Yankees: The worst trades in franchise history

10. July 5, 2002. New York trades Ted Lilly, Jason Arnold, and John-Ford Griffin to the Oakland Athletics as part of a three-team trade. New York acquires Jeff Weaver from the Detroit Tigers.

For a Yankees team that was regularly looking to add more starting pitching (a common theme in the early 2000s), adding an option like Weaver made some sense on paper. He’d been durable (averaging 210 innings in each of the three prior seasons). He was once again having a decent season in 2002 for the Tigers, going 6-8 with a 3.18 ERA boosted by three shutouts.

Weaver’s tenure in New York didn’t pan out quite as well. He went 5-3 with a 4.04 ERA and found himself pushed to the bullpen before the season ended. The next year wasn’t much better, as he went 7-9 with a 5.99 ERA. After being left off the postseason roster for both the Division and League Championship Series, Weaver allowed a 12-inning walk-off home run to Alex Gonzalez in his lone World Series appearance.

Weaver’s tenure in New York was rough and it played a pivotal role in the club’s decision to trade him away. The deal that brought him to the Yankees merits it’s own discussion, however.

Neither Arnold nor Griffin were impactful for Oakland. Arnold never made it out of the minor leagues. Griffin received a brief cup of coffee, but only after the A’s traded him to Toronto.

Ted Lilly, on the other hand, went on to have a fairly solid career. He won 130 games with a 4.14 ERA over 15 years in the majors, making a pair of All-Star appearances. At the time of the trade, he was pitching just as well as Weaver.

9. August 6, 2003. New York trades Armando Benitez to the Seattle Mariners for Jeff Nelson.

Jeff Nelson was an important cog in the Yankees bullpen throughout their title runs in the late 1990s, averaging 61 appearances a year with a 3.41 ERA from 1996 to 2000. The 6’8″ right-hander wasn’t quite that same pitcher when the team brought him back for another go-around in 2003. He’d only throw 17.2 innings over the latter half of the season before departing once again via free agency.

Just a month before trading him for Nelson, the Yankees added Armando Benitez from the New York Mets. The cost to acquire Benitez wasn’t high, but moving on from him so soon after the acquisition came as a surprise to many. The right-hander made only nine appearances for the Yankees, with a 1.93 ERA. Coming from Flushing he was intimately familiar with pitching in the high-stress environment that New York can be and the move to Queens didn’t seem to faze him.

Benitez went to the Marlins via free agency the following season, where he would save 47 games and post a 1.29 ERA. It is unlikely the Yankees would have been able to re-sign him had they held onto him (he wanted to close and nobody was going to unseat Rivera in that role) but he would have been a nice piece at the back of the bullpen for more than those nine games.