15 worst trades in New York Yankees history

The New York Yankees have long been hesitant to trade top prospects for help that can get them over the World Series hump. Perhaps it's because they're ... bad at it?

The unfortunate reality is that, no matter how many Ls you've taken on the trade market, dealing prospects for impact talent is basically always the right way to go -- as long as you've scouted your impact talent properly. The Yankees can't let their recent rear-view mistakes dissuade them from continuing to push towards a title ... but they've still let their issues compound recently, chasing a lopsided deal with another false idol.

Notice how none of these stinkers are from the Yankees' heyday in the '40s, '50s and '60s? Back then, the Yankees seemingly won every trade, from the Don Larsen swap with the Orioles to the Roger Maris plunder to any one of the hundreds of successful deals they pulled off with the Kansas City A's.

Now? The rest of MLB has caught up, and they've figured out the Yankees will -- 9 times out of 10 -- pick the wrong prospects to protect. Exaggerating. Sort of.

Of all the Yankees' big swings, these are the 15 that worked out the worst.

15 Worst New York Yankees Trades of All Time

15. Dec. 13, 2003: Yankees Acquire Kevin Brown('s Contract) for Jeff Weaver, Yhency Brazoban, Brandon Weeden

Immediately after falling to the Yankees in the 1998 World Series, Kevin Brown traded Padres brown for Dodger Blue, signing a free agent contract that helped redefine the pitching market in the years that followed. His seven-year, $105 million deal made him the still-unexpected answer to a trivia question as baseball's first $100 million man.

Fittingly, he spent Years 6 and 7 of that deal with the Yankees after performing quite well in three 200+-inning years with the Dodgers, dominating in a fourth shortened season, and basically losing 2002 to injury.

At the age of 39 in 2004, Brown managed a 10-6 record with a 4.09 ERA in 132 innings. Nearly overnight, he aged out of inducing swings and misses (83 Ks, 132 hits allowed), and poisoned his solid numbers by becoming infamous in pinstripes. He punched a clubhouse wall with his left hand in September, breaking bones down to the wrist, but was able to make it back for the postseason. Kind of a bigger bummer! He finished off the Yankees' 2004 collapse with two horrific starts including a Game 7 clunker, allowing 9 runs in 3.1 innings. He retired after 13 more troubled starts in 2005, making this a bad trade no matter what the Bombers had surrendered.

14. Aug. 1, 2022: Yankees Trade Ken Waldichuk, JP Sears for 8 Frankie Montas Starts

The process was fine here. The Yankees had to go for it at 2022's deadline with a superior team to 2021's bunch, and there was no way they were trading Anthony Volpe for Luis Castillo, who ultimately went to the Mariners.

They also firmly believe they can print top-level pitching whenever they want to these days, and they remain unconcerned about the dearth of depth currently in the upper minors, assuming Will Warren and Drew Thorpe will join Matt Krook soon enough.

No matter how calculated the risk was at the time, though, it hasn't worked out. It has, in fact, bombed spectacularly. The process gets less sound when you recall Montas had a balky shoulder before he was traded, the medical team approved whatever was in there, and then he showed up with a cement mixer and had to be shut down again in September. It gets lowered another level by Montas' career ERA on the road, which sits at an unsightly 4.72. The Yankees believed that trend would reverse itself under their tutelage; Montas never got a chance to learn much.

Look for this trade to move up in next year's edition of this list, creating room for "Hayden Wesneski for Scott Effross."

13. July 13, 1987: Yankees "Go For It" at 1987 Trade Deadline, Trade Bob Tewksbury for Steve Trout

The son of former MLB pitcher Dizzy Trout (petition: MLB needs more Dizzies), Steve was a solid left-hander in the early '80s who helped push the 1984 Cubs to the cusp of the World Series. Flanked by Rick Sutcliffe and Dennis Eckersley, he pitched 8.1 awesome innings in Chicago's Game 2 triumph over the Padres, but the Cubbies were unable to close out the series, and Trout was left to chase rings elsewhere.

By July 1987, Trout was midway through a heater with the Cubs, pitching back-to-back complete game shutouts in Chicago immediately before being dealt to the Bombers to solidify their staff for a potential playoff run led by MVP candidate Don Mattingly. Unfortunately, Trout succumbed to Ed Whitson Disease after joining the Bombers and busted immediately, walking 37 men in 46.1 innings and posting a 6.60 ERA. He was salary dumped to the Seattle Mariners after the season ended, where he spent two more extremely poor years before retiring.

The prospect they surrendered? The rarely-discussed but extremely solid Bob Tewksbury, who went 110-102 with a 3.92 ERA in his career, but who posted just 10 of those wins with the Yankees before being ding-dong-ditched midway through a tough '87 season. He rebounded, of course, making the All-Star team in 1992.

