The Dodgers and the Yankees had one of the great old-school rivalries in the first half of the 20th century, and thus were reluctant to trade for most of their histories. The teams actually haven’t swapped very many impact players over the past 91 years. The two teams only traded once between 1969 and 1996 before a flurry of trades in the 21st century. But by the time Kevin Brown suffered a self-inflicted fracture of his hand and then got shelled in the playoffs, the worst trade on this list was sealed up.
November 26, 1962: The Yankees trade Bill Skowron to the Dodgers for Stan Williams.
After the 1962 season, the World Series champion Yankees started to get younger. They traded their longtime infielder Skowron to the Dodgers for 25-year-old starting pitcher Stan Williams. Skowron’s excellent Yankee career had run its course and general manager Roy Hamey capitalized on Skowron’s solid ‘62 season to net the talented young hurler. In 1963, Williams worked his way into a consistent role, giving the Yankees 146 innings of 3.21 ERA ball in the rotation and occasionally the ‘pen as New York won their fourth consecutive AL pennant. He followed that up with 82 innings and a 3.84 ERA in 1964, another season of World Series play for the Bombers.
Skowron’s Dodgers would end up emerging victorious over the Yankees in the ‘63 World Series, so the Dodgers would probably say they had no regrets about this deal, but Skowron hit just .203 that year, the lowest mark of his career. The Dodgers flipped him after just the one season for next to nothing. Maybe not the most spectacular win, but the teams have traded sparingly, so this makes the grade.
December 13, 2003: The Yankees trade Brandon Weeden, Yhency Brazoban, Jeff Weaver and $2.6 million to the Dodgers for Kevin Brown.
Weaver was an unspectacular presence in the back of the Yankees rotation and they wanted more, flipping him, Weeden, Brazoban, and cash for Brown. Weaver then gave the Dodgers a combined 444 innings pitched in ‘04 and ‘05, racking up 6.7 fWAR in two seasons. He carried value for his durability alone, and though he maintained only decent performance, Weaver was the all-important innings eater who filled out a rotation and eased stress on the bullpen. Brazoban pitched well for the Dodgers in 2004 as well.
Brown’s career cumulatively was illustrious: 476 starts, 3.28 ERA, 76.5 fWAR, six-time All-Star, a no-hitter to his name. 2003 was one of his finest seasons, and the Yankees thought they’d be getting a renaissance. Unfortunately, his tenure in the Bronx was an unabated disaster from every angle. Rumors of PEDs followed him and only increased when his name popped up in the Mitchell Report after his career ended. Brown was beleaguered by both injuries and an attitude problem before the trade was even made, not to mention he was entering his age-39 season. This was a man who broke hid hand after punching a wall in frustration. It was bad.
Perhaps most egregiously, Brown melted down in Game 7 of the 2004 ALCS. Somehow, a 39-year-old, been-there-done-that veteran was completely overmatched by the moment when his team needed him most. After five earned runs without escaping the second inning, Brown paved the way for the Red Sox to deliver the most humiliating series defeat in Yankees history. An unsuccessful comeback in 2005 spelled the end of Brown’s career.
And yes, included in the trade was that Brandon Weeden of NFL quarterbacking fame.
Most Overlooked Trade
December 11, 2023: The Yankees trade Trey Sweeney to the Dodgers for Jorbit Vivas and Victor González.
A chunk of talent changed hands in the most recent link-up — just over a month ago, the Yankees traded former first-round pick Sweeney for González and Vivas. I’m betting big on potential payoff here, but I think this trade could shape the makeup of both teams more than we know in this moment. All three players involved have the potential to pop off and become big league regulars.
The move is a win-win for the Yankees; Anthony Volpe has shortstop locked down for hopefully the next decade. His promising rookie season cemented the fact that Sweeney was trade bait, and very enticing bait at that. González showed mettle in the playoffs for the victorious 2020 Dodgers. He followed that up with more solid play, this time over 44 games in 2021, netting González a 119 ERA+ in his first full test. He missed 2022 with tricky arthroscopic elbow surgery and had trouble shaking off the rust in 2023, making him a bit of a buy-low. Overall, he sports a 3.22 ERA in 81.2 innings in his young career. None of us are ready to let go of the beloved Wandy Peralta, but as a lefty with some gas and a heavy sinker, González could be his replacement.
González came over with second baseman Jorbit Vivas, at the time the tenth-ranked prospect in a strong Dodgers farm system. Vivas made the jump to Triple-A in 2023 and didn’t fare well, but he’s much more than a throw-in. Turning a talented but organizationally superfluous prospect like Sweeney into two interesting players is a win in my book. Vivas’ hit tool and pull power is evident:
July 31, 2003: The Yankees trade Robin Ventura to the Dodgers for Bubba Crosby and Scott Proctor
July 31, 2007: The Yankees trade Scott Proctor to the Dodgers for Wilson Betemit
This uncommon swap-then-swap-back struck me as weird in a good way — Proctor was a sneaky valuable piece in the organization from 2004-2007. In 2006, Proctor led MLB in appearances with 83, maintaining a 3.52 ERA in 102.1 innings. Now that’s an impact reliever; Joe Torre made sure of it. Meanwhile, Ventura retired at the end of ‘04, and the man who was acquired to replace him at third won the pennant (among other things).
Proctor’s usage started strong once again in ‘07, pitching in 52 games with a 3.81 ERA before Brian Cashman traded him. Curiously, he went back to his original organization the Dodgers in exchange for Wilson Betemit. Proctor was very good for LA down the stretch, adding 31 more appearances to match the previous year’s mark of 83.
Betemit, meanwhile, was a net negative in the second half of ‘07. He posted a three percent walk rate with the Yankees in ‘08 without much of anything to offset it, and was gone by ‘09. Karmic equivalence — the Yankees got one over on the Dodgers, then vice versa ... a lot like their erstwhile rivalry in the early and mid-20th century. There’s a caveat though, as Betemit was unloaded on the White Sox, who were kind enough to gift-wrap 2009 folk hero Nick Swisher in exchange.
Other Trades of Note
November 30, 1967: The Yankees purchase Gene Michael from the Dodgers.
Both a purchase—which we try to avoid in this series—and one that only led to New York acquiring a light-hitting infielder, but “Stick” Michael would turn out to mean so, so much more for the franchise.
June 20, 2000: The Dodgers trade José Vizcaíno and cash to the Yankees for Jim Leyritz.
After reacquiring him late in 1999, the Yankees decided to flip their old friend Leyritz to LA to get an infielder who could occasionally help bail them out of Chuck Knoblauch’s fielding woes at second. Vizcaíno only had a 67 OPS+ for the Yankees during his brief run in 2000, but he came up huge in October for Game 1 of the Subway Series with a four-hit night and a walk-off winner.
August 2, 2022: The Dodgers trade Clayton Beeter to the Yankees for Joey Gallo.
Oh, Joey. It sure didn’t work out in New York, but at least Beeter is a nice pitching prospect now.