MLB Trade Deadline: 20 wackiest trade stories in league history

MLB History (Photo by Mitchell Leff/Getty Images)
MLB History (Photo by Mitchell Leff/Getty Images)
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MLB trades always bring a level of excitement to a fanbase. Whether your squad is the favorite to win the pennant or at the bottom of the food chain, a trade can change it all. A new player, releasing old veterans, acquiring cap space, or getting your hands on a highly touted prospect, trades come in all shapes and sizes.

With that said, we’re positive you’ve never seen trades quite like the ones we’re about to break down.

While most transactions make sense, there are plenty of instances where fans had to take a double look. MLB history is littered with some of the most awkward and ridiculous trades imaginable. They didn’t happen often, but when they did, they were head-scratchers.

With so many out of this world trade scenarios, we’ve decided to take a look at which we’re the most outlandish and craziest in MLB history. We can assure you that we didn’t make any of this up. And truth be told, the likelihood of these trades taking place in today’s day and age is slim to none.

Prepare to take a look at the wackiest trades in MLB history.

Los Angeles Angels logo (Photo by Jayne Kamin-Oncea/Getty Images)
Los Angeles Angels logo (Photo by Jayne Kamin-Oncea/Getty Images) /

Wackiest MLB trade stories in league history: 20. The Los Angeles Angels get Mike Cisco for free

It’s all about being fair when it comes to trades. Sometimes on the surface, things can appear to be a bit one-sided. Especially when in MLB transactions.

When it comes to other sports leagues such as the NBA and the NFL, active players that are on rosters are usually the biggest trade chip. That, along with draft picks, is the normal base for a trade. Yet, when it comes to the MLB, prospects who haven’t played a single game in the big leagues are often what teams target.

This time around, the Philadelphia Phillies decided to lend a helping hand to the Los Angels on the house.

Mike Cisco wasn’t considered one of the Phillies’ most treasured assets from a prospect perspective. He was a decent reliever in Double-A as well as Triple-A but he wasn’t knocking anyone’s socks off. Still, the Angels believed they could tap into his hidden potential and not only got the Phillies to trade him to them in 2013 but they somehow found a way to get them to do it for nothing in return.

While Cisco never made the jump to the big leagues, the Phillies did them a huge favor by handing them a solid prospect for absolutely nothing in return.

Brad Mills (Photo by Rob Carr/Getty Images)
Brad Mills (Photo by Rob Carr/Getty Images) /

Wackiest MLB trade stories in league history: 19. $1 is all it takes

Sometimes, not every single part of a trade is made public. During a transaction between the Oakland A’s and the Milwaukee Brewers, that’s exactly what happened but nothing appeared out of the ordinary.

Brad Mills was destroying the competition as a member of the Nashville Sounds, a minor league affiliate of the Brewers. In 14 games with the club, Mills posted an ERA of 1.56. He quickly became the talking point of multiple trades. The A’s were able to pry him away but not without paying a heavy price.

Originally, it was announced that Mills was traded to the A’s for “cash considerations.” The hefty sum was then revealed to be one whole dollar. At first, it appeared as though the A’s were getting a steal of a player, however, Mills’ performance made them question whether or not he was worth that single buck. During his two years with the team, Mills registered an ERA over 5.00 and won only one game. He was seldom used as he spent the majority of his time glued to the bench.

While they won’t complain about spending that single dollar, at some point, they were probably thinking that they could have found a better way to use that money.

Cubs logo (Photo by B51/Mark Brown/Getty Images)
Cubs logo (Photo by B51/Mark Brown/Getty Images) /

Wackiest MLB trade stories in league history: 18. Quick change

Doubleheaders have always been a part of baseball history but none has ever been quite like this one.

In 1922, the St. Louis Cardinals took on the Chicago Cubs. Center fielder Cliff Heathcote struggled mightily with the Cardinals that season and that game in particular. He went 0-4 and the Cardinals went on to lose the game. Right field Max Flack, on the other hand, played a key role in the Cubs 4-1 win.

With Game 1 in the books, both managers decided to grab a bite to eat. What turned into harmless chit-chat, turned into a bizarre deal. Sometime in between meals, the pair agreed to a deal that would send Heathcote to the Cubs and Flack to the Cardinals. Unlike today, where a deal such as that wouldn’t allow those players to get on the field so suddenly, in the 1920s, it was no biggie.

In the second game of their doubleheaders, the two played for the opposing team. To add an even stranger twist to the story, both players simply swapped jerseys as there were no names on the back anyways and neither team had any extra jerseys around the dugouts.

