Hard as it is to believe, there were times when the Pittsburgh Pirates made shrewd trades to improve their fortunes. While current Pirates general manager Ben Cherington continues to approach offseason moves with the urgency of a man trying to escape from the arms of Sydney Sweeney, we present this subjective, unscientific, yet meticulously researched look at the top five trades in Pirates history. Here they are, in descending order, just like David Letterman used to do it.
Pirates Best Trades Led to Titles
5. Pirates Get the Quail
May 17, 1956: Pirates trade Bobby Del Greco and Dick Littlefield to St. Louis Cardinals for Bill Virdon. The left-handed-batting center fielder Virdon was the National League Rookie of the Year with the Cardinals in 1955 when he hit .281/.322/.433, 17 HR, and 68 RBI. However, he got off to a slow start the next year, hitting just .211/.269/.324 at the time of the trade. Del Greco, a native of Pittsburgh’s Hill District, hit .217/.301/.279 in 1952, his only previous season in the majors. He was off to a slow start in 1956 as well. But he hit two home runs on May 13 in cavernous Forbes Field against the Philadelphia Phillies with Cardinals GM Frank Lane in attendance. According to legend, although that performance raised Del Greco’s average to a paltry .176, it convinced Lane he had to have the seldom-used Italian center fielder.
Hence the genesis of one of the most important trades in Pirates lore. The hasty deal also netted Lane the 30-year-old journeyman left-handed pitcher Littlefield. St. Louis fans hated the trade. They weren’t wrong.
“He’s Kept Our Pitchers in the Majors”
Pirates manager Bobby Bragan coveted a speedy, left-handed hitting outfielder, and Virdon was all that. Virdon was the Pirates leadoff hitter and center fielder through 1965, hitting .266/.316/.375 in a Pittsburgh uniform, including three at-bats when he was reactivated briefly in 1968. He was a strong defensive outfielder, responsible for 51 Fielding Runs Above Average (FRAA) and 100 assists for his career. Virdon won a Gold Glove Award in 1962, but it was 1961 when he led the NL in “range factor,” according to stats guru Bill James.
Nicknamed “the Quail,” Virdon was a key part of the 1960 World Series champion Pirates. By that time, Del Greco was no longer a Cardinal, and Littlefield was out of baseball. Virdon hit .264/.326/.406 in the regular season and saved Game 4 by robbing the New York Yankees’ Bob Cerv of a sure two-run double. No less an authority on outfield play than Roberto Clemente once told The Sporting News that Virdon was “underrated.” “He’s kept our pitchers in the majors with his glove and hitting,” said the great Clemente.
4. “Mad Dog” Saves the Season
June 28, 1979: Pirates trade Fred Breining, Al Holland, and Ed Whitson to San Francisco Giants for Bill Madlock, Lenny Randle, and Dave Roberts. The Pirates finished second to the Phillies in the NL East Division each year from 1976-78. On June 27, 1979, they were 36-32, a game ahead of the Phillies. Unfortunately, the Pirates were still in second place, tied with the Chicago Cubs and looking up at the Montreal Expos. They were one right-handed bat short of a division, and ultimately a World Series, title.
That problem was solved when GM Hardy Peterson traded for Madlock. The headline in the June 29, 1979 edition of The Pittsburgh Press asked, “How Did Peterson Swindle the Giants?” Indeed, “swindle” was the right word. Madlock was already a two-time batting champion at age 28. But he was causing problems in San Francisco and practically forced the trade. Roberts gave the Bucs a second left-handed reliever they sorely needed. Randle, who died recently, was quickly sold off to the Yankees.
Missing Pieces
After the deal, the Pirates went 62-32 and won the World Series. Hitting sixth in the order, where he had RBI opportunities while setting the table for the bottom of the order with his speed, Madlock hit .328/.390/.469, 7 HR, and 44 RBI while stealing 21 bases for the 1979 Pirates. He also hit .375 (9-for-24) in the Series.
