10 biggest trades in Pirates history

December 1st, 2021

PITTSBURGH -- The Pirates' long history of trades runs the gamut from amazing to appalling, from deals that set up World Series champions to swaps that set them back for several seasons. No matter the immediate reaction, most trades wind up falling somewhere in the middle. But everyone remembers the deals that clearly delineate winners and losers.

Here are 10 of the most notable trades in Pirates history -- some wins, some losses.

1. Bucs' best? No foolin'
Pirates got from Cardinals: OF Andy Van Slyke, C Mike LaValliere, RHP Mike Dunne
Pirates gave up: C Tony Pena
Date: April 1, 1987

On April Fools' Day in 1987, the Pirates sent their longtime All-Star catcher to St. Louis for their future center fielder, starting catcher and a useful pitcher. Van Slyke turned into a star (and a popular one, at that), and LaValliere was behind the plate as Pittsburgh won three straight National League East titles from '90-92. The Pirates made a similarly smooth move to swipe starting shortstop Jay Bell from the Indians before the '89 season.

2. Championship building
Pirates got from Reds: LHP Harvey Haddix, C Smoky Burgess, 3B Don Hoak
Pirates gave up: RHP Whammy Douglas, OF Jim Pendleton, OF John Powers, INF/OF Frank Thomas
Date: Jan. 30, 1959

The Pirates gave up Thomas, an All-Star slugger in the mid-1950s, but little else of value. In return, they received three players who factored significantly into their '60 World Series championship. Haddix went 45-38 with a 3.37 ERA in five years with Pittsburgh. (He also made a nearly perfect start you may have heard about.) Burgess, a three-time All-Star, batted .296 in parts of six seasons with the Bucs. Hoak finished second to teammate Dick Groat in the '60 NL MVP Award voting as the Pirates won their first World Series since '25.

3. Bringing in Bobby Bo
Pirates got from White Sox: 3B Bobby Bonilla
Pirates gave up: RHP Jose DeLeon
Date: July 23, 1986

It's not that DeLeon was bad for the White Sox; he was better for them and the Cardinals in the years following the deal than he was for the Bucs from 1983-86. But Bonilla was a force in the batter's box and, like Van Slyke and LaValliere, a critical part of their success in '90-91. Bonilla was a four-time All-Star and three-time Silver Slugger Award winner in Pittsburgh, and he recorded two top-three NL MVP finishes (behind Barry Bonds both times) before signing with the Mets.

4. Cy Young sighting
Pirates got from Yankees: RHP Doug Drabek, RHP Logan Easley, RHP Brian Fisher
Pirates gave up: LHP Pat Clements, RHP Cecilio Guante, RHP Rick Rhoden
Date: Nov. 26, 1986

Another deal that made the Pirates' early '90s run possible. Pittsburgh's list of Cy Young Award winners is remarkably short for such a venerable franchise, but Drabek -- a legitimate ace for the Pirates -- joined Vern Law as the Bucs' second Cy Young as he went 22-6 with a 2.76 ERA in 1990. Overall, Drabek went 92-62 with a 3.02 ERA in 196 starts over six seasons with the Pirates.

5. Giles and Giles
Pirates got from Indians: OF Brian Giles
Pirates gave up: LHP Ricardo Rincon
Date: Nov. 18, 1998
Pirates got from Padres: OF Jason Bay, LHP , LHP Cory Stewart
Pirates gave up: OF Brian Giles
Date: Aug. 26, 2003

The Pirates turned a lefty reliever into one of the franchise's most productive hitters, then swapped him for a package of young talent five years later. Giles hit .308 with a 1.018 OPS in parts of five seasons for Pittsburgh, then put together a number of strong seasons in San Diego. Bay also starred in Pittsburgh, winning NL Rookie of the Year Award honors in 2004 before two more All-Star campaigns. Perez briefly looked like an ace as he posted a 2.98 ERA over 30 starts in '04; he faltered after that, but it was the beginning of an impressively long career.

6. The other Bay trade
Pirates got from Dodgers/Red Sox: 3B Andy LaRoche, RHP Bryan Morris, OF Brandon Moss, RHP Craig Hansen
Pirates gave up: OF Jason Bay
Date: July 31, 2008

This deal wasn't quite so poorly received when it happened, but it's the one Neal Huntington would most like back. It was a massive haul in a three-way deal and, thus, a huge chance to kick-start the Pirates' rebuild under the new regime. However, it went up in flames, with none of the prospects making a significant impact. In subsequent years, the Pirates made significant changes to their scouting and analytics departments that wound up benefiting them during their 2013-15 postseason run.

7. The sell-off
Pirates got from Cubs: RHP Matt Bruback, INF Jose Hernandez, INF Bobby Hill
Pirates gave up: 3B Aramis Ramirez, OF Kenny Lofton, cash
Date: July 23, 2003

The Pirates had to cut payroll, and the mandate cost them a bright young star in Ramirez and the veteran Lofton. Ramirez went on to enjoy a good career -- entirely in the NL Central -- that, oddly enough, ended a few months after another July 23 trade brought him back to Pittsburgh in 2015. The Pirates quickly dumped Bruback and released Hernandez at the end of the season. Hill hit two homers in 185 games for the Bucs. Furthermore, Lofton was excellent for the Cubs down the stretch and played until he was 40 years old.

8. See ya, Schmidt
Pirates got from Giants: OF Armando Rios, RHP Ryan Vogelsong
Pirates gave up: RHP Jason Schmidt, OF John Vander Wal
Date: July 30, 2001

A number of factors led to the Pirates' 20-year losing streak, but Dave Littlefield's first deal as GM shows that they certainly didn't help themselves on the trade front. Schmidt made three All-Star teams and recorded two top-five Cy Young Award finishes in San Francisco, while Vogelsong almost immediately needed Tommy John surgery and struggled upon his return. Vogelsong figured it out a decade later, after a stint in Japan -- but he, too, did his best work for the Giants.

9. World Series heroes shipped out
Pirates got from Indians: C Gary Alexander, RHP Victor Cruz, RHP Bob Owchinko, RHP Rafael Vasquez
Pirates gave up: RHP Bert Blyleven, C Manny Sanguillen
Date: Dec. 9, 1980
Pirates got from Cubs: INF Sparky Adams, OF Pete Scott
Pirates gave up: OF Kiki Cuyler
Date: Nov. 28, 1927

The Pirates were a little more than a year removed from winning the World Series when they dealt Blyleven, the future Hall of Famer, and the beloved Sanguillen for a return that didn't contribute much. During the 1980 season, Blyleven threatened to retire if he wasn't traded. (It turned out that Sanguillen did, in fact, retire after the '80 season. He never played for Cleveland.) Similarly, the Pirates felt obligated to deal Cuyler two years after his World Series-winning hit in '25 and received little value in return.

10. Called the Doc
Pirates got from Yankees: RHP Doc Medich
Pirates gave up: RHP Dock Ellis, 2B Willie Randolph, LHP Ken Brett
Date: Dec. 11, 1975

Medich, a University of Pittsburgh medical school student at the time of the trade, went 8-11 with a 3.51 ERA in his only season with the Pirates. Ellis' best years were in Pittsburgh, but he was an effective starter for the Yankees in 1976. And Randolph, blocked at second base in Pittsburgh by Rennie Stennett, put together an excellent career as a six-time All-Star and member of the Yankees' back-to-back World Series championship teams in '77-78.