New York Mets logo (Photo by Rich Schultz/Getty Images)
New York Mets logo (Photo by Rich Schultz/Getty Images) /

Wackiest MLB trade stories in league history: 17. All over the map

Joel Youngblood was ubiquitous one night.

For four seasons, the outfielder was a solid, yet not overwhelming contributor for the New York Mets. On August 4th, 1982, everything appeared normal. Youngblood started his day in Chicago rocking the blue and orange Mets colors.

It was an afternoon game and Youngblood was having himself a solid outing. He registered a two-run RBI for the away team and showed his value. Little did he know, however, the better he played, the more likely the Mets were going to deal him.

Although Youngblood began warming up for the next inning, he was immediately pulled from the lineup as he was traded to the Montreal Expos. Youngblood then gathered his things, said his goodbyes, dished out his hugs and headed to Philadelphia where his new team was playing the Phillies.

He may have just arrived on the scene but that didn’t stop manager Jim Fanning from calling him up to the plate in the sixth inning. Youngblood immediately produced, registering a single. It was the first and only time in MLB history that a player scored a hit for two different teams in different cities.

(Photo by Alexi Rosenfeld/Getty Images)
(Photo by Alexi Rosenfeld/Getty Images) /

Wackiest MLB trade stories in league history: 16. Dinner time

Johnny Jones wasn’t quite good enough to play in the major leagues. While he was a solid player overall, he never made the leap. Still, his trade story is about as weird as it gets.

In any league, trades typically take place between two organizations looking to get equal value for what they’re giving up. Normally, that means players that have some sort of value to said franchise. In this instance, none of that mattered.

In 1930, Jones was having his normal, yet underwhelming year for the Chattanooga Lookouts. Seemingly had enough of Jones and his subpar play, Joe Engel, head man of baseball operations for the Lookout, traded the up and down player to the Charlotte Hornets for a 25-pound turkey. Not only did Engel give up the shortstop for a live bird but in addition to that, he had it immediately fried and fed it to guests who attended the Southern Baseball Writers’ Association Dinner.

Jones continued his mediocre play in his new destination. As for the dinner, we’ve heard that several members went back for seconds.

(Photo by Meg Oliphant/Getty Images)
(Photo by Meg Oliphant/Getty Images) /

Wackiest MLB trade stories in league history: 15. Money and baseballs

Keith Comstock wasn’t overly impressive during his time with the Oakland Athletics but that didn’t stop other clubs from wanting him. Amongst them, was the Detroit Tigers.

With Comstock putting up fairly pedestrian numbers, the Athletics’ asking price wasn’t entirely high. Initially, Detroit offered to pay a flat fee of $100. Considering that their proposed trade came in the early 1980s, $100 simply wasn’t a large sum of money, especially when they weren’t adding a player to the mix.

While Comstock wasn’t a hot commodity, he was a decent player with upside. Unwilling to give up on their pursuit, the Tigers sweetened their offer and made it impossible for the Athletics to walk away. In addition to giving up $100, the Tigers also threw in a bag of baseballs.

For some reason, adding a bag of baseballs was enough to do the trick. The Tigers officially had their man. In hindsight, they might’ve overpaid, Comstock would only launch 14 homers during his entire six-year career.

Ernie Harwell (Photo by CARLOS OSORIO / AP POOL / AFP)
Ernie Harwell (Photo by CARLOS OSORIO / AP POOL / AFP) /

Wackiest MLB trade stories in league history: 14. Field help for booth help

So far, we’ve listed several unconventional trades that seem unlikely and downright impossible. To continue in that same theme, let’s introduce you to Ernie Harwell.

For a number of years, Harrell was the voice of the Atlanta Crackers of the Independent Southern Association. Harrell continually punched in early for work and left the building late. In short, he was terrific at calling games. To his credit, the Crackers weren’t the only team that noticed his dedication and admired it.

In 1948, Red Barber, the iconic voice of the Brooklyn Dodgers, suddenly passed away due to a bleeding ulcer. The franchise wanted a strong and reliable voice to replace him. Who better than Harrell? The Crackers were willing to part ways with him but only under one condition, the Dodgers fork over catcher Cliff Dapper. In a matter of moments, the deal was consummated and both teams walked away from their bizarre trade as happy as can be.

Harry Chiti (Photo by: Kidwiler Collection/Diamond Images/Getty Images)
Harry Chiti (Photo by: Kidwiler Collection/Diamond Images/Getty Images) /

Wackiest MLB trade stories in league history: 13. Back to square one

Harry Chiti wasn’t good enough to drag a team to championship contention. With that said, he was a solid overall piece that brought value to every franchise he played for. The New York Mets valued Chiti, possibly more than the team who had him in the Cleveland Indians.

