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The Worst Trades in Pirates History

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Pittsburgh Pirates v Los Angeles Dodgers Photo by Stephen Dunn/Getty Images

As with the previous installment, there’s no science here. This is a subjective list of trades I think were bad. Again, I’m not including trades by the current front office.

Nov. 1928

OF Kiki Cuyler to the Cubs for IF Sparky Adams and OF Pete Scott. This is what happens when you trade a player just to get rid of him. Cuyler was the Pirates’ big star until Paul Waner came along. As the best player on a World Series winner, he’d set the franchise’s single season record for total bases in 1925, a record that still stands. Apparently, though, he couldn’t get along with manager Donie Bush, possibly or possibly not because he didn’t want to bat second. Cuyler went on to the second half of a Hall of Fame career with the Cubs. He batted .360 in 1928 and .355 with 155 runs in 1930 (albeit in extreme high-offense seasons). Adams had two bad years for the Pirates. Scott spent one year with them as a fourth OF and never played in the majors again. To top it off, a few months later, the Pirates sold 21-year-old SS Joe Cronin to a minor league team. Cronin went on to a Hall of Fame career with Washington and Boston.

Sept. 1946

3B Bob Elliott and C Hank Carnelli to the Boston Braves for 2B Billy Herman, RHP Elmer Singleton, OF Stan Wentzel and IF Whitey Wietelmann. I’m not sure why the Pirates traded Elliott, as he was a mainstay in their lineup, putting up an OPS+ of 119 in eight seasons. According to his SABR bio, he just wasn’t as good as they thought he should be. Elliott was a star with the Braves and a big factor in their 1948 pennant. He played five seasons for them and had an OPS+ of 120 or more every year, with an average of 139 and three 100-RBI seasons. Carnelli, Singleton, Wentzel and Wietelmann were nonentities. Herman was a good player nearing the end of a long career that lasted just another 15 games.

Dec. 1947

3B Billy Cox, IF Gene Mauch and RHP Preacher Roe to Brooklyn for RHP Hal Gregg, LHP Vic Lombardi and OF Dixie Walker. Some teams have been better at getting rid of players than the Pirates. Walker was a veteran who was Brooklyn’s most popular player, but he asked to be traded because he didn’t want to be on a team with Jackie Robinson. He had one solid season and one weak season with the Pirates, then retired. Gregg did little with the Pirates. Lombardi had a couple of decent seasons as a swing man. Mauch was a marginal utility player. Cox started at third for all or parts of the next seven seasons for a string of mostly powerful Dodgers teams. He didn’t hit much, but reputedly was very good defensively. Roe spent seven seasons with the Dodgers, posting a remarkable record of 93-37, partly due to a ton of offensive support and partly due to a 124 ERA+. In 1951, he went 22-3.

Oct. 1966

LHP Wilbur Wood to the White Sox for LHP Juan Pizarro. You’d think a team whose long-time relief ace threw a fork ball would have appreciated a knuckleballer. Pizarro had had a string of good seasons as a starter with the White Sox in the early 1960s, but struggled with the Pirates and was sold to Boston in the middle of the next season. He got into parts of six more seasons in the majors but with limited success. Wood had four strong seasons in relief for the White Sox, then moved to the rotation and had four straight 20-win seasons (although he also lost a ton of games). In a five-year stretch, he started 224 games (nearly 45 per year) and completed 99.

Dec. 1967

RHP Harold Clem, LHP Woodie Fryman, LHP Bill Laxton and 3B Don Money to Philadelphia for RHP Jim Bunning. In the mid-1960s, a lot of people thought the Pirates couldn’t get over the top because they lacked an ace pitcher. This was their attempt to get one. Clem never reached the majors and Laxton did nothing of note. Fryman’s career lasted another 15 seasons with a lot of ups and downs. Money had one good and three bad years with the Phillies, but had a long string of above-average seasons as Milwaukee’s starting third baseman. The Hall-of-Famer Bunning went 14-23 with below average ERAs in two seasons with the Pirates, then went on to an often bizarre career as a US Senator.

Dec. 1970

RHP Bruce Dal Canton, C Jerry May and SS Freddie Patek to KC for RHP Bob Johnson, C Jim Campanis and SS Jackie Hernandez. I think a lot of people considered this trade worse than it actually was. Dal Canton’s career lasted another seven years, during which he was a more or less average pitcher both as a starter and reliever. May lasted as a backup catcher for three more years, but his hitting collapsed. Patek was the Royals’ starting SS for nine years, including three playoff seasons. He was a good defensive player and got a lot of media attention due to his very small stature and high SB totals, but he was a bad hitter with a career 79 OPS+. Johnson, the Pirates’ main target, had a couple of solid seasons with them but his career went quickly downhill due to a drinking problem. Campanis played only six more games in the majors. Hernandez alternated at short with Gene Alley for two years and played there every game of the postseason in 1971. He was an atrocious hitter and not great defensively, either.

