Trading Star Pitchers

By: David Weiss

The big talk around Metsland is if they should trade Jacob deGrom and/or Noah Syndergaard before the deadline. This is the classic conflict that many teams face. Do you hold onto your ace or do you try to deal them and get as much value as you can in return? There is no easy answer since it can take years until we know if the worked out. Here is a look back at some of the trades for big name starting pitchers since the 1990’s and how they turned out.

Trades that worked out well for the selling team-

1. Mariners trade Randy Johnson to the Astros (1998 trade deadline)

Big Unit
No Mariners fan wanted to see the Big Unit leave. However, the trade was one of the reasons they won 116 games in 2001.

The 1998 Mariners had a disappointing first half. With their enormous lefty ace about to become a free agent, it made sense to trade him. The Astros were willing to part with minor leaguers Freddy Garcia, Carlos Guillen, and John Halama. All three had several really good seasons in Seattle. From 2000-2003 the M’s won 91 or more games each season.

2. Indians trade Bartolo Colon to the Expos (2002 trade deadline)

Big Sexy
A young Bartolo

Prior to being big and sexy, Colon was a very good starter in Cleveland. However, the team was struggling and Montreal thought that if they could stay in the playoff race, it could save their franchise. The Expos gave up minor leaguers Brandon Phillips, Grady Sizemore and Cliff Lee. While the Indians gave up on Phillips too early, Sizemore had four superb seasons for the Tribe. Lee won the 2008 Cy Young award. As a team the Indians nearly made the 2007 World Series.

3. Orioles trade Erik Bedard to the Mariners (Prior to 2008 season)

For a very brief period of time Bedard was a highly regarded pitcher. After an excellent season in 2007, The O’s shipped him to Seattle. In return they got two youngsters named Adam Jones and Chris Tillman. Both were key players in all three playoff seasons that Baltimore had since 2012. Adam Jones in particular has been a five time all-star and a gold glove center fielder.

4. Indians trade CC Sabathia to the Brewers (2008 trade deadline)

While this one wasn’t an overwhelming success, Cleveland got Michael Brantley from Milwaukee. While Brantley has had injuries over the past two years, one thing is abundantly clear. The guy can hit. Since 2012, he has had a batting average over .300 and was just named to his third all star team.

5. Indians trade Cliff Lee to the Phillies (2009 trade deadline)

The Indians love trading aces at the deadline. After Lee took the 2008 Cy Young, Cleveland was having a horrendous 2009 season. As a result, they traded their ace. Philadelphia ended up winning the NL pennant. While most players didn’t pan out, one player they got back in return was Carlos Carrasco. It took him a while to become a good pitcher, but he has been one of the most consistent starters since 2014. This trade is one of the reasons that Cleveland is on pace to win their third division title in a row.

6. Royals trade Zack Greinke to the Brewers (Prior to 2011 season)

By getting Greinke, the Brewers won their division in 2011, but it also helped the KC win it all in 2015.

The Royals were stuck in a dark period that lasted almost three decades. However, in 2009 Zack Greinke won the Cy Young award. He was simply fantastic but the Royals went nowhere. They made one of the least popular trades after the 2010 season when they dealt him to Milwaukee. It took half a decade to realize how great of a trade that was. The Royals got back four young players including Alcides Escobar and Lorenzo Cain. Both were keys to their championship run.

7. Cubs trade Ryan Dempster to the Rangers (2012 trade deadline)

When the Cubs decided to go into tank mode six years ago, they traded Dempster amid his best season. In return they got Kyle Hendricks who has been an excellent pitcher since he was a rookie. Thanks to Hendricks 2016 campaign the Cubs ended the 108 year drought.

8. Mets trade R.A. Dickey to the Blue Jays (Prior to 2013 season)

By sending Dickey to the Jays, the Mets got pieces for their 2015 pennant winning season.

In 2012, Dickey may have been the unlikeliest of Cy Young award winners. After a mediocre career, he joined the Mets in 2010 at age 35 and had a very good season. By 2012 he was untouchable. The Mets traded him and got back Noah Syndergaard and Travis d’Arnaud. Both players were vital to the 2015 World Series. Both have had injuries since. When healthy, Thor is fantastic. Travis d’Arnaud is a good hitter but poor defensive catcher.

9. Cubs trade Jeff Samardzija and Jason Hammel to the A’s (2014 trade deadline)

The 2014 Cubs were well below .500 in July. They had a great pitching but lacked offense. With Hammel on a walk year and Samardzija just a year behind, they traded both for three great prospects. They got back Addison Russell, who was the eleventh overall pick a couple years before. In 2016, he was a key piece to the Cubs championship team. They also got Dan Straily, who was traded shortly thereafter for Dexter Fowler. The third player was Billy McKinney. McKinney was traded to the Yankees for Chapman.

