Naturally, the Chicago White Sox shipping Chris Sale to the Boston Red Sox sent shock waves throughout the baseball world. After all, it’s not every day a club sends their ace packing during the offseason.

With the dust now settling, pundits are anointing Boston as the winners of the postseason. They’re also praising Chicago for the haul of prospects they received — infielder Yoan Moncada, outfielder Luis Alexander Basabe, and pitchers Victor Diaz and Michael Kopech. But, are the talking heads right?

Perhaps, Sale will help lead the “Sawx” back to World Series glory. But, that’s not a certainty. At the same time, there are no guarantees that any of the youngsters received by the South Siders will pan out.

Only time will tell.

Since we’ve yet to master time travel at Prospect Insider, we can’t go to the future to see how the Sale deal works out. Instead, I thought it’d be fun to do the next best thing. Look back at previous offseason trades involving aces and reflect about their respective outcomes.

Obviously, reviewing the past won’t help predict the future for Boston and Chicago. But, it could provide perspective, especially after you see the deals I’ve chosen. Some had more layers than others. All were interesting to me.

Johan Santana for Carlos Gomez, Philip HumberKevin Mulvey, Deolis Guerra 
With 17 games remaining, the 2007 New York Mets blew a seven-game division lead and completely missed the postseason. The fallout from this epic collapse included the acquisition of Santana from the Minnesota Twins.

The southpaw certainly didn’t disappoint during his first year with the Mets. Santana was a workhorse leading the National League in starts, innings pitched and earned run average (ERA). Despite his success, his new team — once again — missed the playoffs after being in first place with 17 games remaining.

In fact, the Mets never reached the postseason during Santana’s five seasons in New York. But, he does hold a special distinction — he’s the only Met to throw a no-hitter in the franchise’s 55-season history.

Fans fondly remember the moment, but manager Terry Collins later acknowledged to Phil Taylor of Sports Illustrated that he still harbors regrets for allowing his ace — who missed the previous season due to shoulder surgery — to throw 134 pitches in that game.

Santana was never the same afterwards. He’d make just 10 more starts before being shut down in August. The following Spring Training, he re-injured his shoulder and hasn’t appeared in the majors since.

Gomez never reached his highly touted potential with the Twins and was eventually traded to Milwaukee Brewers for shortstop J.J. Hardy. Minnesota would later flip trade Hardy to the Baltimore Orioles for pitchers Jim Hoey and Brett Jacobson. Neither ever played for the Twins.

The right-handed Humber made just 13 appearances for Minnesota before signing with the Kansas City Royals as a free agent. If Humber’s name sounds familiar to Seattle fans, he threw a perfect game against the Mariners while a member of the 2012 White Sox. Ironically, he played just one more year, ending his career with 97 appearances and a 5.31 ERA.

Mulvey spent little time with Minnesota before dealing him to the Arizona Diamondbacks for pitcher Jon Rauch, who later left via free agency. Guerra never played for the Twins and spent last season with the Los Angeles Angels.

Roy Halladay for Kyle Drabek, Michael Taylor, Travis d’Arnaud
Another team attempting to overcome disappointment were the Philadelphia Phillies, who lost the 2009 World Series and picked up Halladay from the Toronto Blue Jays afterwards.

Halladay immediately impressed by throwing a perfect game during his season in the City of Brotherly. Later that same year, the right-hander pitched a no-hitter during his first career playoff appearance. By doing so, he joined Don Larsen as the only other pitcher to toss a no-hitter in the postseason. Larsen’s effort was a tad better though — a perfect game in the Fall Classic.

Unfortunately, age and injury caught up with Halladay causing him to miss playing time during his last two years in Philadelphia. Ultimately, he’d retire after the 2013 season.

The son of Cy Young Award winner Doug Drabek, Kyle was a first round pick of the Phillies. He never worked out in Toronto and was waived after posting a 5.27 ERA in 30 starts during five big league seasons. Drabek is currently a free agent after spending 2016 in the Diamondbacks organization.

On the same day he was acquired from the Phillies, Taylor was shipped to the Oakland Athletics for prospect Brett Wallace. The following summer, the Jays traded Wallace to the Houston Astros for Anthony Gose. Eventually, the Jays would send the outfielder to the Detroit Tigers for Devon Travis, who’s provided 4.8 wins above replacement in 163 games with Toronto.

I’ll save d’Arnaud for the next segment because he was included in another deal for an ace.

R.A. Dickey, Mike Nickeas, Josh Thole for Noah Syndergaard, Travis d’Arnaud, Wuilmer Becerra, John Buck
This time, the Mets were the ones dealing an ace when they sent Dickey — the reigning 2012 National League Cy Young award winner — to the Blue Jays.

During his stay in Toronto, the knuckleballer was a durable performer, pitching 200-plus innings in three of his four seasons with the club. But, he never repeated the success he enjoyed in the Big Apple. The 42-year-old recently signed with the Atlanta Braves as a free agent.

Thole — Dickey’s long-time personal catcher – is currently looking for a job on the free agent market and Nickeas played in just one game for the Blue Jays before retiring in 2015.

When he burst onto the scene in 2015, Syndergaard lived up to his top prospect billing and helped the Mets reach the World Series during his rookie year. Last season, “Thor” was the club’s ace leading them back to the postseason for a second consecutive year — a feat that’s occurred only once before in franchise history.

Ever since finishing seventh in 2014 Rookie of the Year voting, d’Arnaud has struggled to stay on the field due to injury and inconsistency. To the chagrin of Mets fans, the enigmatic 27-year-old is currently set to be club’s 2017 starting backstop.