Dec. 1975

2B Willie Randolph, RHP Dock Ellis and LHP Ken Brett to the Yankees for RHP Doc Medich. A one point, the Pirates had Randolph, Dave Cash and Rennie Stennett all lined up to be Bill Mazerosk’s heir. They traded Cash for Ken Brett and Randolph in this deal, and then Stennett never recovered from a broken leg. After this trade, Brett had a few solid seasons left but nothing great. Ellis went 17-8 the next year, then had one more solid season before his career went downhill. Randolph’s career lasted another 17 years, during which he was a remarkably consistent, slightly above-average hitter, a solid defensive player and a six-time All-Star. The Pirates seemed interested in Medich partly because he had gone to Pitt. He went 8-11, 3.51 for the Pirates and they traded him a year later. His career lasted another six seasons, during which he was a roughly average pitcher.

Prospect Trades

In the space of a few years, the Pirates gave away several pitching prospects, who went on to good careers, for no return.

In July 1977, traded LHP Rick Honeycutt to Seattle for RHP Dave Pagan. Honeycutt went on to a 21-year career. For a decade, he was a usually above-average starter. He then moved to the bullpen and helped Tony LaRussa ruin baseball by becoming the first well known LOOGY. Pagan’s major league career lasted one more game.

In April 1980, traded RHP Larry Andersen to Seattle for RHP Odell Jones. Andersen was old for a prospect at 26. He hadn’t been able to stick in the majors with the Indians and didn’t reach the majors at all in his one year with the Pirates. After the trade, he pitched another 15 years as a reliever, putting up an ERA+ of 121. Jones threw only 54 innings in his second go-round with the Pirates.

In April 1981, traded LHP Dave Dravecky to San Diego for OF Bobby Mitchell. Dravecky had an eight-year career as a starter with a 118 ERA+. His career was cut short by a tumor in his left arm that ultimately required amputation. Mitchell never reached the majors.

Dec. 1980

RHP Bert Blyleven and C Manny Sanguillen to Cleveland for C Gary Alexander, RHP Victor Cruz, RHP Bob Owchinko and RHP Rafael Vasquez. Another example of what happens when you trade a guy just to get rid of him. Blyleven couldn’t get along with Chuck Tanner and supposedly had threatened to retire. Sanguillen did retire after the trade and none of the players the Pirates received did anything at all for them. In fact, the return was rather farcical. Owchinko pitched once for the Pirates and failed to retire a batter, leaving his Pirate ERA at infinity. This was the second time they’d acquired Vasquez and, for the second time, he failed to reach the majors with them. Blyleven won another 131 games in a Hall of Fame career.

Dec. 1984

This wasn’t a very good month for the Pirates. It was especially not a good time to trade for veteran outfielders.

C Brian Harper and LHP John Tudor to St. Louis for 3B Steve Barnard and OF George Hendrick. Harper wasn’t a very good defensive catcher, but eventually put up a 110 OPS+ in six seasons as a starter with Minnesota. Tudor, when healthy, was often spectacular with the Cards. In just under five seasons with them, he went 62-26 with a 146 ERA+. Barnard never reached the majors. Hendrick became a symbol of a very bleak stretch of Pirate baseball, picking up a less-than-flattering nickname.

SS Dale Berra, OF Jay Buhner and LHP Alfonso Pulido to the Yankees for SS Tim Foli and OF Steve Kemp. Berra lasted three more partial, very poor seasons and Pulido did nothing. Buhner went on to hit 310 HRs in a 15-year career. Foli’s return to the Pirates, and the rest of his career, lasted just 19 games. Kemp, a good-to-very-good hitter for eight years, collapsed in his first season with the Pirates and played only another 29 games after that.

Dec. 1998

RHP Jon Lieber to the Cubs for OF Brant Brown. Lieber was a slightly above average, workhorse starter for six years with the Cubs, Yankees and Phillies. Brown was supposed to be the answer in center field for the Pirates, but he fell off a cliff and lasted only two more years.

July 2003

OF Kenny Lofton and 3B Aramis Ramirez to the Cubs for IF Jose Hernandez, IF Bobby Hill and RHP Matt Bruback. This trade was ordered by Kevin McClatchy to rescue the team from his financial mismanagement. The Pirates immediately released Bruback, who never reached the majors. Hernandez was awful the remainder of the year, then returned as Jim Tracy’s pet three years later and was awful again. Hill was a prospect who flopped. Ramirez had a long and very good career, probably in part as a result of getting away from Pittsburgh, where his career had mishandled to a staggering degree. Even if Ramirez hadn’t been included, it still would have been a bad trade, as Lofton was a solid player for another four years. Incredibly, the Pirates threw in money. Even more incredibly, Dave Littlefield insisted publicly that the trade was justified by baseball considerations.