Yankees: The worst trades in franchise history

There is a long and storied history behind the New York Yankees franchise. Countless players have come and gone over that time through trades. These are the 15 worst Yankees trades in franchise history, each an instance where hindsight suggests the Yankees were fools. 

Pick any year in Yankees history and you’ll find a host of famous and familiar names up and down the roster. Some were homegrown, players the club scouted, signed, and developed on their own. Some were brought in as free agents, signed to lucrative contracts largely powered by being one of the richest clubs in all sports. Some came to wear pinstripes via trades.

Not every trade worked out in New York’s favor, however.

Sometimes the club acquired the wrong player. Sometimes the mistake came in who they gave up. Context is always a factor, but ultimately it is really the power of hindsight that makes a deal look like a poor one.

15. July 13, 1987. New York trades Bob Tewksbury, Rich Scheid, and Dean Wilkins to the Chicago Cubs for Steve Trout.

Steve Trout (no relation to Mike) was having a fine start to the 1987 season. He was 6-3 through 11 starts, with a trio of complete games. His 3.00 ERA through 75 innings was well ahead of the National League average. Trout’s 1.320 WHIP was the best mark of his career.

Things fell apart quickly after Trout joined the Yankees, however. He’d make nine starts for the club before shifting to the bullpen. He’d only throw 46.1 innings over the remainder of the season, posting an 0-4 record and 6.60 ERA.

New York let Trout leave as a free agent following the season. He’d land in Seattle where he’d struggle through two more seasons before calling it a career.

Neither Scheid nor Wilkins (both former second-round draft picks by New York) produced much in their careers. Scheid would have brief stints in the majors with Houston in 1992 and the Marlins in 1994 and 1995. His career totaled just 54.1 innings. Wilkins threw a total of 31 innings for the Cubs between 1989 and 1991. Bob Tewksbury was the big piece the Yankees would regret moving.

The right-hander had gone 9-5 with a 3.31 ERA in 1986, his rookie season. He struggled to begin 1987 though, posting a 1-4 mark and 6.75 ERA through six starts and a pair of relief appearances. Once he arrived in Chicago, the rough season continued and he found himself back in the minor leagues.

Tewksbury’s career would rebound. He’d pitch through the 1998 season, finishing with 110 wins and a career 3.92 ERA.

14. December 9, 1941. New York trades Tommy Holmes to the Boston Braves for a pair of players to be named later (Buddy Hassett and Gene Moore).

New York had signed Tommy Holmes as an amateur free agent before the 1937 season. While minor league statistics for the late ’30s and early ’40s are somewhat incomplete, Holmes was a solid contributor over his five seasons in the minors. He regularly hit over .300 with 25+ doubles. There was just no room for him in the Yankees outfield, so the team would trade him before he’d make his debut.

He blossomed once arriving in the majors in 1942. After that, he’d become a fixture in the Braves lineup. Holmes was a .302/.366/.432 hitter over his career. He twice led the league in hits and received MVP consideration for four straight years (a strong argument could be made that he should have won it in 1945).

Hassett was at the tail end of his career, playing just one season in New York before retiring. He hit well in that time, at least, batting .282/.325/.364 in 581 plate appearances.

Moore never would play for the Yankees, as his contract was purchased by the Brooklyn Dodgers just three weeks later.

13. March 26, 2013. New York trades Exicardo Cavones and Kramer Sneed to the Los Angeles Angels for Vernon Wells.

For years the Yankees had to deal with Vernon Wells batting in the heart of the Blue Jays lineup. He was a .279/.330/.478 hitter from 2002 to 2010, averaging 36 doubles and 25 homers a year. He never once struck out 100 times in a season. He was a particular thorn in the Yankees side, batting .301/.352/.516 against the team.

Wells earned the massive contract extension the Blue Jays gave him, but changes in the team’s long-term plans eventually necessitated his trade to Los Angeles. Two dismal seasons later the Angels were looking to get out of what remained on that contract — two years and $42 million — and the Yankees came calling.

Wells hit just .233/.282/.349 in his lone season in New York. The team would release him at year’s end, simply swallowing what remained on his contract.

Neither Cavones nor Sneed ever reached the upper minor leagues.

12. December 13, 2003. New York trades Jeff Weaver, Yhency Brazoban, Brandon Weeden, and cash considerations to the Los Angeles Dodgers for Kevin Brown.

Kevin Brown had enjoyed a solid career up to this point. A perennial Cy Young Award contender, Brown had won 197 games with a 3.16 ERA in over 3,000 career innings. The veteran was a workhorse and multi-time All-Star.

New York wanted to add a veteran to their rotation before the 2004 season. Brown, entering his age-39 season, certainly met the veteran label but he was unable to produce in pinstripes.

Brown made 35 starts over the next two seasons in New York, pitching a total of 205.1 innings. His 4.95 ERA and 1.427 WHIP were his worst marks at any stop throughout his career. Brown would retire following the 2005 season.