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12. Dec. 22, 2009: Yankees Acquire Javier Vazquez, Again, for Melky Cabrera/Mike Dunn/Arodys Vizcaino

Fool me once, shame on me. Fool me twice? Well, sh--shame on ... I won't get fooled again!

Five years after dropping him off in Arizona in the Randy Johnson trade after an up-and-down 2004 season that ended in the dumps (we'll get to that later), the Yankees tried to reinforce their repeat chances by sending Melky Cabrera to Atlanta (and opening up a starting role for Brett Gardner) in exchange for Javier Vazquez.

Somehow, it went far worse the second time. Vazquez was eminently hittable in 2010, posting a 5.32 ERA in 157.1 innings and finding himself out of the rotation by crunch time. Naturally, he rebounded with a 3.69 ERA the next season in Florida, his final big-league campaign.

Turns out, the Yankees also acquiring Boone Logan in this deal ended up being the way more impactful move! Probably not good.

11. July 31, 2017: Yankees Acquire Sonny Gray for Jorge Mateo, James Kaprielian, Dustin Fowler

The process was sound! The practice led to 45,000 fans booing a smiling man, teeth gleaming as he left the mound after getting lambasted by the last-place Orioles. Pretty bad practice.

At the very least, if not for Sonny Gray, the Yankees may never have ended up with Matt Blake, instead sitting out the drudgery of the Larry Rothschild Era for a few more seasons.

Gray was the pitching prize of the 2017 trade deadline (well, at least he was before everyone figured out Justin Verlander was also available at the end of the next month), but we probably should've realized this was all going to go sideways when the righty chose "Pickles" as the nickname on the back of his Players Weekend jersey.

The ex-A's starter was serviceable, not great in '17, posting a 3.72 ERA in 11 starts with 59 Ks and 55 hits allowed in 65.1 innings. Revisionist history says he was a disaster from the start, and his five one-hit innings in Game 4 of the ALCS against Houston can't be ignored. Still, the Yankees were hoping for an ace, and they got a No. 3/4.

The next season, things went off the rails. Gray posted a "get me out of here" 4.90 ERA and found himself routinely booed by the unforgiving public; he was dumped to Cincinnati the next offseason. The pieces the Yankees surrendered didn't really sting (Volpe, Peraza > Mateo), but this was still emblematic of another deadline whiff for the impact it was supposed to bring.

10. Feb. 1, 1999: Yankees Dump Mike Lowell to Florida for Todd Noel, Mark Johnson and Ed Yarnall

At the time, the Yankees likely believed in Scott Brosius (smart, coming off 1998 and his World Series MVP campaign) and couldn't envision a role for Mike Lowell (short-sighted).

Instead of continuing to develop their 25-year-old infielder, they shipped Lowell to the Marlins, where he subconsciously vowed revenge. Unsurprisingly, the slugging third baseman went on to sting the Yankees not once, but twice.

In 2003 with Florida, he helped lead the charge to upset the Yanks in the World Series, hitting 32 homers during the regular season and ripping two more in a seven-game NLCS squeaker against the Cubs (though he only hit .217 in the Fall Classic).

And yes, in 2007, he went and got the Red Sox a second World Series in the era, hitting .333 with a homer in the ALCS and .400 with a bomb against the Rockies, earning WS MVP. Boston acquired Lowell in the wildly successful Hanley Ramirez trade that also sent Josh Beckett to Beantown. The Yankees? They turned him into Ed Yarnall.

9. Dec. 4, 2003: Yankees Acquire Javier Vazquez From Expos for Nick Johnson & Co.

The trade that made the 2009-10 Yankees say, "Let's do this all again!"

Vazquez was viewed as the potential missing piece entering the 2004 season, a small-market strikeout artist who'd long been coveted and who could fill in any dominance gaps not already occupied by Kevin Brown. Plenty of teams thought they could save the right-hander from Montreal, Pedro Martinez-style, and they weren't exactly thorough in creating Step 2 of that plan after getting him out.

Somewhat forgotten is the fact that Vazquez made the 2004 All-Star Game in Houston with the Yanks, who dominated the balloting that year, completely unaware of the humiliation yet to come in October. What's remembered is his 4.91 ERA in 198 innings; Vazquez could eat innings, but he couldn't dominate them. And, yes, he walked five in 2.0 innings in Game 7 of the 2004 ALCS, throwing more gas on Brown's fire.

The Yankees really went out and nabbed this guy a second time, too. "He's changed! He loves big buildings and the spotlight now! He does, he promised!" He didn't.