Buck played a partial season with New York before the team traded the catcher and Marlon Byrd to the Pittsburgh Pirates for Dilson Herrera and Vic Black. Last summer, the Mets shipped the 22-year-old Herrera a minor leaguer to the Cincinnati Reds for outfielder Jay Bruce.

After pitching for the Mets for two seasons, Black suffered a herniated disk in his neck and spent all of 2015 in the team’s minor league system. He didn’t pitch in professional baseball last season.

The Dickey deal could potentially benefit New York one more time. According to, Becerra ranked seventh in the Mets’ system last season. Only 22-years-old and set to play Class-AAA ball next year, Becerra’s saga has yet to unfold.

Cliff Lee for Phillippe Aumont, J.C. Ramirez, Tyson Gillies
After logging an 85-win season during his first year as Seattle Mariners general manager in 2009, Jack Zduriencik wanted to continue his club’s progress. So, he acquired Lee — a former Cy Young award winner — from Philadelphia.

Unfortunately, the Mariners were hopelessly out of contention by the following July. With Lee set to walk as a free agent, Zduriencik shipped the southpaw and reliever Mark Lowe to the Texas Rangers for prospects Justin Smoak, Blake Beavan, Josh Lueke, and Matt Lawson.

Lee’s stay in the Emerald City may have been brief, but he did perform quite well. In 13 starts, he registered a 2.34 ERA and five complete games.

A former first round pick of the Mariners, Aumont was the highest ranked prospect the club received. He appeared in 46 games over four years with the Phillies before his release during the 2015 season. The right-hander retired this past June.

Gillies spent 2016 playing for two independent league teams and has yet to appear in a major league game, while Ramirez has played for several clubs after leaving Philadelphia in 2013, including the Diamondbacks, Mariners, Reds, and now the Angels. The Halos intend to try the 28-year-old as a starter next season, a role he hasn’t filled since 2011 when he was with Class-AAA Reading.

Although the Phillies didn’t get much in return for Lee, they won 97 games in 2010. Ironically, he returned to Philadelphia as a free agent after that season and finished his career with the club in 2014.

On the surface, the Lee trade was a wash for the Mariners. After all, they acquired him from the Phillies for a group of undistinguished players and received the same from Texas. However, the bigger issue from Seattle’s perspective was Zduriencik missing on a prime opportunity to reinvigorate his organization with quality players.

Zack Greinke, Yuniesky Betancourt for Lorenzo Cain, Alcides Escobar, Jeremy Jeffress, Jake Odorizzi
At the time of this 2010 deal, the Brew Crew were coming off a 77-win season and committed to contending. With that in mind, they shipped a robust package to Kansas City for Greinke and Betancourt.

Just one year removed from winning a Cy Young award, Greinke helped the Brewers reach the 2011 National League Championship Series during his first season with Milwaukee. Yet, the good times didn’t last.

By late July of the following season, Brewers general manager Doug Melvin found his club mired in fourth place with Greinke set to become a free agent. So, he flipped his right-hander to the Los Angeles Angels in a deadline deal for pitchers Johnny Hellweg and Ariel Pena and current Mariner Jean Segura.

Hellweg and Pena had minimal impact on the Brewers, but Segura was an all-star during his first full season. After struggling during the next two years, the shortstop was traded to Arizona in January for Chase Anderson, Aaron Hill and Isan Diaz.

Hill has since moved on. But, Anderson started 30 games for the Brewers last season and Diaz was an top-100 prospect in 2016.

After playing one season in Milwaukee, Betancourt re-signed with the Royals. He’d make two more stops — including one with the Brew Crew — before ending his career in 2015.

The only player who didn’t play a significant role in this deal for Kansas City was Jeffress, who spent part of two seasons with the club before his contract was purchased by Toronto. The remaining players either directly or indirectly contributed to the organization’s greatest success in nearly three decades.

Odorizzi made just two appearances with Kansas City. But, he was part of a trade package that changed the direction of the Royals franchise. The pitcher was sent with Mike Montgomery and Wil Myers to the Tampa Bay Rays for Wade Davis and James Shields.

Known as “Big Game James,” Shields averaged 228 innings pitched during his two-year stay with the Royals and was the club’s ace during their improbable run to the 2014 American League championship.

Davis served as the eighth inning setup man in 2014 and stepped into the closer’s role late in 2015 and was on the mound when Kansas City won their first World Series since 1985. Earlier this week, the Royals sent him to the Chicago Cubs in a swap for outfielder Jorge Soler.

Both Cain and Escobar are still with the Royals. Cain has been one of the top 20 position players during the last three seasons and was the 2014 American League Championship Series Most Valuable Player. The 29-year-old Escobar won the same award the following season and has been the club’s starting shortstop since 2011.

Hopefully, you enjoyed this trip down memory lane. My takeaway from the journey is simple. Previous trades of aces demonstrate why patience should be practiced when crowning winners and losers. That’s a message talking heads should consider before making pronouncements about the Sale deal.


  1. Thanks!

  2. Luke, you bring up trades with lots of talent, much promise and plenty of mixed results for every team. It seems like the KC was the best short-term winners in all the swaps (Greinke to the Brewers for talent that helped the Royals win the WS). The saying that you’ve got to give something to get something is true. I like the way Dipoto has articulated a vision (“CTZ”) and has a clear picture of what he wants. Great examples and takeaway Luke.

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