Roberts was 5-2 with a 3.26 ERA and 1.526 WHIP in 21 games, 18 of which were in relief. His biggest contribution was his courageous performance on August 25 when he was the winning pitcher in a 19-inning contest in San Diego. The pitchers surrendered by Peterson had nice major-league careers but were expendable. Whitson became best known for a 1985 barroom brawl with manager Billy Martin while with the Yankees.
Madlock gave the Pirates four more good seasons, winning batting titles in 1981 and 1983 and being named to the All-Star Game each year during 1981-83. Unfortunately, he tarnished his Pirates legacy by appearing to give up on the team in 1984. Still, getting a world championship and two batting titles out of the deal makes this one of the greatest trades the Pirates ever made.
3. No April Fools Joke
April 1, 1987: Pirates trade Tony Peña to Cardinals for Andy Van Slyke, Mike LaValliere, and Mike Dunne. “A wonderful deal . . . for Cards’ fans,” read the headline of Bruce Keidan’s April 2, 1987 column in the Pittsburgh Post-Gazette. Wrote Keidan, “Mr. Peña cried when he was informed of the transaction, and so should we. Because this is a trade that strips the Pirates of any vestige of competitive credibility. Sorely in need of starting pitching, a first-rate shortstop and a right-handed power hitter, the Pirates conspired to give away an All-Star catcher without obtaining any of the three.” In the same edition, Pirates pitcher Don Robinson told beat reporter Paul Meyer, “I think it’s a good trade.” When asked why, Robinson replied, “Well, I don’t know why.”
Indeed, at first, it seemed like a bad April Fools joke. Peña was the Pirates’ most popular player at the time, a lone bright spot over a dismal stretch of baseball from 1984-86. Van Slyke and LaValliere were left-handed hitters, and the Pirates were already overly balanced to the left side of the batter’s box. The Pirates were deep in outfielders with Barry Bonds, Bobby Bonilla, Mike Diaz, and R.J. Reynolds. Moreover, the Pirates provided an important piece to an East Division rival that won the NL pennant in 1985.
“Raisin’ the Dead”
Before long, the critics would be eating their words. This was one of many trades GM Syd Thrift made for the Pirates when he turned the franchise’s fortunes around. (The Foghorn Leghorn-ish GM once proclaimed immodestly, “It ain’t easy raisin’ the dead.”) Peña was part of another pennant-winning Cardinals team in 1987. But he was no longer with St. Louis by the time Van Slyke and LaValliere were important catalysts for three straight Pirates division champions from 1990-92.
In eight years as a Pirate, Van Slyke hit .283/.353/.458, 117 HR, and 564 RBI. He was a three-time All-Star and five-time Gold Glove winner in center field. In the outfield, he was credited with 24 FRAA and 107 assists. LaValliere hit a solid .278/.363/.351 in his seven years as a Pirate, winning a Gold Glove Award in 1987, when he led NL catchers with 15 FRAA and a 45.2 caught-stealing percentage. Dunne, a right-handed starting pitcher, was 13-6 with a 3.03 ERA and 1.292 WHIP in 1987, when he was runner-up NL Rookie of the Year. His career went south in a hurry after that.
Mike LaValliere had a .364 OBP between 1987-1992. pic.twitter.com/vHPnr7O1oD
— Stirrups Now! (@uniformcritic) October 16, 2024
2. The Original One
January 30, 1959: Pirates trade Frank Thomas, Whammy Douglas, Jim Pendleton, and John Powers to Cincinnati Reds for Smoky Burgess, Harvey Haddix, and Don Hoak. This trade was reported in big, bold headlines in the next morning’s Post-Gazette. No Pirates trade rocked Pittsburgh in a similar fashion since they traded Ralph Kiner in 1953. Thomas, a Pittsburgh native and right-handed-hitting slugger who once considered the priesthood, hit .275/.333/.474, 163 HR, and 562 RBI in seven-plus seasons with Pittsburgh. Plus, he was popular with the fans. However, Pirates GM Joe L. Brown and manager Danny Murtaugh had grown weary of his poor defense, first in the outfield and later when he was moved to third base.
