The best trades in Pirates history

I started off trying to figure out the five best and worst trades in the Pirates’ history, but got a little carried away. I didn’t apply any objective standards, but just went with the trades that seemed really good either because of the talent they brought back or the impact on the team’s fortunes. The bad ones come next. I’m not including trades by the current front office.

By far the best trade in the Pirates’ history probably shouldn’t be considered a real trade. Just days before the end of the 19th century, the Louisville Colonels “traded” a huge raft of talent to the Pirates as part of what was essentially a merger. Bud Selig The National League had slated Louisville for contraction and the Colonels’ owner, Barney Dreyfuss, was taking over the Pittsburgh franchise. The Pirates got Honus Wagner, Fred Clarke, Deacon Phillippe, Tommy Leach, Rube Waddell (yes, he pitched for the Pirates for just over a year), Claude Ritchey, Chief Zimmer and five random guys. They gave up Jack Chesbro and three random guys, but Chesbro was “transferred” back to Pittsburgh a few months later. That’s four Hall of Famers in one trade. These players made up most of the team that won the pennant from 1901-03.

As for real trades:

Dec. 1905

3B Dave Brain, OF Del Howard and RHP Vive Lindaman to the NL Boston Beaneaters for RHP Vic Willis. The traded players each had a couple pretty good seasons afterward. Willis won 89 games over the next four years and went 22-11, 2.24 for the 1909 champions. Willis was voted into the Hall of Fame by the Veteran’s Committee.

May 1923

RHP Whitey Glazner, and IF Cotton Tierney to the Phillies for RHP Lee Meadows and IF Johnny Rawlings. Glazner and Tierney did nothing of note and Rawlings was a middling UT player. Meadows won 87 games for the Pirates over the next five seasons, including 19-10 seasons for pennant winners in both 1925 and 1927. Tierney won more lasting fame, though, lending his name to a great website, Cot’s Baseball Contracts.

Jan. 1959

RHP Whammy Douglas, OF Jim Pendleton, OF John Powers and 3B/OF Frank Thomas to Cincinnati for C Smoky Burgess, LHP Harvey Haddix and 3B Don Hoak. This trade played a huge role in the Pirates’ 1960 championship. Douglas never played in the majors again, and Pendleton and Powers did little. Thomas was the Pirates’ big slugger of the post-Kiner era. He struggled for two years after the trade, but later had several pretty good years. Burgess had a 116 OPS+ in six seasons as a catcher with the Pirates. He was also probably better defensively than is sometimes remembered; some fans probably think of the guy who finished his career with four years primarily as a pinch hitter. Haddix went 45-38 in five years with the Bucs and had a famous start against Milwaukee. Hoak had three good seasons with them, putting up 5.4 bWAR, second on the team to Dick Groat, in 1960.

Dec. 1965

LHP Joe Gibbon and UT Ozzie Virgil to San Francisco for OF Matty Alou. Gibbon had several fairly good years in relief for the Giants. Vigil did nothing after the trade. Alou won the batting title in his first year with the Pirates and hit 327 over five seasons with them.

Oct. 1969

OF Frank Vanzin and OF Carl Taylor to St. Louis for RHP Dave Giusti and C Dave Ricketts. This appeared to be a nothingburger trade for a journeyman starting pitcher. Vanzin never reached the majors and Ricketts played just a few major league games afterward. Taylor had a few more seasons as a middling fourth OF. Giusti had been a below-average starter for a number of years, but the Pirates moved him to relief and he was the bullpen ace on a bunch of division champions and one World Series winner. In seven years with the Pirates, he went 47-28, 2.94, with 133 saves, fourth most in team history.

April 1975

RHP Wayne Simpson to the Phillies for OF Bill Robinson. This was an exchange of failed former prospects. Simpson was a talented pitcher who’d struggled with arm problems. He pitched only briefly for the Phillies and had one bad season later for the Angels. Robinson, who’d flopped as a much-touted prospect with the Yankees, resurrected his career starting at age 32 with the Pirates. In eight years with them, he had an OPS+ of 114 and he played a key role on the 1979 champions.

