It’s always fun to think about who would do what for other teams. No matter the sport, there are always fans and media who like to predict what a certain player would do if they played their sport in a different uniform. Thanks to trading, we do get to see a lot of scenarios that we as sports fans are very interested in watching play out.
In a lot of cases, things play out quickly and the general public can get a quick feel for which side won the trade. However, in most cases, it takes years to see how things actually play out. In the case of the Milwaukee Brewers trading the Kansas City Royals for Zack Greinke, the team won their division the very next season. It looked like the Brewers won the trade but they traded Greinke the next season and he brought them only that one division title. The Royals, on the other hand, used what they got in that trade to win a World Series a few years later. So while it looked like the Brewers won the deal initially, it was indeed the Royals that got the better end of the stick. It just took a few years longer to see the final outcome of things.
Today we will take a look at several deals made since 2010 that never should have been made. If the Angels knew that Vernon Wells would forget how to hit home runs, do you think they would have traded for him? Do you think that Toronto would still send Noah Syndergaard to the Mets for R.A. Dickey knowing what they do now?
20 Rangers Send Kyle Hendricks To Cubs For Ryan Dempster
As the 2012 trade deadline was approaching, the Chicago Cubs were on their way to another poor season. They were putting 35-year-old Ryan Dempster out for every major league team to have a look at. He was 5-5 on the year at the time and was a solid veteran for a team looking for a fourth or fifth starter.
Chicago had agreed to a deal with Atlanta but Dempster had a no-trade clause and didn’t want to play for the Braves. That’s a good thing for the Cubs as they ended up sending him to the Texas Rangers for Kyle Hendricks, who ended up being a World Series hero in 2016. Dempster was out of the major leagues after the 2013 season.
19 A’s Trade Josh Donaldson To Toronto For Brett Lawrie
In November of 2014, the A’s knew that Josh Donaldson was going to be a free agent and he was going to want a ton of money. Rather than give it to him they shipped him off to Toronto for Brett Lawrie, Sean Nolin, Franklin Barreto, and Kendall Graveman.
The very next year Donaldson won the AL MVP and up until recently, he has been one of the best hitters in the game. Meanwhile in Oakland Graveman turned into a very average starter and Barreto has a bat that could be compared to Bob Eucker’s. Lawrie had one good season before leaving Oakland and Nolin only pitched in six games. Terrible deal by Oakland.
18 Rangers Trade Tanner Roark To The Nationals For Cristian Guzman
When the Texas Rangers were heading to playoffs they wanted a solid veteran bat with some speed to add to their lineup. They brought in Christian Guzman from Washington because he had some speed, a decent glove, and an ok bat. It seemed to be a decent deal at the time for them. However, time has shown that it was far from it.
Texas sent Tanner Roarke to Washington in that deal and he became a stud in their rotation, although he sometimes got lost because of all the great starting pitching they have. Guzman, on the other hand, played only 15 games with the Rangers and hit just .152.
17 Astros Send Michael Bourn To Braves For Four Nobodies
On July 31st, 2011 the Astros were looking to make a change for the future. While they did make a lot of good deals, this one wasn’t one of them. They sent the speedy Michael Bourn to Atlanta for Juan Abreu, Paul Clemens, Brett Oberholtzer, and Jordan Schafer.
Bourn was an All-Star in Atlanta and hit .275 while stealing 64 bases. After the 2012 season, he left and the team got a compensatory first-round draft pick for him.
Abreu pitched six innings in Houston before he moved on to Toronto via waivers. Schafer was low on the depth chart and hardly played before he was also lost on waivers… back to Atlanta. Clemens lasted a bit but has a high ERA and Oberholtzer turned into a third starter at best.
16 Rangers Ship Chris Davis To Baltimore For Koji Uehara
As you can tell, the Texas Rangers have made a host of bad deals. Far too many to mention them all here today. This one in 2011 is just another example of a star player they let go too soon.
When Chris Davis was sent to Baltimore he blossomed into a star and in 2013 he almost won the AL MVP after blasting 53 home runs and driving in 138 runs.
Uehara was average at best in two seasons for the Rangers and only pitched two-plus innings in the playoffs. Those two innings of work saw him give up three homers and five earned runs. Ouch.
15 Phillies Send Hunter Pence to Giants For Joseph, Schierholtz, and Rosin
The Philadelphia Phillies sent Hunter Pence over to the San Francisco Giants in 2012 for Tommy Joseph, Nate Schierholtz, and Seth Rosin. You might ask yourself why this happened and it’s a question that Philadelphia’s front office asks at least once a week. The three players they got amounted to less than nothing and Pence went on to become a star in the Bay area.