There may have been another unspoken reason. Thomas was known as an “agitator,” a guy who liked to rib his teammates but never knew when he was crossing a line. That aspect of his personality was exposed to the public in 1965 with a famous altercation with Dick Allen when both were Phillies. Thomas could rub people who didn’t know him well the wrong way. (I believe it was 2009 when I was given the job of chaperoning Thomas to his place at the annual celebration of Game 7 of the 1960 World Series at what remains of the Forbes Field outfield wall. I found him to be loud and brash and opinionated and delightful. When I introduced myself, the first thing he said was, “I don’t care what anybody says. The players in my day were better than the players today.” He signed autographs as “The Original One.”)
Frank Thomas’s distinctive autograph (Photo Credit: Joe Landolina)
“This Clinches the Pennant”
At the time of the trade, Thomas was in Bavaria, Germany, touring United States Army installations as part of a baseball clinic. News of the trade reached his wife first. Then there was a phone call from former Pirate and current Reds pitcher Bob Purkey. “This clinches the pennant for us, Dolores,” said Purkey. He was partially right. The Reds would win the NL pennant – in 1961. By then, Thomas was a Cub.
Meanwhile, the Pirates won the World Series in 1960, with Burgess, Haddix, and Hoak as key figures. Haddix gave them the left-handed pitcher they needed to balance the rotation. Although he was just 45-38 in five years with Pittsburgh, Haddix was the winning pitcher in Games 5 and 7 of the Series. Burgess, a left-handed hitting catcher who was used on a platoon basis, hit .296/.352/.445 in six years as a Pirate. The scrappy Hoak was formerly an amateur boxer and a Marine and started in Game 7 of the 1955 World Series for the victorious Brooklyn Dodgers in place of Jackie Robinson. He became the heart and soul of the club and gave them the solid defense Murtaugh sought at third base. His offense – .281/.364/.415 in four years – was a bonus.
The other players going to the Reds were negligible. Douglas, a one-eyed pitcher, never pitched for the Reds. Outfielders Pendleton and Powers lasted just one year in Cincinnati. Of all the trades Brown made for the Pirates, this was his masterstroke.
1. A Wonderful Conflict of Interest
December 8, 1899: Pirates trade Jack Chesbro, George Fox, Art Madison, John O’Brien, and $25,000 to Louisville Colonels for Honus Wagner, Fred Clarke, Tommy Leach, Deacon Phillippe, Rube Waddell, Bert Cunningham, Patsy Flaherty, Mike Kelley, Tacks Latimer, Tom Messitt, Claude Ritchey, Jack Wadsworth, and Charles Zimmer. Barney Dreyfuss purchased the Colonels in 1899. After that season, the NL determined that it should contract from 12 teams to eight, with the Colonels being rumored to be one of those teams. Dreyfuss desired to stay in baseball. The many talented players he had under contract made him desirable to other teams. He purchased a 50 percent interest in the Pirates with the December 8 trade as part of the deal.
Greatest Trade in Baseball History?
Shortstop Wagner, an eight-time batting champion, was an inaugural member of the Baseball Hall of Fame. Left fielder/manager Clarke is one of two Hall of Fame members who belong there as either a player or a manager. (The other is Frank Chance.) Wahoo Sam Crawford called the speedy Leach “a beautiful ballplayer to watch” in Lawrence Ritter’s book, The Glory of Their Times. In 1902, Leach, a third baseman who later played center field, led the NL with 22 triples and six home runs, all of which are believed to have been of the inside-the-park variety. Pitcher Waddell is also in the Hall of Fame, although it’s Phillippe who holds many of the Pirates’ team pitching records.
Meanwhile, of the players the Pirates surrendered, only Chesbro was more than a marginal player. When Louisville was contracted, Chesbro returned to the Pirates. This group won the NL pennant in 1901-03 and the World Series in 1909. This, of course, was an era where Chance’s Cubs and John McGraw’s New York Giants also reigned supreme. This had to have been one of the best trades in the history of baseball, not just the Pirates.
Main Photo Credit: © Charles LeClaire-Imagn Images
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