In return for his services, the Mets promised to deliver the Indians a player that they would name later. In a weird turn of events, nothing went according to plan for the New York based team. They finished the season as the laughing stocks of the league as they compiled a record of 40-120-1.

After hitting a pathetic .195 in 15 games with the Mets, the franchise didn’t want any parts of Chiti any longer. So, remember that player the Mets agreed to send back to the Indians at a later date? Well, they made their decision. They sent back Harry Chiti.

Ironically enough, he never suited up for the Indians anyways. With his production so minuscule to say the least, Chiti was never seen on a professional baseball field ever again.

John McDonald (Photo by Thearon W. Henderson/Getty Images)
John McDonald (Photo by Thearon W. Henderson/Getty Images) /

Wackiest MLB trade stories in league history: 12. Same exact player

It was a case of deja vu. As previously mentioned in our last post, John McDonald was also shipped out for what turned out to be himself.

In 2005, the Toronto Blue Jays shortstop was having a terrific year. Although he wasn’t much of a home run hitter, registering 0 through 37 games, his overall numbers made plenty of teams value his contributions to winning. At the time, he batted .290, his on base percentage was the second best of his career with .340 and he drove in 16 runs.

The Detroit Tigers liked what they saw and immediately made the move to acquire him. In return, the franchise ensured the Blue Jays that they would ship out a player to be named later in return.

Once McDonald landed in his new home, everything went downhill. He continued to struggle with the long ball, registering 0 through 31 games. His overall numbers also cratered. His batting average fell from .290 with the Blue Jays to .260. His on base percentage also fell to .308. The Tigers would finish fourth in the AL Central with a record of 71-91.

With a decent sample size to take a look at, the Tigers were not impressed and shipped him back to where he came at the end of the year.

San Francisco Giants logo (Photo by Thearon W. Henderson/Getty Images)
San Francisco Giants logo (Photo by Thearon W. Henderson/Getty Images) /

Wackiest MLB trade stories in league history: 11. Not asking for much

John Odom dealt with plenty of personal issues off the field. He showed tremendous talent at a young age though. He was initially kicked off his high school baseball team but would find himself back on the diamond at Tallahassee Community College.

Odom made the most of his time there, racking up a record of 6-1 and an ERA of 2.75. He was ultimately drafted in 2003 by the San Francisco Giants. He never made it to the major leagues but he continually showed a ton of promise. Odom was eventually traded during his time in the minors to the Laredo Broncos but not for a player, draft picks or even cash.

No, Odom was shipped off for ten baseball bats worth $665. For some odd reason, the bats were never used in the first place. Instead, they sat in a locker collecting dust.

Seemingly amazed by the trade, Ripley’s Believe It or Not! took the bats off their hands for $10,000.

(Photo by Mark Rucker/Transcendental Graphics, Getty Images)
(Photo by Mark Rucker/Transcendental Graphics, Getty Images) /

Wackiest MLB trade stories in league history: 10. Boston Red Sox get Tris Speaker back for a bargain

It was an impressive career forged over 22 years of hard work in the majors. Tris Speaker is on the shortlist of greatest players to play the centerfield position. It’s been nearly 100 years since he’s swung a baseball bat on the professional level but he was impossibly great.

Reading off the statistics and accomplishments of Speaker is mind-boggling. He was an AL MVP, AL batting champ, his .345 batting average is good for ninth on the all-time list and he also has 3,514 career hits, good for fifth in history.

Yet, no matter how impressive he was, his career didn’t start off that way. In 1907, as a member of the Boston Americans, Speaker hit a pathetic .158 during the first handful of games in the season. The Americans, who became known as the Red Sox, sent Speaker to Little Rock’s Southern Association. All they wanted was the option to buy Speaker back for $500 if he developed. Well, he morphed into a great player.

During his time there, Speaker ultimately paid his own rent. Luckily for him, he turned into a Hall of Famer and the Red Sox were happy to have him on board.

Babe Ruth (Photo by Mark Rucker/Transcendental Graphics, Getty Images)
Babe Ruth (Photo by Mark Rucker/Transcendental Graphics, Getty Images) /

Wackiest MLB trade stories in league history: 9. Red Sox made a huge mistake

The argument can easily be made that Babe Ruth is the greatest player the game of baseball has ever seen. The numbers simply speak for themselves.

