Power Ranking The Most Important MLB Trades Of The 1990's

The 1990's were a pretty amazing time to be a baseball general manager. You had some of biggest free agent signings ever from Greg Maddux to the Braves and Barry Bonds to the Giants…in the same off-season. There were also four brand new expansion teams that decade. Finally, the trades had massive impact. Here are what I consider the most important MLB trades of the 1990's:

10. The Toronto Blue Jays trade David Cone to the New York Yankees for Marty Janzen and two minor leaguers (7/28/1995)

This list was harder to put together than I thought it would be. I left off some big trades: Jeff Kent to the Giants and Roger Clemens to the Yankees. Those are two guys that have Hall of Fame resumes. I am sure many reading this might disagree but I see the Cone deal as more important. 

Cone was a Yankee during the entire four title run. I think that really matters. David Wells also had to be traded to get Roger Clemens and those Yankee teams were so good, I think they would have won with Wells or Clemens. That trade didn't have the same impact. Cone's story was so amazing coming back from an aneurysm in his arm and throwing a perfect game. Not only that but this list has a lot of lopsided trades in it but this is right up there with the worst of them. This was the trade that put the Yankees over the top.

Jeff Carlick. Getty Images.

9. The Los Angeles Dodgers trade Pedro Martinez to the Montreal Expos for Delino DeShields (11/19/1993)

This isn't a trade about what the Expos gained as much as what the Dodgers lost. The Expos were never going to be able to afford Pedro but we'll talk about that trade later. Imagine if the Dodgers had just kept Pedro? It almost happened too. Jody Reed was the Dodgers second basemen and was a free agent heading into that off-season. Reed had an insane contract request asking for a three year deal at big money for the time. The Dodgers were so furious, they traded for DeShields.

Let's say Reed isn't greedy and the Dodgers keep Pedro. Imagine him heading up that strong rotation into the 1990's with Mike Piazza, Raul Mondesi and Eric Karros in the lineup? Even without Pedro, they still went to the playoffs in 1995 and 1996. Maybe the Dodgers never trade Mike Piazza? The Dodgers history was forever altered because Jody Reed wanted too much money.

Ezra Shaw. Getty Images.

8. The Florida Marlins trade Mike Piazza to the New York Mets for Preston Wilson, Ed Yarnall and a minor leaguer (5/22/1998)

I can't believe the Piazza deal is only eighth on this list. I don't even have the deal that preceded it a week earlier (Piazza and Todd Zeile to the Marlins for Bobby Bonilla, Charles Johnson and Gary Sheffield). That deal had the bigger names but the impact was pretty limited. 

I'd have Piazza higher if the Mets had won a World Series while he was in Queens. He did get the Mets to the 2000 World Series and the home run in the game back from 9/11 is one of the biggest moments in New York City sports history. This is just a really stacked group.

7. The Cincinnati Reds trade Paul O'Neill to the New York Yankees for Roberto Kelly and a minor leaguer (11/3/1992)

This isn't a list of best players of the 1990's. It's the most important trades. Paul O'Neill was the heart of the best of the best team of the decade. He was also really fucking good. He won a batting title and went to four All-Star Games with the Yankees. You can make a really good case that the Yankees dynasty ended when he retired.

It's hard to believe but Yankee fans were pissed when this deal was made. Roberto Kelly was considered to be the next great Yankee. He was only 27 years old and made his first All-Star game the season before he was dealt. Kelly wound up having a decent 14 year career but his power never really developed and his great speed vanished after leaving the Bronx. 

Jed Jacobsohn. Getty Images.

6. The Oakland A's trade Mark McGwire to the St. Louis Cardinals for T.J. Mathews, Eric Ludwick and Blake Stein (7/31/1997)

I have a really hard time ranking this trade on the list. I don't have the Sammy Sosa trade to the Cubs on here at all. Maybe I should have both ranked higher? Maybe I shouldn't even have either on the list? Neither even went to a World Series with the clubs they were traded too. I just can't completely ignore the home run chase of 1998.