Weeden spent two years in the minor leagues with Los Angeles and another with Kansas City before leaving baseball to play football (first at Oklahoma State before spending parts of five seasons in the NFL). He was really a non-factor here.

Brazoban was a key piece of the Dodgers bullpen in 2004 and 2005, appearing in 105 games. He’d post a 4.44 ERA and save 21 games before injuries would ruin his career.

Jeff Weaver’s inclusion in the trade was in part so that the Yankees could get out of his contract, which was set to pay him more than $15 million over the next two seasons. Even for a franchise with deep pockets, the production Weaver had provided so far in New York wasn’t matching that cost (more on this later). Weaver proved to be the workhorse that New York thought Brown would be, however. He’d throw 444 innings over those two seasons, going 27-12 with a 4.11 ERA. It was arguably the best two-year stretch of his career.

11. July 31, 2010. New York trades Mark Melancon and Jimmy Paredes to the Houston Astros for Lance Berkman.

Even with a two-game lead in the division and the best overall record in the American League, the Yankees were still looking to add some help on offense with the 2010 deadline approaching. Lance Berkman seemed like an ideal fit — a switch-hitting, high-contact veteran who could provide depth in the outfield and at first base.

Berkman had been enjoying a solid but not spectacular season with Houston prior to the trade. He had 13 home runs and 16 doubles, he’d walked 60 times, and he was posting a .245/.372/.436 slash. While those numbers were below his career averages, they were still strong enough that most viewed the acquisition as a positive one for New York.

Berkman hit .255/.358/.349 over the remainder of the season, with just a single home run in 123 plate appearances. Berkman did homer in the postseason, hitting a game-turning two-run shot in the 7th inning of Game 2 of the Division Series against the Twins. The Yankees would let him leave as a free agent after the season. He would sign with the St. Louis Cardinals and finish seventh in NL MVP voting.

Paredes spent parts of six seasons as a journeyman after the deal, spending time with Houston and four other clubs.

Mark Melancon was once viewed as a potential heir apparent to Mariano Rivera in New York. He’d blossom into a solid closer, but it wouldn’t come for the Yankees. He’d post good numbers for the Astros following the trade — going 10-4 with 20 saves and a 2.85 ERA over a season and a half — and has been traded a number of times since. He’s saved 194 games so far in his career.

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.

8. December 22, 2009. New York trades Melky Cabrera, Mike Dunn, Arodys Vizcaino, and cash considerations to the Atlanta Braves for Javier Vazquez and Boone Logan.

The Yankees were eager to add to their roster with the goal of winning again in 2009. Pitching wasn’t really an area the team needed to address, but once again they found themselves eager to add an arm when the opportunity presented itself. The Braves were suddenly flush with starting pitching after signing Tim Hudson as a free agent. The two teams were easy trade partners.

Javier Vazquez had just finished a career-best year. He won 15 games, posted a 2.87 ERA, and was second the NL in strikeouts. He’d finish fourth in Cy Young voting. On paper, he looked like a nice addition to the Yankees rotation.

Vazquez failed to produce in New York, however. He went 10-10 with an ERA that ballooned to 5.32. Nearly every peripheral statistic took a step back from the season prior. The Yankees let him walk via free agency after the season.

You would think the Yankees had learned their lesson when it comes to Vazquez, but this was actually the second time he was acquired by New York (more on the other trade later).

Logan proved useful for the Yankees, serving as a left-handed option in the bullpen for four seasons, posting a 3.38 ERA in 256 appearances.

Cabrera was the key piece New York gave up, but he’d become somewhat expendable with Brett Gardner’s emergence. Dunn and Vizcaino played pivotal roles for the Braves bullpen over the coming seasons.

7. July 31, 2004. New York trades Jose Contreras and cash considerations to the Chicago White Sox for Esteban Loaiza.

In 2003, Esteban Loaiza won 21 games with a 2.90 ERA en route to finishing second in the AL Cy Young voting. The following summer he’d won nine games already by late July, albeit with peripheral numbers (namely his ERA, WHIP, and K/9) that had been far worse than what he’d done the season before. The Yankees sat 8.5 games ahead in the AL East at the trade deadline but still insisted on adding another starting pitcher.

Loaiza made just six starts for New York before landing in the bullpen, posting an 8.50 ERA and 2.055 WHIP over 42.1 innings of work. Letting him leave via free agency after the season was an easy decision.

Jose Contreras, meanwhile, became a reliable piece of the White Sox rotation. He’d win 15 games in 2005 and helped the club win the World Series. The following year brought about his lone All-Star appearance. Overall he’d throw 900 innings for Chicago over six seasons with a 4.66 ERA. The Yankees gave up on him just a year and a half after signing him out of Cuba.

6. November 26, 1986. New York trades Doug Drabek, Logan Easley, and Brian Fisher to the Pittsburgh Pirates for Pat Clements, Cecilio Guante, and Rick Rhoden.