Not only was Ruth a major contributor of seven World Series titles but he was also a two-time AL MVP, two-time All-Star, a batting champion in 1924, and the ERA leader in 1916. In addition to that, he also has the third-most home runs in league history with 714, the second-most RBIs and he has the best slugging percentage in MLB history with .690.

To acquire a player of his stature, it would seemingly be impossible, or, it would take a king’s ransom. However, that simply wasn’t the case. Although Ruth had already contributed to three World Series wins, the Boston Red Sox allowed him to walk out the door to the New York Yankees for $125,000.

Now, what exactly did the Sox end up using the money on? Well, the ball club used the finances on the play, My Lady Friends. Ruth, of course, would go on to help the Yankees win four World Series. My Lady Friends, on the other hand, wasn’t that good.

Lefty Grove (Photo by Tommaso Boddi/Getty Images)
Lefty Grove (Photo by Tommaso Boddi/Getty Images) /

Wackiest MLB trade stories in league history: 8. Repairs needed

At this very moment, just about every Major League Baseball owner is a billionaire. Due to their financial status, it’s seldom that they ever complain about what’s needed around the ballpark. In the early 1920s however, it was a different story entirely.

Lefty Grove was once a minor league pitcher for the Martinsburg Mountaineers of the Blue Ridge League. While he showed a ton of promise, the Mountaineers decided he was expendable.

Earlier in the year, the city was hit by a vicious storm. One of the casualties of said storm was the Mountaineers outfield fence. While they could have easily paid $3,500 to get it fixed, they believed it made more sense to give up an asset. The ballclub traded Lefty Groves to the Baltimore Orioles for, you guessed it, $3,500. That money was then used to fix the outfield fence.

Groves would eventually find himself onto an MLB team in 1925 and he made the Mountaineers regret their decision. As a member of the Philadelphia Athletics and Boston Red Sox, he went on to lead the league in ERA nine separate times, took home a league MVP, was selected to six All-Star games and eventually, inducted into the Hall of Fame. We highly doubt the fence he was traded for had the same sort of impact.

Kerry Ligtenberg (Photo by JOHN ZICH/AFP via Getty Images)
Kerry Ligtenberg (Photo by JOHN ZICH/AFP via Getty Images) /

Wackiest MLB trade stories in league history: 7. $750 worth of junk

At times, Kerry Ligtenberg provided the Atlanta Braves with average production. But for the vast majority of his five years with the ball club, he was terrific.

On two separate occasions, Ligtenberg registered an ERA under 3.00. For long stretches, he was one of the better pitchers in the entire league. The end results were ultimately something that the Braves cherished but the franchise will always be thankful for the manner in which they acquired him.

For one of the better pitchers in franchise history, the Braves only forked over 12 dozen baseballs and two dozen bats to the Minneapolis Loons of the Independent North Central League. In total, the value of that baseball equipment equaled $750.

(Photo by Hugh Hastings/Getty Images)
(Photo by Hugh Hastings/Getty Images) /

Wackiest MLB trade stories in league history: 6. Oysters are too good to pass up

If you can remember Joe Martina, you have one helluva memory bank. He played one season in the major leagues with the Washington Senators and wasn’t exactly considered a star.

Although his time in the league was brief, he certainly made the most of it. Martina’s Senators took home the World Series in his lone season. For his part, Martina played fairly awful. He registered an ERA of 4.67 during the regular season and won only six games while losing eight.

The Senators viewed him as an inconsequential player as well, allowing him to pitch in only one game and one inning during their title run. So, with Martina’s shortcomings as a player on full display, it should come as no surprise what he was traded for. Martina was sent to New Orleans for two barrels of Oysters. Considering that he only lasted one season and never played a single inning in the majors, New Orleans probably regretted giving up those oysters.

(Photo by Igor Golovniov/SOPA Images/LightRocket via Getty Images)
(Photo by Igor Golovniov/SOPA Images/LightRocket via Getty Images) /

Wackiest MLB trade stories in league history: 5. Cleveland hoped for a return

During the 1994 MLB season, the Cleveland Indians were cruising through the league. They routinely ran through their opponents and put up a ton of runs in the process. Unfortunately for the Indians, their title dreams went by the wayside as the players ditched their helmets and bats and chose to strike over the insistence of a salary cap.

While the entire season and playoffs would be forever lost, the Indians held out hope that play would resume. During the strike, the Indians figured that it was the best time for them to solidify their ballclub. To do so, they traded for Hall of Fame right fielder, Dave Winfield from the Minnesota Twins for a player to be named later. But that’s where things got weird.