Pence has won a pair of World Series championships with the Giants and he is an MVP candidate just about every single season. If the Phillies kept all of the soon to be stars that they have traded away over the years, they would have a dynasty like we’ve never seen.
14 Rangers Send Ian Kinsler To Detroit For Prince Fielder
When this deal was made in 2013 it looked to be a one-sided deal but in favor of the Rangers. They were getting a major power threat in Prince Fielder for Kinsler, who was largely unproven at the time.
Fielder had a decent season in Texas before injuring his neck and retiring. When he walked away from the field the Rangers still owed him more than $100 million.
Kinsler has turned into a very solid second baseman and in recent years his bat has come alive as well. He doesn’t have the kind of power that Fielder once had, but over the course of time, he will hit more home runs after Texas than Fielder did with Texas.
13 Orioles Ship Jake Arrieta To Cubs For Feldman and Clevenger
If a team ever had regrets about a trade gone bad, it would have to be the Orioles for sending Jake Arrieta to the Cubs for basically nothing in 2013.
To that point in his career, Arrieta was simply an average pitcher. Something happened during his plane ride to Chicago though, because he’s thrown multiple no-hitters since and has a Cy Young Award and a World Series ring on his resume.
Scott Feldman was 5-6 with the Orioles before bolting via free agency and Steve Clevenger played three years there but only got into 69 total games, hitting a measly .259.
12 Rockies Send Jeremy Guthrie To Royals For Jonathan Sanchez
In 2012, Kansas City shipped Jonathan Sanchez to Colorado for Jeremy Guthrie. The trade didn’t make a mark on the best or worst of the year because both pitchers were struggling.
Jonathan Sanchez had been doing horribly for the Royals and the Rockies thought a change of scenery would be good for him. It didn’t really work out that way as he actually got worse. After the trade, he played for Colorado and Pittsburgh and totaled only eight appearances over the rest of his career. During those, he had an ERA of over ten.
Jeremy Guthrie didn’t set the world on fire in Kansas City but he at least played well enough to get a new contract. The Rockies should have kept him.
11 Cleveland Gets Corey Kluber For Jake Westbrook
At the trade deadline in 2012, the Indians got Corey Kluber from the Padres in a three-team deal. Jake Westbrook left Cleveland for St. Louis in the trade.
Westbrook had been an average third starter for the Indians and he performed exactly the same for the Cardinals. On the other hand, Kluber turned into a star the next season when he became part of the Indians starting rotation. The season after that he put together an 18-9 season and won the AL Cy Young Award.
San Diego is another team that has made its fair share of terrible deals and this one is in their top five all-time worst. They got Ryan Ludwick in the deal and his performance in two seasons there was forgettable.
10 Arizona Ships Adam Eaton Away For Mark Trumbo
Back in 2013, the Diamondbacks were part of the three-team trade with the Angels and White Sox. In the deal, they sent Adam Eaton to Chicago. The previous year Eaton had hit .381 in AAA and was considered a top prospect.
The Diamondbacks got Mark Trumbo from the Angels in the deal and during his season and a half there he put up the worst numbers of his career. He was traded to Seattle and then moved on to Baltimore where he once again started hitting home runs.
In Chicago, Eaton turned into a solid star and even added some pop to his stats, which he hadn’t shown before the trade. Arizona would have been far better off if they had kept Eaton. Why would you trade a guy who just hit .381 anyway?
9 Arizona Sends Ian Kennedy to Padres For Practically Nothing
On July 31, 2013, the Arizona Diamondbacks sent Ian Kennedy to the San Diego Padres in a trade that made absolutely no sense at all. They got Matt Stites and Joe Thatcher in return and neither did a thing in the desert at all. Thatcher was dealt to the Angels less than a year later and Stites pitched forty-one terrible innings with Arizona.
Kennedy had pitched very well in Arizona, although he had struggled some that season at the time of the deal. He played decently for the Padres going 26-30 before moving to Kansas City. While 26-30 isn’t all that spectacular, it’s much better than what Arizona got in return for him.
8 Blue Jays Trade Noah Syndergaard and Travis D’Arnaud For R.A. Dickey And Josh Thole
Why would you trade a Cy Young Award winner away shortly after he received his award? It’s hard to give a good answer to that question but obviously, the Mets knew that R.A. Dickey’s award-winning performance was going to be his last. After he took home the Cy Young in 2012 he was sent with Josh Thole to Toronto for Syndergaard and D’Arnaud.
As the Mets expected, Dickey went into the toilet while in Toronto while Syndergaard became a star in New York. The Mets have him locked up until at least 2022. Dickey’s now 44 years old and his career is over. The Blue Jays really screwed that one up.
