Jun 6, 2020 9 min read

With word that pitcher Chris Archer will miss the 2020 season – if there is one – after undergoing surgery to relieve symptoms of thoracic outlet syndrome, an already bad trade in Pittsburgh Pirates history became even worse.

Archer, who was acquired at the trade deadline in 2018 from Tampa Bay, has an $11 million club option for 2021, with a $250,000 buyout. The Pirates aren’t expected to pick up the option.

So Archer’s time with Pittsburgh appears over and his name will go down in what is surely one of the franchise’s biggest blunders.

Here is one reporter’s list of the Pirates’ best trades and their worst:

10 best trades

Dec. 8, 1899

• The Pirates acquire shortstop Honus Wagner, Fred Clarke, Deacon Phillippe, Rube Waddell and eight other players from the Louisville Colonels for Jack Chesbro, George Fox, Art Madison, John O’Brien and $25,000. Wagner became one of the all-time greats and had more than 3,400 hits. Clarke was elected to the Hall of Fame after a long career as a player and manager, Phillippe won three games in the first World Series and Waddell also was elected to the Hall of Fame. Pittsburgh did give up Chesbro, a Hall of Fame pitcher who would set the single-season wins record when he went 41-12 for the New York Yankees in 1904.

Jan. 30, 1959

• The Pirates sent Frank Thomas Whammy Douglas, Jim Pendelton and Johnny Powers to the Cincinnati Reds in exchange for Smoky Burgess, Don Hoak and Harvey Haddix. The trade solidified the Pirates 1960 World Series team. Haddix, who would pitch baseball’s greatest game in 1959 and was the winning pitcher in game 7 of the 1960 World Series. Hoak finished second in the MVP voting in 1960.

April 1, 1987

• On a day when an ice storm shuts down much of Western Pennsylvania, the Pirates trade their most popular player, catcher Tony Pena, to the St. Louis Cardinals for outfielder Andy Van Slyke, catcher Mile LaValliere and pitcher Mike Dunne. It was one of several trades that brought in the cornerstones of three division championship teams.

March 25, 1989

• Pittsburgh deals shortstop Felix Fermin and Denny Gonzalez to Cleveland and obtain shortstop Jay Bell from the Indians. Bell solved Pittsburgh’s nagging shortstop problem and was a two-time all-star.

July 23, 1986

• Pittsburgh trades pitcher Joe DeLeon, who had gone 3-22 in his last 25 decisions with the Pirates, to the Chicago White Sox for outfielder Bobby Bonilla. The Pirates corrected the mistake of leaving Bonilla unprotected in the Rule 5 draft and reacquired him. He became a four-time all-star with Pittsburgh.

Nov. 26, 1986

The Pirates sent pitchers Rick Rhoden, Cecilio Guante and Pat Cle

• ments to the New York Yankees for pitchers Doug Drabek, Logan Easley and Brian Fisher. Rhoden won 28 games in two seasons in New York, but Drabek won the 1990 NL Cy Young and two postseason games. Fisher was promising until injuring his arm.

June 28, 1979

• Pittsburgh acquires third baseman Bill Madlock, infielder Lenny Randle and pitcher Dave Roberts from San Francisco for pitchers Ed Whitson, Fred Breining and Al Holland. Madlock is the final piece to the Pirates’ 1979 world championship team. Randle never played for the Pirates and ended up as a coach for the Washington Wild Things in 2013. Whitson, Breining and Holland each had good years for the Giants.

Nov. 18, 1998

• Pittsburgh obtains outfielder Brian Giles for relief pitcher Ricardo Rincon. Giles spent five years on some bad Pirates teams but he was a two-time all-star and hit at least 35 home runs four times for Pittsburgh. Rincon was the definition of a lefthanded relief specialist.

Feb. 19, 2012

• Prior to spring training, the Pirates acquire pitcher A.J. Burnett and cash from the New York Yankees in exchange for pitcher Diego Moreno and outfielder Exicardo Cayones. The Yankees, wanting to rid themselves of Burnett, agree to pay $20 million of the $33 million remaining on his contract. With Pittsburgh, he wins 43 games in four years and helps the Pirates end their long streak of seasons without a postseason appearance. Moreno and Cayones play a combined nine games in the majors.

