of work.  His fastball was at its best and he appeared to be in total command.


However, what one must understand about Jeff Weaver is that throughout his career, he has had too much confidence in his fastball.  When he is pitching well in a game, rather than change speeds and use his other pitches, he seems to rely solely on the fastball.  This explains why throughout his career, he has given up more home runs than the average major league pitcher should.  That being said, when Marlins shortstop Alex Gonzalez led off the bottom of the 12th inning with the score still tied, it doesn’t seem surprising that after an eight pitch at-bat during which many of the balls were fouled off, that Weaver felt cocky about his fastball and thus decided to throw one right down the middle of the plate.  The young hitter, liking the pitch he saw, commenced to hit it over the left field wall for the game-winning home run, evening the series at two games apiece.  The Marlins would then win the next two games and their second World Series.


Opinions on this trade may vary, but I’m just curious: what if Lilly hadn’t been traded?  What if he had been on the mound that night instead of Weaver?  Despite his limited experience, he was well on his way to establishing himself as a talented young finesse pitcher (one who relies more on his pitches’ location rather than velocity).  Had he been on the mound against Alex Gonzalez and his breaking ball was at its best, I have no doubt that he could have handled a young and inexperienced team like the Marlins with ease and maybe the Yankees would have eventually won the game.


On top of that, perhaps he would have finally developed into the pitcher scouts said he had the potential to be: not a particularly hard thrower, but he can put hitters away when he needs to.  Yet, he had the misfortune of being on the Yankees during their buy-every-available-player era and as a result, he was a casualty of impatience.  Today, he is a valued member of the Los Angeles Dodgers starting rotation and has established himself as a satisfactory pitcher in the major leagues.  Weaver was traded by the Yankees to the Los Angeles Dodgers following the World Series, and since then has also spent time with the Los Angeles Angels, St. Louis Cardinals (with whom he won a World Series in 2006) and Seattle Mariners.  Today, he is a free agent and looking for a team as he has still not “found” himself as a pitcher.  That being said, one cannot help but wonder what would have happened had George Steinbrenner had a little faith in one Theodore Roosevelt Lilly.