Pirates deal Clay Holmes to Yankees: Four times the Bucs got the best of the Bombers in a deal

By Joe Smeltzer

The Yankees are winners. The Pirates are losers. The Yankees are rich. The Pirates are poor. The Yankees eat steak. The Pirates eat fast food. The Yankees are Kendall Jenner. The Pirates are Ms. Gulch from The Wizard of Oz. 

This is the narrative, and, for the most part, it’s an accurate perception. Yet, for reasons even more inexplicable than the Buccos beating the Bombers in the 1960 World Series despite being outscored 55-27, the Pirates seem to always have their way with the Yankees whenever the two teams make a trade. 

OK, maybe the Bucs don’t always have their way. The Willie Randolph (borderline Hall of Famer) for Doc Medich (Pirate for a year) deal didn’t work out in Pittsburgh’s favor. The Craig Wilson for Shawn Chacon swap didn’t have much of an impact on anything, and the Eric Hacker for Romulo Sanchez transaction, well, who are those guys? 

Nonetheless, the Pirates know how to get the best of the Yankees in trades, and anybody who needed a reminder of that got one yesterday when the Buccos sent mediocre reliever Clay Holmes to the Bronx for two promising prospects in Hoy Park and Diego Castillo. We will wait and see how this plays out, but the early prognosis is good. Park leads AAA East in hitting, and Castillo has shown promise in AA.

While we await what this deal will look like down the road, here’s a look at some Pirates-Yankees deals of yesteryear.

Nov. 26, 1986: Pirates trade Pat Clements, Cecilio Guante and Rick Rhoden to New York for Logan Easley, Brian Fisher and Doug Drabek

Any Pirates fan should know the two headliners of this six-player deal.

Before 1987, Rhoden was a bright light in one of the Pirates’ dark ages. He posted a 2.72 ERA in 1984, and won 15 games and made the all-star team in 1986. But Rhoden, coming into his age-34 season, didn’t figure into new general manager Syd Thrift’s plans, so the Pirates sent him to the Big Apple.

Enter, Doug Drabek. A decade younger than Rhoden, Drabek had modest success as a rookie for the Yankees in 1986. Four years later, he won the NL Cy Young Award helping the Pirates to their first of three consecutive division championships. Drabek would play a big part in the next two championships as well, and his popularity was such that, in 2013, more than two decades after he pitched his last game as a Pirate, he was the one who threw out the first pitch before that magical October night against the Reds.

July 26, 2008: Pirates trade Damaso Marte and Xavier Nady to New York for Jose Tabata, Ross Ohlendorf, Daniel McCutchen and Jeff Karstens

At one point, it looked like this transaction might go down as one of the best in Pirates history. It didn’t turn out that way.

The number of players the Pirates got in return, however, still made this deal a productive one, as all four players made it to the majors and had at least moderate success.

Tabata never developed into the superstar that we were hoping for but still played five and 1/2 seasons in Pittsburgh and was a key depth piece on three consecutive playoff teams, stepping up in a big way when Starling Marte went on the disabled list late in 2013.

Ohlendorf and Karstens both became fixtures in the starting rotation in the early 2010s, with the former being arguably the Pirates’ best starting pitcher in 2010 (despite going 1-11) and the latter having his best season in 2011, ranking amongst the league leaders in ERA all the way into late July.

McCutchen is the least notable of the four but was still a horse in the Bucco bullpen in that 2011 season, the summer where the Pirates got a taste of success again. He’s best known for his performance in the 19-inning “Jerry Meals game.”

So, although none of the four players the Pirates got for Nady and Marte became a world-beater, considering Nady only played 66 games with the Bombers, and Marte posted a 9.45 ERA out of the bullpen in his only full season in New York, the Pirates still won the trade.

Feb. 18, 2012: Pirates trade Exicardo Cayones and Diego Moreno to New York for A.J. Burnett

Two weeks after the Pirates acquired Burnett, he bunted a ball into his eye, broke his orbital bone and missed two months because of it. At this point, it looked like the Yankees might have won the round.

But Burnett made his Pirates debut in May, became their best pitcher in 2012 and was a big part of the 2013 and ’15 playoff teams before retiring after the 2015 season.

On the Yankees’ end, Cayones never made it to “The Show”, and Moreno only pitched in nine games– four of them for New York.

Burnett’s production, as well as his “I’m-gonna-kick-your-butt” attitude, made him a beloved sports figure in this city, and there’s no question that No. 34 was a central figure in turning the Pirates into winners for the first time in two decades.

Jan. 24, 2021: Pirates trade Jameson Taillon to New York for Miguel Yajure, Roansy Contreras, Maikol Escotto and Canaan Smith

The first of two Bucco-Yankee trades of the Ben Cherington era looks like it could be a Pirate raid.

None of the four prospects the Pirates got in return for post-Tommy John (2.0 nonetheless) Taillon have established themselves as major leaguers, so we don’t know what the full fallout of this deal will be. But Yajure has shown promise in his two starts with the Pirates, and Contreras has worked his way into MLB’s top 100 prospects. Taillon, meanwhile, is struggling in the Bronx.

The Pirates have clearly had some success in making trades with baseball’s flagship franchise. Hopefully, the Clay Holmes deal is another example of the Pirates getting the best of the Yankees in something.

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