Five Worst Trades In Oakland Athletics’ History

The Five Worst Trades in Oakland Athletics History

As an Oakland Athletics fan since their arrival in 1968, I have seen some awful trades by the Athletics front office. In choosing the five worst trades, I decided on a few factors.

What would not be included were mid-season trades where a pending superstar in the last year of a contract was dealt away for a future prospect. Thus the 1997 Mark McGwire trade to the Cardinals or the 1993 trade of Rickey Henderson to the Blue Jays (as well as countless others) would not be included, because ownership was basically trying to get something in return for a player who was sure to depart via free agency. Also, because MLB Commissioner Bowie Kuhn negated the trade of Rollie Fingers and Joe Rudi to the Boston Red Sox in 1976 (as well as selling Vida Blue to the New York Yankees), that deal would not be included since it never was official.

Next: The Dynasty Crumbles

Reggie Jackson and Ken Holtzman to the Orioles for Don Baylor – 1976

After three Worlds Championships and five straight AL West crowns, A’s owner Charlie Finley made a surprise move on April 3, right before the start of the 1976 season. He sent superstar Reggie Jackson and 20-game winning pitcher Ken Holtzman to the Orioles in return for outfielder Don Baylor and pitcher Mike Torrez. The move, which took place in 1976, marked the beginning of Finley’s dismantling of the A’s dynasty.

Reggie, the 1973 MVP and only 29 years old at the time of the trade, would go on to be an All-Star eight more times. After being dealt to the Yankees the following season, he continued his stardom in New York, becoming “Mr. October” with the Yankees World Champion teams of 1977 and 1978. He would eventually be elected to the Hall of Fame in 1992.

Baylor played only a single season with the Athletics, where he hit .247 and had 15 home runs.

Next: Bright Lights, Big City for Rickey

Rickey Henderson to the New York Yankees for Stan Javier, Jay Howell, Jose Rijo, Eric Plunk and Tim Birtsas – 1984

After a 77-85 season, the Athletics finished in the middle of the AL West in 1984. That December, the A’s traded Rickey Henderson, who stole over 100 bases in his first five seasons, to the New York Yankees along with Bert Bradley. In return, Oakland received five Yankee players.

Henderson had been an All-Star with the A’s the 1984 season, hitting .293 with 16 home runs and 113 runs scored. For the Yankees in 1985, Rickey finished 3rd in the MVP vote, and led the league in both runs scored (146), and stolen bases (80), and also had 24 home runs, 72 RBIs and a .314 batting average.

Henderson would go on to be an All-Star in all four of his seasons in New York, and would lead the American League in stolen bases in three of those seasons. Fortunately, Henderson, who was elected to the Hall of Fame in 2009, was traded back to Oakland in 1989.

Javier, Howell, Rijo, Plunk and Birtsas never amounted to anything in Oakland Athletics’ lore, although they were involved in some substantial trades that later assisted the A’s in becoming pennant winners. Birtsas was involved in the 1988 trade to the Reds that brought over A’s designated hitter Dave Parker, and Howell was a part of the trade to the Dodgers in 1988 that brought over Bob Welch. Welch became a key part of the A’s starting rotation during their winning championship years of the late 80s and early 90s. Plunk was involved in the deal that brought Henderson back to Oakland in 1989. Javier was traded to the Dodgers in 1990, in a move that brought over second baseman Willie Randolph to fill a void for the 1990 World Series.

Next: Baseball's Best Sent Away

Jose Canseco for Ruben Sierra, Bobby Witt and Jeff Russell – 1992

Athletics fans were stunned on August 31, 1992 when possibly the best player in baseball at the time, Jose Canseco, was pulled from the on-deck circle and it was announced that he had been dealt to the Rangers for Ruben Sierra, reliever Jeff Russell and starting pitcher Bobby Witt. The deal turned out to be a big disappointment, and possibly derailed Canseco from a certain Hall of Fame career.

Canseco, who was also in the news for off-field antics, had been Rookie of the Year in 1986. Just two years later, at age 23, he won the MVP Award after becoming baseball’s first 40-40 man, with 40 home runs and 40 steals. The A’s won the first of three consecutive pennants in 1988, with Canseco as their biggest name. In 1991 he led the AL in homers with 44.

Russell, a closer, wasn’t needed at the time – the A’s had Dennis Eckersley. Witt, who became part of the rotation in 1993 and 1994, went only 22-23 in two seasons with 58 starts. Sierra spent the longest time with the Athletics, lasting until mid-1995, but he turned into a huge disappointment; in 1,560 plate appearances he hit only 60 HRs with a .253 average, and he was a risk in the field with a .963 fielding percentage.

The A’s still made it to the ALCS that year, but were defeated by the Toronto Blue Jays. Had they had Canseco and his abilities, there is no doubt that they would have competed for another World Series title that year.

Canseco has gone on record to state that the move messed with his head and caused him to go into a funk. He hit only .233 with four homers in the last month of 1992 for the Rangers, then bounced around teams. First he played for the Boston Red Sox, then went back to the A’s in 1997 – before stops with the Blue Jays, Rays, Yankees and White Sox until he left baseball in 2001.

Unfortunately, Canseco went from being a superstar with high potential while with Oakland to a what-might-have-been type of player after being dealt.

Next: Trade Messes Team Chemistry

Yoenis Cespedes for Jon Lester – 2014

A trade as stunning as the Canseco deal, 22 years later Billy Beane shocked fans by announcing that outfielder Yoenis Cespedes had been dealt for Jon Lester to boost pitching in the starting rotation.

At the time, the Athletics were the best team in baseball by no small margin. They were 57-33 after 90 games – the best record in baseball by 4.5 games, and rolling. They had already bolstered their pitching staff with a Fourth of July deal from the Cubs obtaining starters Jeff Samardzija and Jason Hammel. The trade also didn’t make financial sense, because Cespedes still had a year on his contract while Lester was to be a free agent at season’s end.

Cespedes was hitting his prime in an All-Star season, with 17 home runs at the time of the trade. In his brief 2.5 seasons with the Athletics, he hit .262 with 66 home runs. He was second in 2012 Rookie of the Year balloting, trailing only the Angels’ Mike Trout.

The deal shook up the Oakland clubhouse and team dynamics. Following the trade, the offensive production plummeted and the A’s went 31-41 the rest of the way, the fourth worst record in the league – including going 15-28 in their last 43 games. The A’s saved themselves from missing the playoffs entirely by making the AL Wildcard Game with an end-of-the-season victory, but they went on to lose to the Royals in the one-game playoff.

It’s hard to judge how Cespedes would have turned out had he stayed with the A’s, but in the last two seasons his BA has hovered at the near .300 mark with an increase in both slugging percentage and OPS.

Next: Say Goodbye to Next Season's MVP?