7 Giants Trade Zack Wheeler to Mets for Carlos Beltran
When the San Francisco Giants sent Zack Wheeler to the Mets for Carlos Beltran, they had three things in mind. They were hoping for a solid performance and a deep playoff run, and they were hoping he would sign a contract extension to stay with the team. Well, they got one of the three.
Beltran played well in his 44 games that year, blasting 7 home runs and driving in 18 runs while hitting well over .300. However, the team didn’t make the playoffs and Beltran bolted for St. Louis via free agency after the season.
Wheeler hasn’t been a Hall-of-Fame candidate for the Mets but he has posted a record of 33-30 and his 95 games for New York far outweighs what Beltran did in San Fran.
6 Cubs Get Anthony Rizzo and Zach Cates From Padres For Cashner and Kyung-Min Na
For some reason in 2012, the Padres shipped Anthony Rizzo and Zach Cates to the Cubs for Andrew Cashner and Kyung-Min Na.
Cashner pitched in 130 games for the Padres and put together a record of 28-43. During his stay in southern California, he was flat out terrible. Things haven’t gotten any better for him as he just wrapped up a 4-15 season in Baltimore. How he keeps getting spots on major league rosters is mind-boggling.
Rizzo, on the other hand, has blossomed into a superstar. He plays first base every day for the Cubbies and he just finished this season with 24 homers and 100 RBI’s. The home run total is lower than his previous several seasons but his average was up and he still knocked in a hundred.
5 Phillies Trade Jonathan Papelbon to Nationals
When the Phillies were trying to get rid of Jonathan Papelbon they didn’t find a lot of interest. Once one of the top closers in the game, he was now largely ineffective and had major attitude problems. Philadelphia pretty much gave him to Washington for nothing and the Nationals watched their once-promising season go right down the toilet when the trade was completed.
Papelbon blew save after save with the Nationals but made everything worthwhile when he tried to choke out Bryce Harper in the dugout on national television. Sometimes no move is better than any move and Washington found this out big time when they brought in Papelbon.
4 Cubs Send Jeff Samardzija to Oakland For Addison Russell
Shortstop Addison Russell is facing severe punishments from major league baseball right now for his part in a domestic abuse situation. While all of the details still have not come out, he was placed on suspension with pay by MLB for the rest of the regular season.
Before all of this became public he was part of a lopsided trade when the Cubs sent Jeff Samardzija to Oakland for the shortstop. Jeff played in only 16 games for Oakland, putting together a very unimpressive record of 5-6 during his only season there. Russell has become a superstar in Chicago and if he is ever allowed to play again, that should continue.
3 Angels Get Vernon Wells From Toronto For Mike Napoli
In 2012 ,Vernon Wells had a great season with the Blue Jays. He pounded 31 round trippers and it looked like he had at least four to five good years left in him because he was 32 years old.
Toronto thought otherwise and dealt him to the Angels for Mike Napoli. They were right as Wells immediately forgot what a home run was and his two seasons with the Angels were far short of heavenly.
Toronto used Napoli as trade bait a couple of days later and they brought in Frank Francisco. Frank saved 17 games in his only season north of the border and it seems like a fair deal for a team that knew Wells was finished. It’s too bad the Angels didn’t know it.
2 Brewers Get Zack Greinke and Betancourt For Cain, Escobar, and Odorizzi
After the 2010 season, the Brewers thought they were getting a steal when they brought in Zack Greinke and Yuniesky Betancourt from the Royals in exchange for Lorenzo Cain, Alcides Escobar and Jake Odorizzi. At first, it looked good as the Brewers won the division title behind their star pitcher.
However, the next season Greinke was in the final year of his contract so they dealt him to the Angels. He was 25-9 in just a season and a half with the Brew Crew, while what the Royals got back led them to a World Series Championship in 2015.
Milwaukee mortgaged their future for winning now and it didn’t work out. It worked out just fine for the Royals though.
1 Miami Marlins Send Giancarlo Stanton To The New York Yankees
This trade is only one season old and still needs ample time to evaluate. But let’s face it, Giancarlo Stanton is one of the most prolific power hitters in the game today and his trade from the Marlins to the Yankees should never have been allowed by MLB.
Miami got back Starlin Castro, Jose Devers, and Jorge Guzman. Sure, Castro has been an All-Star four times but he isn’t anywhere close to the caliber of player that Stanton is.
Stanton just finished his first year in New York with 38 homers and 100 RBI’s. Those numbers are down a bit from what he normally does but give it time. Once he is used to playing in Yankee Stadium (next season) he should be back to fifty homers and 120 or more RBIs. On the other hand, the Marlins have no future at all anymore.