The Yankees and Reds are two of the most historic franchises in all of baseball. While the Yankees obviously lead the way with 27 World Series titles, Cincinnati aren’t slouches themselves, having won five championships. One of those came in 1976, when their “Big Red Machine” knocked off an upstart Yankee team in their first Fall Classic appearance in over a decade. However, the Yankees have beaten the Reds in the postseason twice in 1939 and 1961.
Now, it’s time to take a look at some of another kind of history between the teams. Let’s go back in time and look at some of the most notable trades the Yankees and Reds have made with each other over the years.
November 3, 1992: The Reds traded Joe De Berry and Paul O’Neill to the New York Yankees for Roberto Kelly.
When it initially happened, the Yankees sending Roberto Kelly for the Reds for a different, slightly older outfielder wasn’t the most popular deal. Kelly was homegrown, a recent All-Star, and one of the few bright spots for the late ‘80s/early ‘90s Yankees teams that were still stuck in a malaise. However, the man who made the swap with the Reds, Gene Michael, was pretty good at his job, as it turned out.
While he was coming off a slight down season in 1992, Paul O’Neill had been a very solid major leaguer with the Reds to that point, helping them to a World Series title in 1990. It turned out New York would be the perfect place to unlock the next level for the man who would become known as “The Warrior.”
O’Neill’s lefty swing and on-base ability fit in perfectly in the Yankees’ lineup, as he quickly helped them back to relevance over the 1993-95 seasons, and then was a key middle-of-the-order bat as the team won four World Series titles in five years from 1996-2000.
An added benefit to the deal was that moving Kelly permanently opened up center field for Bernie Williams, who would join O’Neill in the heart of the Yankees’ lineup for years to come.
Kelly had a perfectly commendable MLB career in his own right (even returning to New York for a hot minute in 2000), but the 1990s/2000s Yankee dynasty wouldn’t have been what it was without O’Neill.
January 21, 2019: The New York Yankees traded Sonny Gray and Reiver Sanmartin to the Cincinnati Reds for Shed Long Jr. and 2019 competitive balance round A pick.
For whatever reasons you want to ascribe to it, Sonny Gray’s tenure with the Yankees did not work out. While he was solid down the stretch and in the postseason run in 2017, Gray struggled in 2018, leading to the team deciding to cut their losses. They even admitted so publicly, which did not exactly help his trade value.
In January 2019, the Yankees sent Gray to the Reds for prospect Shed Long Jr., who they traded to the Mariners for prospect Josh Stowers literally minutes later. Stowers was later used in the Rougned Odor trade with the Rangers and has never appeared above Double-A.
Whether it be the way he was coached with the Yankees, his inability to handle New York, or something else, Gray would bounce back after leaving and going to the Reds. With them and the Twins, he’s gotten back to the borderline ace he had been before coming to the Yankees, and inked a three-year deal with the Cardinals earlier this offseason. Maybe he wouldn’t have ever made it work with the Yankees, but he’s certainly been better for his teams than what the Yankees dumped him for.
Most Overlooked Trade
December 14, 1961: The Cincinnati Reds traded Marshall Bridges to the New York Yankees for Jesse Gonder.
Bridges had his ups and downs in a four-year career with the Cardinals and Reds when the Yankees acquired him, looking for bullpen help going into the 1962 season. “Sheriff” ended up being the perfect fit, as he recorded a a 3.14 ERA (121 ERA+) in 71.2 innings, helping the Yankees to the pennant in ‘62. His 18 saves were a team high as the team won the AL and then the World Series over the Giants.
The rest of Bridges’ Yankee career ended up derailed after an incident in a bar during spring training in 1963 led to him getting shot in the leg. He struggled a bit that season, leading to the Yankees selling him to the Washington Senators in November ‘63.
Adding to that, the Yankees only had Gonder, who they sent the other way, thanks to a April 1960 trade when they got him from the Reds to begin with.
July 28, 2021: The Yankees traded Luis Cessa and Justin Wilson to the Reds for a player to be named later. The Reds sent Jason Parker (August 30, 2021) to the New York Yankees to complete the trade.
The Yankees’ 2021 reunion with Justin Wilson was not working out, with the reliever posting a 7.50 ERA in 18 innings. In an effort to dump some salary as they remade the roster at the deadline, the Yankees sent Wilson to the Reds. However, the cost of doing business was that the Yankees also had to give up Cessa, who had finally started to show some promise that year. It’s not as if Cessa or Wilson did anything after the trade to make the Yankees regret the deal, though Parker, who they got back as a throw-in, hasn’t played organized baseball since the conclusion of the 2021 season. The issue was them having to sacrifice a potentially useful player just to cover up a mistake elsewhere.
Adding a layer to the weirdness of this trade was that the Yankees originally got Cessa as part of a trade with the Tigers that sent Wilson to Detroit, the first time the Yankees had Wilson.
Other Trades of Note
December 28, 2015: The Reds trade Aroldis Chapman to the Yankees for Eric Jagielo, Caleb Cotham, Rookie Davis and Tony Renda.
This one was on the shortlist for “best,” if just for the fact that the Yankees were then able to go and trade Chapman at the 2016 deadline to the Cubs for Gleyber Torres and others. However, it does have to be noted that the Yankees were able to get Chapman for such a cut-rate package to begin with as this trade happened right after the domestic violence allegations bubbled up and a possible deal to the Dodgers was nixed. (He would be suspended for the first 30 games of 2016.) Even if you want to just focus on the pure on-field stuff, he was also such a deeply frustrating pitcher to watch, even when he was good.
July 31, 2003: The Yankees trade Brandon Claussen, Charlie Manning, and cash to the Reds for Aaron Boone.
You know the one:
November 4, 1981: The Yankees trade a player to be named later and Brian Ryder to the Reds for Ken Griffey. The Yankees sent Freddie Toliver (December 9, 1981) to the Reds to complete the trade.
The Yankees acquired the elder Griffey from the Reds ahead of a five-year run from 1982-86. He was pretty solid, although his tenure is arguably more known for poisoning the well of Ken Griffey Jr. ever wanting to play in the Bronx.
August 5, 1939: The Reds trade players to be named later and $40,000 to the Yankees for Vince DiMaggio. The Reds sent Frenchy Bordagaray (January 27, 1940) and Nino Bongiovanni (January 27, 1940) to the New York Yankees to complete the trade.
After getting Vince DiMaggio from the Boston Bees (Braves) in February 1939, the Yankees had a second DiMaggio in their organization for a couple months that year. However, the third-best MLB DiMaggio brother, Vince, never joined the best one, Joe, on the Yankees’ major league roster.