There was a common thread among many of the Yankees trades in the 1980s. The franchise wasn’t having difficulties on the offensive side of things, but they were constantly looking to add starting pitching (a theme that has resurfaced in other decades since). More often than not those trades failed to work out. Former Yanks Go Yard writer Billy Brost summed it up pretty well a few years ago, “some of the generation’s best players were practically given away for stop-gap measures, and quick fixes that rarely, if ever, worked to the Yankees advantage.”

Doug Drabek was one of those players. The right-hander had a serviceable rookie season for the Yankees in 1986, going 7-8 with a 4.10 ERA. Following the season, however, it seemed the Yankees were dead-set on moving him and there were multiple teams in pursuit (a separate trade weeks later with the White Sox was made which Murray Chass described in the New York Times as a “substitute for the deal in which the Yankees were supposed to give the White Sox Drabek”).

Drabek flourished with the Pirates. He won 15 games in 1988. He took home the NL Cy Young Award in 1990, going 22-6 with a 2.76 ERA. He was a key piece in the Pirates run of division titles in the early 90s.

Easley had two stints in the Pirates bullpen. Fisher spent two years in their rotation.

Clements spent two disappointing seasons in the Yankees bullpen. Guante’s tenure wasn’t much better, but at least put up strong enough numbers over the first half of the 1988 season that the Yankees could trade him to Texas.

Rick Rhoden was useful for New York in the two seasons he spent there. He won 16 games his first season with the team and 12 more the year after. After the 1989 season, he was done with baseball.

5. December 6, 2003. New York trades Nick Johnson, Randy Choate, and Juan Rivera to the Montreal Expos for Javier Vazquez.

Having watched the rival Red Sox add Curt Schilling just days earlier, the Yankees felt the need to respond with a pitching addition of their own. It wouldn’t be the first or last time one of these two teams made a move in response to the other.

Vazquez was coming off a string of successful seasons in Montreal in which he averaged over 200 innings pitched. While not a flashy addition like Schilling, he seemed like a quality pickup. While the results in New York weren’t quite the same as what some expected, Vazquez was at least somewhat useful in his first season in the Bronx.

He’d go 14-10 on the year, posting a 4.91 ERA. Vazquez made the All-Star team with a strong first half, but at season’s end the Yankees would move on from him — using him as part of the package to bring in Randy Johnson from Arizona.

Nick Johnson had just hit .284/.422/.472 the prior season. The contact-hitting first baseman had become a fan favorite in New York. He’d continue to get on base consistently for the Expos and Nationals before injuries shortened his career.

Rivera flashed some power, hitting 132 home runs over his 12-year career. Choate, meanwhile, spent another eleven years in the majors after the trade.

4. February 1, 1999. New York trades Mike Lowell to the Florida Marlins for Ed Yarnall, Mark Johnson, and Todd Noel.

Before the 1998 season, the Yankees signed Scott Brosius to a free-agent deal. He responded quickly, posting a .300/.371/.472 line in his first season in New York. The acquisition left just 15 September plate appearances for the team’s top third base prospect. That offseason they’d trade Mike Lowell to the Marlins.

Lowell spent the next twelve years between the Marlins and the Red Sox, batting a combined .279/.342/.464 with 223 home runs. He made multiple All-Star games, won a Gold Glove, was considered a clubhouse leader, and helped the Marlins beat the Yankees in the 2007 World Series.

None of the three players New York received produced much in their careers. Noel never played above High-A ball. Johnson had only a brief cup of coffee with the Tigers.

Ed Yarnall at least suited up in pinstripes, but his MLB career lasted just 20 innings.

3. July 21, 1988. New York trades Jay Buhner, Rick Balabon, and a PTBNL (Troy Evers) to the Seattle Mariners for Ken Phelps.

Jay Buhner is widely remembered for three things: his bald head, his power-hitting abilities, and for his inclusion in a trade that seemed so bad it found its way into an episode of Seinfeld a few years after the move (Frank Costanza loses it and yells at George Steinbrenner).

Frank was right.

Buhner logged all of 99 plate appearances for New York before the trade. He didn’t hit much in that stretch, batting .198/.253/.319 with just three home runs, but he most definitely turned things around after the move.

Buhner became a fixture in the Mariners lineup over the next 14 seasons. He hit in the heart of their lineup, was a leader in their clubhouse, and became a fan-favorite. The trade is often characterized as one of the best in Mariners history. Buhner hit .255/.360/.494 during his tenure in Seattle, adding another 304 home runs (including hitting 40+ in three straight years from ’95 to ’97) to his resume.

Neither Balabon nor Evers would reach the majors.

Phelps, meanwhile, hit just .240/.339/.442 during his time in New York. He’d get just 342 plate appearances before being traded to Oakland midway through the 1989 season for a minor leaguer (Scott Holcomb).