Dec. 1978

RHP Odell Jones, SS Mario Mendoza and RHP Rafael Vasquez to Seattle for RHP Enrique Romo, SS Tom McMillan and RHP Rick Jones. This wasn’t a huge trade in the end, but without it the Pirates’ last World Series win likely wouldn’t have happened. Vasquez, McMillan and Rick Jones never did anything. Odell Jones had some talent, but his career sputtered, I think due to arm problems. Mendoza became famous for . . . well, you know. Romo had two good years for the Pirates before his career went quickly downhill, but the first one was a big one. He pitched in 84 games, going 10-5-5, 2.99. Along with Kent Tekulve and Grant Jackson, Romo formed a bullpen trio that Chuck Tanner worked very heavily in nosing out the Expos for the division title. The following year, in 74 games, Romo went 5-5-11, 3.27. He threw 253 innings in relief in those two seasons.

March 1979

Two random minor leaguers who never reached the majors to Boston for OF Mike Easler. The Hit Man had gotten trapped in the minors for some reason, despite an obviously good bat. He finally got a chance with the Pirates, at first mainly as a pinch hitter in 1979 at age 27. In six years with them, he hit 302/354/474.

July 1986 through Nov. 1988

The Pirates during this stretch made several successful trades that helped build the 1990-92 division winners. It’s a pretty good example of how a team can round itself out with trades without winning the lottery, as the Pirates gave up some value in all of these deals.

RHP Jose DeLeon to the White Sox for 3B Bobby Bonilla. This was a good trade but not lopsided. Despite being the epitome of the hard-luck starter, DeLeon became a very solid rotation fixture for the Cards for four years beginning in 1988, although he had his second 19-loss season in 1990. Bonilla became the Pirates’ cleanup hitter, with three 100-RBI seasons for them, and played a big role on the first two of their three division winners in the early 1990s. He had a long career after Pittsburgh and will be receiving money from the Mets for about as long as there is baseball.

RHP Rick Rhoden, RHP Cecilio Guante and LHP Pat Clements to the Yankees for RHP Doug Drabek, RHP Brian Fisher and RHP Logan Easley. Another trade that was good but not totally lopsided. Drabek became a Cy Young winner and the ace of three division winners. In six years with the Pirates, he went 92-62 with a 118 ERA+. Fisher struggled through two seasons, but never developed. Easley did nothing for the Pirates. Rhoden and Guante each had two good years for the Yankees. Clements eventually had a couple good years as a reliever.

C Tony Pena to St. Louis for RHP Mike Dunne, C Mike LaValliere and OF Andy Van Slyke. Pena played another 11 years and won one more Gold Glove, but his hitting fell off a cliff. Dunne had a big rookie year, going 13-6, but went quickly downhill after that. LaValliere was the Pirates’ primary catcher for six years, much of the time in a very good platoon with Don Slaught. He won a Gold Glove of his own and put up a 102 OPS+. Van Slyke starred for the Pirates for eight years, winning five Gold Gloves and putting up a 124 OPS+.

3B Denny Gonzalez and SS Felix Fermin to Cleveland for SS Jay Bell. This was the most one-sided of these trades. Gonzalez played only a few games afterward. Fermin was the Indians’ SS for five years, but hit very poorly. Bell gave the Pirates an above-average SS for eight years, posting a 102 OPS+ and winning one Gold Glove.

Nov. 1998

LHP Ricardo Rincon to Cleveland for OF Brian Giles. Rincon pitched mostly well as a LOOGY over the next seven years. Giles became one of the best hitters in Pirate history, posting a 1.018 OPS in five years with the team.

Aug. 2003

OF Brian Giles to San Diego for LHP Oliver Perez, OF Jason Bay and LHP Cory Stewart. This trade was forced by Kevin McClatchy’s financial problems. It turned out a lot better than a certain other salary-shedding trade, which I’ll get to in the next installment, because the Pirates didn’t rush into it. This wasn’t a completely lopsided trade, though. Giles had six-plus good seasons with the Padres, just not as good as he’d had with the Pirates as his power dropped off a lot. Bay won the Rookie of the Year award and was the Pirates’ marquee player for six years, posting an OPS+ of 131. Perez had one outstanding year, then was undone by control problems. He later resurrected his career as a reliever. Stewart had arm problems and never reached the majors.