The ’94 strike stopped play for the rest of the year and Winfield was in the final year of his contract and chose to sign elsewhere in the offseason. So, with the Indians essentially getting a player for nothing in return, they attempted to make things right. While Minnesota wishes they got their hands on a valuable player, they ultimately settled on a nice dinner instead.

MLB logo (Photo by Mark Brown/Getty Images)
MLB logo (Photo by Mark Brown/Getty Images) /

Wackiest MLB trade stories in league history: 4. Easy transaction

No matter how hard he tried, pitcher Tim Fortugno was never able to become a reliable player in the major leagues. In total, he managed to rack up only three wins and even then, many would be incredulous that he has any at all. During his brief three-year career in the early/mid-1990s, Fortugno finished with an ERA of 5.06.

But while we’re highlighting his shortcomings on the baseball diamond, at one point, Fortugno had the potential to be a pretty good rotational piece. In 1989, the Brewers believed there was something there but they weren’t interested in giving up a whole lot to get him. Luckily for them, the Reno Silver Sox wasn’t very high on him anyways.

In order to pry him away, the Brewers simply had to cough up $2,500 in cash and throw in a bag of baseballs.

As mentioned previously, Fortugno wasn’t very good during his time in the majors and quickly flamed out. It’s unclear if he lasted longer than the baseballs that were traded away for him but it was close.

Doughnuts (Photo Illustration by Scott Olson/Getty Images)
Doughnuts (Photo Illustration by Scott Olson/Getty Images) /

Wackiest MLB trade stories in league history: 3. Who doesn’t love Doughnuts?

There’s no denying how bad Len Dondero was. His career lasted only 19 games in the majors and it’s easy to see why. Simply put, he wasn’t an impactful player in any way, shape or form.

During his single year with the St. Louis Browns in 1929, Dondero only managed to register six hits in 31 at bats. That in turn, resulted in a batting average of .194. His inability to locate the ball was only the start of his problems as indicated by his one career home run.

So, with his lack of production, his trade value was extremely low, maybe even lower than you think. In 1930, as a member of a San Antonio-based club in the Texas League, Dondero was traded to Dallas for a dozen donuts. With owner Homer Hammonds having a sweet tooth, it was an offer he simply couldn’t refuse.

Dondero didn’t provide his new ball club with much production but we were told the donuts were absolutely perfect.

Cy Young Award (Photo by Win McNamee/Getty Images)
Cy Young Award (Photo by Win McNamee/Getty Images) /

Wackiest MLB trade stories in league history: 2. A suit and some cash will get you the best pitcher

The Cy Young Award is undoubtedly the most coveted prize for any MLB pitcher. It symbolizes one thing and one thing only, sheer dominance from the position.

Although it’s been well over a century since his last appearance on the mound, Cy Young’s numbers still stack up favorably against just about every and anyone in the history of the game. Young’s 163.6 wins above replacement are currently third on the all-time list. His 749 complete games and 511 wins are also good for first on that list as well.

Yet, for as dominant as Young was, he was acquired by the Cleveland Spiders for $300 and a new suit.

To be fair, we need to add a bit of context to this scenario. In today’s day and age, $300 is barely enough for a phone bill but in 1890, it was worth approximately $9,000. While that’s significantly more than $300, that doesn’t appear to be nearly enough for a player who went on to not only have a Hall of Fame career but also one whose name is mentioned every year for an award that’s given out to the best pitchers in the game.

New York Yankees logo (Photo by Mark Brown/Getty Images)
New York Yankees logo (Photo by Mark Brown/Getty Images) /

Wackiest MLB trade stories in league history: 1. Change everything

Now we know, some of the trades on this list have been laughable and seemingly impossible to comprehend. With that said, this last one will take the cake as the wackiest trade of all time.

Fritz Peterson and Mike Kekich were both teammates on the New York Yankees. They were good friends during their time with the club and even lived nearby in New Jersey. The two would spend plenty of time with each other and brought their families along as well.

Peterson was an All-Star caliber player who dominated games. Kekich, on the other hand, spent most of his time on the bench, cheering teammates on. Still, that didn’t stop the two from sharing a close bond, maybe even too close.

Peterson began falling in love with Kekich’s wife and family. The feeling was mutual as Kekich had a particular fondness for Peterson’s loved ones. So, in an absolutely weird turn of events, both men decided to trade lives. They switched everything, they took their belongings and moved into the other’s house. From homes to wives to kids, they swapped everything.

Kekich and his new wife didn’t last long, however, and ended things shortly after. Peterson and his new wife, though, are still together.

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