It's not the just the fact these guys cheated but the direct result of the steroids here. Sammy Sosa was a decent but not great player before steroids. McGwire was an aging power hitter who couldn't hit for contact and whose body was falling apart. I don't think there is a right answer here but I am confident that neither of those trades should be in the top five.

Focus On Sport. Getty Images.

5. The San Diego Padres trade Fred McGriff to the Atlanta Braves for Melvin Nieves, Donnie Elliott and a minor leaguer (7/18/1993)

Believe it or not, the Braves in the first half of 1993 were kind of a mess. They had just signed Greg Maddux but hadn't been the dominant team everyone expected. At the time of the McGriff deal, they were 52-40 and 9 games back of the Giants (who just signed Barry Bonds). Once they got McGriff, they became red hot and caught the Giants on the last day of the season to win the NL West. In 1995, he helped the Braves win the World Series.

This is one of the most instantly successful mid-season trades in baseball history. I know McGriff chose to have no team on his Hall of Fame plaque cap but he really should've picked the Atlanta Braves for a logo.

Donald Miralle. Getty Images.

George Gojkovich. Getty Images.

4. The San Diego Padres trade Gary Sheffield and Rich Rodriguez to the Florida Marlins for Trevor Hoffman, Jose Martinez and Andres Berumen (6/24/1993)

This trade was so monumental, it gets two pictures. The Marlins made the move to get Sheffield in their first year of existence to try to give new Miami fans something to get excited about. The Padres were in the middle of a massive fire sale and dealing everyone with any value away (see the McGriff deal above). 

Sheffield wound up helping the Marlins win the 1997 World Series. He was there for the entire journey from expansion team to World Champions to them dealing him off in their own fire sale in 1998. The Padres wound up with the second greatest player in franchise history. Looking back, I'm not sure which team "won" this trade. I lean towards the Marlins because they won but who would be the living face of the Padres if they didn't get Hoffman?

Ron Vesely. Getty Images.

3. The Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Andersen (8/30/1990)

The 1990 Red Sox were in a tight division race with the Blue Jays and thought they were all set at first base with Mo Vaughn already in the system. In hindsight, it's absolute madness to trade a future Hall of Famer for a middle reliever who is 37 years old. To make it even worse, the Red Sox already had traded away a great relief pitcher in Lee Smith back in May of that year.

You could make a case that this should be number one on this list. Bagwell and Craig Biggio are the people you think of first when you think of the Astros. The only reason I don't have this higher is because the Astros could never win a title while he was there. The one pennant they did win while he was there, Bagwell was already past his prime.

STAN HONDA. Getty Images.

2. The Montreal Expos trade Pedro Martinez to the Boston Red Sox for Tony Armas and Carl Pavano (11/18/1997)

This was the moment when things really started to change for the Red Sox. This was before Manny Ramirez signed with Boston. It was before Jason Varitek, Trot Nixon and Derek Lowe became really good. The 1997 Red Sox had a losing record and trading for Pedro changed…everything.

The Red Sox did only win one World Series with Pedro but his impact is even felt today. Before Pedro, the Red Sox were known as losers. Teams that could always get close but always fail in the end. With Pedro, he felt like the embodiment of hope. He was better than great in 1999 and 2000. It was the baseball equivalent of man walking on the moon. People could explain all day what you were watching but it was still hard to believe. He was that good.

CHRIS WILKINS. Getty Images.

1. The San Diego Padres trade Joe Carter and Roberto Alomar to the Toronto Blue Jays for Fred McGriff and Tony Fernandez (12/5/1990)

The Blue Jays traded away a 26 year old future Hall of Famer and still won the trade. For the decade before this, Toronto was a very good team that could never get over the hump. They had to make a major move. Blue Jays GM Pat Gillick had that much confidence  in Alomar's potential to pull the trigger on this deal. It's pretty ballsy. McGriff had led the league in home runs already. Fernandez was a four time Gold Glover.

Gillick's confidence was rewarded. Alomar became the key figure on a Blue Jays team that won the World Series in 1992 and 1993. Alomar is the only player in Cooperstown with a Blue Jays logo on his cap. He was only there five seasons but was the best player on a repeat World Champion.

As for Joe Carter?