8. March 13, 2022: Yankees Add IKF, Josh Donaldson's Massive Salary for Gary Sánchez, Gio Urshela

The Pros to This Trade: The Yankees' pitching staff is thriving with defense-first All-Star Jose Trevino behind the plate rather than Gary Sánchez, who remains unsigned this offseason. They also probably were eager to move off Gio Urshela (who has since moved onto the Angels), considering their current infield logjam.

The Cons? They added more members to that logjam! Josh Donaldson's immobile salary is now entrenched at third for another season, and Isiah Kiner-Falefa was tendered a contract for $6 million this season despite Oswald Peraza, Anthony Volpe and Oswaldo Cabrera coming up behind him. Plus, the Yankees could've just non-tendered Sánchez instead of attaching him to any package, saving $9 million in the process.

If the Bombers had acted like the Old Yankees here, absorbing Donaldson's fat salary because Minnesota couldn't, then operating normally, that would've been one thing. But they sucked in Donaldson's cash, they played poor. They let his money hamstring them, too. That, plus Donaldson being whomped by the aging curve, turned this poorly-thought-out trade to mush.

7. July 5, 2002: Yankees Trade Ted Lilly, Add Jeff Weaver in Three-Team Whirlwind

Tons of interesting players changed hands in this one! The Yankees received none of them. When the dust settled, the Detroit Tigers had added future rotation stalwart Jeremy Bonderman and eventual '08 Rays masher Carlos Peña, while the Oakland A's had secured eventual All-Star left-hander Ted Lilly. The Yankees? They had Jeff Weaver, whose long, flowing locks never quite fit in in the Bronx.

Weaver, another member of the somehow-never-ending club of pitchers from small-market teams who the Yankees believed had another level to their games, flamed out in the Boogie Down, too. He posted a 4.04 ERA in 15 games post-trade in 2002, but put up a 6.75 ERA in two outings in a five-game ALDS defeat at the hands of the Angels.

2003? Weaver went 7-9 with a 5.99 ERA. Absurdly garish today, but somehow, the Yankees had one of these guys on the staff every season from 2002-2011. He was given one, singular playoff appearance, stepping into the bottom of the 11th of Game 4 of the World Series in Miami. Somehow, Joe Torre got it to work! He retired Jeff Conine, Lowell, and Derek Lee in order to preserve the tie! Wow!

Then, the first batter of the 12th, Alex Gonzalez, walked him off and flipped the series. Can't win 'em all. Lilly, who posted a 4.34 ERA in Oakland that summer and was one year away from his first All-Star appearance, probably wouldn't have done that.

6. Nov. 26, 1986: Yankees Trade Doug Drabek for Pirates Package

We're now entering the "1980s Yankees Pull the Plug on a Prospect Too Quickly" portion of the list, starring future 1990 Cy Young winner Doug Drabek in the No. 6 spot.

Following the '86 season, the Yankees sacrificed Drabek in a package meant to acquire Pirates veteran hurler Rick Rhoden. Rhoden had made the All-Star team and finished fifth in the Cy Young chase in '86, and was actually (clears throat) solid in the Bronx! He went 16-10 with a 3.86 ERA in 1987 with the Bombers, but was unable to overcome Steve Trout's stink, as the team again missed the playoffs. Rhoden was solid again in '88 before being dealt to Houston and finishing his career there in 1989.

Drabek? He leveled up almost immediately in the 'Burgh. The next four seasons were like an incline pyramid:

1987: 11-12, 3.88 ERA, 176.1 innings
1988: 15-7, 3.08 ERA, 219.1 innings
1989: 14-12, 2.80 ERA, 244.1 innings
1990: 22-6, 2.76 ERA, 231.1 innings, Cy Young Award

Honestly? He didn't hit the downward slope until 1995 with the Astros. It would've been very nice for some of the worst teams in Yankee history to have Drabek fronting their rotations during the dead years. Particularly ironic that he got much worse in '95, though, just as the Yankees were ascending. His struggles probably prevented the Yankees from trading for him at that year's deadline and absorbing his late-career implosion.

5. July 28, 2021: Yankees Trade 4 Prospects for Joey Gallo

Why isn't this one rated higher? All four of the prospects sent to Texas were going to be traded or nicked off the 40-man roster to clear room to protect more coveted Yankees. All due respect to Josh Smith and Ezequiel Durán, but neither has shown the type of potential exhibited by Peraza, Volpe or Cabrera. The Yankees were trading from a surplus, and they thought they were filling a need with every stathead's 40-homer-hitting obsession.