Nov. 5, 1976

• The Pirates give catcher Manny Sanguillen and $100,000 to Oakland for manager Chuck Tanner, who would guide Pittsburgh to the world championship in 1979.

10 worst trades

Dec. 12, 1984

• Pitcher John Tudor and utilityman Brian Harper are sent to St. Louis in exchange for outfielder George Hendrick and corner infielder Steve Barnard. Tudor won 21 games and led the league with 10 shutouts in 1985 as the Cardinals won the NL pennant. Harper played 16 years in the majors and had a .295 career batting average. Though he was a four-time all-star with St. Louis, Hendrick was one of the most unpopular Pirates players ever and lasted only 69 games with the Bucs before being traded.

July 31, 2018

• At the trade deadline, Pittsburgh acquires pitcher Chris Archer for outfielder Austin Meadows and pitchers Tyler Glasnow and Shane Baz. When the trade was made, it was considered a bold but good move by then-Pirates GM Neal Huntington. That evaluation changed rapidly. Glasnow is only 7-6 with Tampa Bay and spent much of last season on the injured list, but Meadows hit 33 home runs a year ago, his first full season in the majors. Archer, meanwhile, has been a bust, producing a 6-12 record. His ERA last year was a career-worst 5.19. With time, this could easily move to the top of the worst trades list.

Dec. 9, 1957

• Pittsburgh native Bob Purkey is traded by the Pirates to Cincinnati for pitcher Don Gross. Purkey develops into a five-time all-star pitcher and went 23-5 in 1962. Gross won six games over three seasons as a relief pitcher for the Pirates.

Dec. 8, 1947

• The Pirates traded pitcher Preacher Roe and infielders Billy Cox and Gene Mauch to the Brooklyn Dodgers in a deal for Dixie Walker, Hal Gregg and Vic Lombardi. Roe and Cox became key members of the Dodgers’ “Boys of Summer” team. Lombardi, a pitcher, was the best of the Pirates’ haul, going 15-19 over three years.

Nov. 19, 1962

The Pirates trade short

• stop Dick Groat, the 1960 NL Most Valuable Player, and Diomedes Olivo to St. Louis in return for shortstop Julio Gotay and pitcher Don Cardwell. The Cardinals went to the World Series with Groat in 1964. Cardwell had a pair of 13-win seasons with Pittsburgh but Gotay played in only seven games over two seasons.

Oct. 12, 1966

• Pitcher Wilbur Wood is traded to the White Sox for Juan Pizzaro. Wood, a knuckleballer, becomes a four-time 20-game winner. Pizzaro won nine games over two seasons in Pittsburgh.

July 30, 2001

• In another trade deadline deal, Pittsburgh sent pitcher Jason Schmidt and outfielder John Vander Wal to San Francisco in exchange for outfielder Armando Rios and pitcher Ryan Vogelsong. Schmidt underachieved in Pittsburgh but was a three-time all-star in San Francisco, went 48-20 in his first three years with the Giants and was the runner-up for the Cy Young in 2003. Vogelsong won 10 games over four years with Pittsburgh before being injured. Rios played only 78 games in a Pirates uniform.

June 4, 1953

• Pittsburgh sent Ralph Kiner, Joe Garagiola, Howie Pollet and Catfish Metkovich to the Chicago Cubs for Roby Atwell, Bob Schultz, Preston Ward, Gene Freese, Bobby Addis, Gene Hermanski and $150,000. Kiner led the National League in home runs seven years (and walks three times) in a row with Pittsburgh.

Oct. 24, 1984

• The Pirates send shortstop Dale Berra and minor-league outfielder Jay Buhner to the New York Yankees for shortstop Tim Foli and outfielder Steve Kemp. Foli and Kemp each were washed up and Buhner would hit 310 career home runs.

Dec. 16, 2004

Pittsburgh acquired Benito Santiago from Kansas City for pitcher Leo Nunez. Santiago was a broken down catcher by the time the Pirates acquired him. He played only six games with Pittsburgh before being released. Nunez, whose real name was revealed to be Jose Carlos Oviedo, was a relief pitcher who had 92 saves from 2009 to 2011 for the Marlins.