While there is no doubt many trades work our well, there are no shortage of ones that backfire. Here is a list of trades in which the team dealing the ace did not get back the return they hoped for-

1. Blue Jays trade David Cone to the Yankees (1995 trade deadline)

This was bad. Cone was good wherever he went. When Toronto was struggling in the 1995 season, they sent Cone to the Yanks for three prospects. The only one to make the majors was Marty Janzen. He had a terrible rookie season but was ok in his second season out of the bullpen. The Jays let him go to Arizona in the expansion draft but he never returned to the majors. The other two players never made it to the majors. Cone pitched for the Yankees from 1995-2000 and was one of their top pitchers during their championship era.

2. Expos trade Pedro Martinez to the Red Sox (Prior to 1998 season)

Pedro is wearing a ‘B’ on his cap in Cooperstown thanks to a poor trade by the Expos.

The Expos had a tragic history of trading away superstars. None was more glaring then when Pedro was sent to Boston for Carl Pavano and Tony Armas Jr. While in Boston, Pedro had years comparable to Sandy Koufax. Pavano went 24-35 with 4.83 ERA and a WHIP of 1.44 in parts of five seasons. To make matters worse, he improved and went on to win a World Series with the Marlins. Armas put up just slightly better numbers. He went 48-60 with an ERA of 4.45 and a WHIP of 1.415 in eight seasons. To top it all off, Montreal no longer has a baseball team.

3. Yankees trade Jose Contreras to the White Sox (2004 trade deadline)

This is why you don’t give up on a young stud. The Cuban defector pitched well in the Bronx in 2003. However, he struggled in October and the Yankees were not pleased. After a rough start in 2004, Contreras was traded to the White Sox for Esteban Loaiza. In 2005 he settled down and had a great season. He dominated in the postseason and took home a World series ring. Meanwhile, Loaiza pitched in just ten regular season games while putting up an ERA of 8.50, which is why the Yankees let him walk after the season.

4. Twins trade Johan Santana (Prior to 2008 season)

Some trades don’t decimate a team, but they look bad in hindsight. The Twins knew that they couldn’t afford Johan. They traded him to the Mets for four prospects. The big name Minnesota got in return was Carlos Gomez. He was a five-tool player with a lot of hype. He played good defense but was a total offensive bust. Kevin Mulvey and Philip Humber pitched in a combined just 15 with the Twins. Both were gone after 2009. Deolis Guerra never pitched in Minnesota and only got to the majors in 2015. While the Twins did win the division in 2009 and 2010, it was despite these prospects. By 2011, they began a dark age in which the team was unwatchable. Meanwhile, Santana nearly won the 2008 Cy Young award and was a 2009 all-star. He pitched well in 2010 but got injured late in the season. Santana pitched the only no-hitter in Mets history in 2012 but it cost him his career.

5. Phillies trade Curt Schilling to the Diamondbacks (2000 trade deadline)

Curt Schilling winning his first of three rings… after leaving Philly.

In 2000, Philly was stuck. The Braves were winning division titles at an unprecedented rate. The Mets and Marlins were winning wild cards and making the Phillies irrelevant. They thought that if they traded their aging ace, they would be able to get the pieces needed to win. The four players they got back just didn’t achieve that aim. Travis Lee had one decent year in 2001. However, he was a pretty average first baseman. Vicente Padilla had two good seasons in 2002 and 2003, but the other 3.5 seasons in Philly were unremarkable. Omar Daal was a back of the rotation starter and Nelson Figueroa was released after just one season. Schilling went on to win three World Series rings in Arizona and Boston. He also finished second in Cy Young voting three times.

To conclude, there is no straight forward answer. Trading your ace isn’t a guarantee for success. There is only one thing we can be assured of. If we trade deGrom and/or Thor, it will hurt. However, it could turn the franchise around. The Yankee fans were not happy to see Andrew Miller and Aroldis Chapman pitching on opposing teams in the 2016 World Series. However, both trades netted many great prospects which is why the Yankees are one of the best teams in baseball today.

(David Weiss is a lifelong Mets fan. He has lived in Israel since 2008 and runs the Facebook page Jewish Mets Fans.)


  1. I am not a Jewish Met fan. I am a Met’s fan though. I don’t want our best pitcher’s to be traded. I also understand that even though us fan’s enjoy America’s past time, in the long run, just like other businesses the ball players are just employ’s of the team.

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