However, those in the know always knew Gallo might have trouble adjusting to New York. Brian Cashman didn't listen to those evaluators, supplementing his acquisition of Perfect Fit Anthony Rizzo with one of the worst possible partners.

There may be deeper issues at play than simply letting Gallo rediscover his groove at the plate. Heyman cited a scout who said the Big Apple is a 'challenge' for the two-time All-Star and 'gets in his dome.'

Gallo was almost impossibly bad with the Bombers, hitting 25 homers in 140 combined games across two years, but batting .160 in 2021. "He's not a high-average guy, but he's not that bad," every Yankee fan said prior to 2022 before watching him bat ... .159. The power didn't come as regularly, the whiffs piled up (a ghastly 194 in those 140 games), and every New York trend continued after the deadline in Los Angeles (57 more Ks in 117 at-bats, .162 average).

There will never be a more unpleasant player to watch in Yankees history. At the moment, Gallo's rivaled only by That One Ronald Guzman Game Where He Whiffed, Whiffed, Dribbled Into a Killer Double Play and Didn't Hustle to First.

4. July 31, 2004: Yankees Acquire Esteban Loaiza for Jose Contreras, Cash, Dignity

Long before Loaiza was headed to prison for trafficking cocaine, he was wrecking the 2004 Yankees season from the inside out.

Imagine if those Yankees had simply kept Andy Pettitte instead of trying to "level up" with Brown and Vazquez, then trying to stem the tide with Loaiza at the deadline? I've certainly stayed up all night thinking about this before!

Loaiza broke out with the 2003 White Sox, finishing second in the Cy Young race with a 21-9 record, 2.90 ERA, and a league-leading 207 Ks in 226.1 innings pitched. He was no longer that guy in 2004, but somehow received a courtesy All-Star invite for going 9-5 with a 4.86 ERA at the break.

After the Yankees obtained him in exchange for their own scuffling project in Contreras, he ... oh boy, brace yourselves ... went 1-2 with an 8.50 ERA in 10 games (six starts). Know what you're about to ask: Did he somehow end up being used in the ALCS against the Red Sox anyway? He sure did! He was surprisingly competent, posting a 1.42 ERA in 6.1 innings across two games.

Unfortunately, the single earned run he allowed was a walk-off hit by David Ortiz as the curse drums began to beat louder. Oops! Where's Pettitte when you desperately need him?

3. July 21, 1988: Ken Phelps for Jay Buhner

I got a lot of problems with you people.

Years before George Steinbrenner was on Frank Costanza's couch explaining that his son had likely passed away, while also justifying this deal by saying his people loved Ken Phelps' bat, the Yankees once again believed they were swapping out the right young talent for a veteran leader. Wrong-o.

Buhner certainly prevailed in the Feats of Strength, and Phelps' career was done by 1990. He spent half of both 1988 and 1989 in the Bronx, actually posting an .890 OPS in 35 successful games immediately after the trade. The next season, he slowed down, with a .718 mark in 86 games before he ended up in Oakland and regressed further into retirement.

Phelps' "bat" made noise like Steinbrenner was promised for about 30 games, but Buhner left Big Stein wearing the bucket, hitting 40 homers annually from 1995-1997. He might've been a great addition to some early-90s Yankee teams that were a few pieces away from being truly competitive (1993, for example).

Hey, maybe without this brutal trade, the Yankees ultimately never swap Roberto Kelly for Paul O'Neill, though, a silver lining if there ever was one. Still, Steinbrenner got swindled, much the same way he did when he mistook a burning jacket placed in front of the vent for the smell of delicious calzones.

2. October 21, 1981: Yankees Trade Willie McGee to Cardinals, Nab Absolute Mega-Star Bob Sykes

Willie McGee could've been an '80s Yankee star, directly coming off a 1981 World Series loss that led to George Steinbrenner wreaking havoc.

Imagine the ripple effects if New York keeps him? McGee debuted with the Cardinals in 1982, instantly becoming a star and finishing third in the Rookie of the Year chase. It's not clear what was obscuring George Steinbrenner's vision here. Let's take McGee off the Cards -- do they still go all in on speed in the '80s, leading to a 1982 World Series win and two other NL Championships? Do the Yankees still add Rickey Henderson and get to the Cardinals' blueprint first, putting some elite burners around Mattingly and Dave Winfield?

McGee was one of the preeminent stars of the decade, winning MVP in 1985 and hitting .353 with 10 bombs, 18 triples, and a 147 OPS+. He played until 1999 at the age of 40, still showing out in a part-time role after returning to the Cards. And who'd the Yankees get in return? Bob Sykes, who is technically a living, breathing guy, but never made an MLB appearance again after pitching for the Cards in 1981. Ghastly.