Well, here we are.  It’s time to unveil the last spot on my countdown of the five worst trades in baseball history.

For No. 1, I’ve chosen a trade that seemed beneficial to both teams at first, but didn’t have a big payoff on either end.  One team won the World Series the year of the trade, and the other team was mostly mediocre over the next five years or so. 

This is the story of that trade, when one legendary team received an injury prone All-Star, and another received a pitcher who wasn’t bad by any means, but still totally glorified.  I’ve set the stage for you all, now let’s get to the story!

In the 1980s, two teams that consistently made the playoffs in the National League were the Los Angeles Dodgers and the St. Louis Cardinals.  Honestly, what can I say about these two teams that hasn’t already been said.  Two legendary franchises with so much history surrounding them, many World Series titles between the two, and so many Hall-of-Fame players coming out of both systems.

In 1988, the Cardinals certainly had the upper hand regarding overall success.  They had won the World Series in 1982 and had returned again in 1985 and 1987, when they lost to the Kansas City Royals and the Minnesota Twins.  The reason behind their success was the perfect balance of role players, from the power-hitting Jack Clark to future Hall-of-Fame shortstop Ozzie Smith.

Their pitching, despite not having many big name players, was remarkably consistent.  Young closer Todd Worrell provided an iron-willed stopper out of the bullpen, and the starting rotation featured a man who despite not having overwhelming “stuff,” went out on the mound and did his job whenever he got the call.  His name was John Tudor.

Before coming to St. Louis via a trade in 1985, John Tudor had established himself as an above average, yet reliable starting pitcher for the Boston Red Sox and Pittsburgh Pirates.  At best, he was a very Andy Pettitte-like pitcher in the fact that his pitches weren’t overwhelming, yet still got hitters out, and he averaged around 13 wins a season with an ERA mid to high three range.

In 1985, however, he had a breakout season in his first season with the Cardinals.  He finished the season with a record of 21 wins and eight losses (after starting the season 1-7!!), and his ERA was a stellar 1.93.  Had it not been for Doc Gooden’s career year (24 wins, four losses, 1.54 ERA), Tudor would have easily won the NL Cy Young Award.

Tudor did well the following seasons, but was nowhere near as dominant as he was in 1985.  He missed most of the 1987 season with an injury and in 1988, team management chose to trade him to the Los Angeles Dodgers.  On one end, it could have been considered a helpful trade, but there was ultimately no payoff for either team.

The 1988 season was a great one for the Los Angeles Dodgers.  The team was blessed with a great pitching staff led by young aces Orel Hershiser and Tim Leary, and a tough bullpen featuring a bevy of young arms (Alejandro Pena, Jay Howell and the late Tim Crews, just to name a few).  Their starting lineup, while not overwhelming, was led by veteran outfielder Kirk Gibson and speedy infielder Steve Sax. 

While the team was doing very well and expected to make the playoffs, there was no doubt that they would have to face a powerful New York Mets team that was just two seasons removed from winning the 1986 World Series. So while the Dodgers’ pitching was good, another arm was needed.

In the Dodgers’ trade discussions with other teams, one name that constantly came up was that of outfielder Pedro Guerrero.  Now, regarding stats, Pedro Guerrero was not by any means a bad player.  He consistently hit well for average, had a good power bat and was instrumental in helping the team win the 1981 World Series over the heavily favored New York Yankees. 

However, in the years preceding 1988, team management had grown tired of Guerrero.  He had missed time with injuries and unfortunately had developed a lackadaisical attitude.  With all three outfield positions occupied by Gibson and young stalwarts Mike Marshall and John Shelby, there was simply no room for Guerrero.  Thus, in negotiations with the Cardinals, the Dodgers sent over Guerrero in return for John Tudor.

Now at first glance, this trade appears to have served the Dodgers well.  In nine regular starts with the Dodgers in 1988, Tudor posted a 4-3 record with a 2.41 ERA as the team clinched the NL Western Division. He upset the heavily favored Mets in the playoffs, and beat the Oakland Athletics in the World Series, four games to one.

However, as much as I hate to say it, John Tudor cannot receive any credit for the team’s postseason success.  He was underwhelming in the two starts he made, and didn’t receive a decision in either.  In 1989, he only appeared in six games (three starts) due to a serious elbow injury. 

After that season was over, he was granted free agency and returned to the Cardinals on a one-year contract.  He finished the season with a 12-4 record and a 2.40 ERA, but was forced to retire because of arm problems.  While trading for him might have been a good idea at the time, I ask that you consider this.  The Los Angeles Dodgers haven’t been to the World Series since 1988 and after winning then, didn’t win another postseason game until 2004.

On the other end of the trade, history didn’t treat the Cardinals much better.  Although in 1989 (his first full season with the team), Pedro Guerrero played in all 162 games and had an MVP-caliber season in which he batted .311 with 17 home runs and 117 RBI, age caught up with him the remaining seasons and he was never the same player. Subsequently, the Cardinals failed to make the playoffs for all of the seasons Guerrero was part of the team.

Now let’s go back to the Dodgers’ end again.  I’m going to be honest.  As well as John Tudor did for them in the regular season, I still think they would have won the World Series without making the trade.  Their pitching rotation was unbelievable with Hershiser, Leary, and let’s not forget about Fernando Valenzuela! 

Plus, even though Guerrero appeared to have worn out his welcome, that doesn’t take away from the fact that in years past, he was a valuable bat for the Dodgers.  With the DH rule in effect in certain games of the World Series, who is to say that he wouldn’t have been able to help the team as a handy power bat coming off the bench?

The backlash from the trade didn’t hurt the Cardinals as badly.  They regained their stride in the mid-90s and consistently made the playoffs, winning the World Series again in 2006.  Would hanging onto John Tudor have kept them as contenders in the National League throughout the 80s without a slump period?  I’m really not sure. 

Regardless, this trade was a textbook case of teams getting used to one type of performance from the players involved and growing tired of them once they started slowing down.  Looking at it from the players’ perspectives, it’s sad that even in baseball today, many owners and management teams still don’t realize that patience is a virtue.

That’s my countdown of the five worst trades in MLB history.  Hope you enjoyed it and stay tuned for more articles coming each day!

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