![COVER-Weird-Sports-Trades---Ezra-Shaw]()
Anyone that has played in Fantasy Baseball or Fantasy Football leagues has likely witnessed some weird goings on in their leagues. Rumors of one owner trading the phone number of his hot sister to another owner for a middle infielder aren’t uncommon. Hearing that one guy loaned his backup kicker to his brother-in-law for one week because the latter loaned him $50 was something that might go down.
Usually, though, a good Fantasy League Commissioner will put the kibosh on such shenanigans, and all of those rumors end up just being that.
What’s strange is that Fantasy leagues try their best to replicate how a real major sports league works, from a commissioner to a draft to free agency and waivers to salary caps to just about anything else you can imagine.
Yet, we’re going to show you 13 major sports trades that would never be allowed in Fantasy leagues by any respectable commissioner.
13 Sports Trades Fantasy Commissioners Would Reject Immediately
There are plenty of weird trades from back in the day, like Babe Ruth being traded from the Red Sox to the Yankees for cash that was used to finance a play called, “No No Nanette.” And in recent years, there were trades of minor league baseball players for bags of baseballs or other equipment. Heck, there were even players traded for a “player to be named” that ended up being that same player! (See Harry Chiti and John McDonald.) But those are obvious no-nos. Most of the following trades had more to do with management, and many weren’t as much trades as they were penalties forced because of mischief.
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L.A. Clippers Traded 1st-Round Pick to Boston Celtics For Doc Rivers
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The Celtics’ glory days with Ray Allen, Kevin Garnett and Paul Pierce were over by 2013, and the C’s were going into rebuild mode. Head coach Doc Rivers was on his way out – so they traded him to the Clippers for a first-round pick!
In Rivers’ playing days, getting traded to the Clippers would have been a death knell, but instead, he inherited Chris Paul and Blake Griffin – not bad!
Photo Credit: Streeter Lecka, Getty Images
Rays Send All-Star Randy Winn to Mariners For Mgr. Lou Piniella
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Before Stu Sternberg, Andrew Friedman and Joe Maddon came to the Tampa area, the Devil Rays were a hot mess. In 2002, they traded their only good player, All-Star OF Randy Winn, to Seattle for hometown hero Lou Piniella, who would manage them to a 200-285 record for the next three years before having his contract bought out.
As a Rays fan, I’d like to just mention that Piniella stunk, and I believe he essentially mailed it in when he was sent to St. Pete. It’s like retirement started early.
Can you imagine in a keeper league, one team trading an outfielder to another team to have their co-owner switch teams? No.
Photo Credit: Bob Rosato, Getty Images
Jets Send 4 Draft Picks to Patriots For Parcells
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Ahhh, the Jets. They had to send four draft picks to the Patriots after some hiring shenanigans. Parcells left the Pats after losing the Super Bowl, and the Jets overcame some contract issues preventing them from hiring Parcells as a head coach. They signed Bill Belichick to be their head coach, with Parcells signed on as an “advisor.”
The NFL said, “Ummm, no.” And they awarded a third- and fourth-round pick, then a second-rounder the following year, and a first-rounder the year after that.
What’s funny is that Belichick ended up with the Patriots later, which means he would’ve benefited from those four players taken with those four draft picks! Unfortunately, the Pats fumbled those picks badly: RB Sedrick Shaw, G Damon Denson, WR Tony Simmons and LB Andy Katzenmoyer.
Photo Credit: New York Daily News Archive, Getty Images
Patriots Trade 2000 1st-Round Pick to Jets For Bill Belichick
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I still don’t really understand this one, other than knowing both Bill Parcells and Bill Belichick are prickly SOBs that love to leave teams standing at the altar. Parcells did it to the Bucs twice, and Belichick did it to the Jets in 2000. Belichick was supposed to take over for Parcells as the Jets head coach, but he bailed after agreeing to the deal, and got hired by the Patriots a month later. The Patriots had to trade a first-round pick to the Jets for those shenanigans.
It’s weird to think that two loser franchises, the Browns and Jets, lost out on chances to have the greatest coach in NFL history take them to the promised land.
Photo Credit: Icon Sports Wire, Getty Images
Jets Receive 4th-Round Pick From Chiefs For Herm Edwards
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The Jets – again! – let Herm Edwards out of his contract in 2006, so he could go coach the Chiefs. In return, K.C. sent the Jets a fourth-round pick – that turned out to be FSU RB Leon Washington.
In your Fantasy league, it would be like one bad keeper team taking over a mediocre keeper team. Meh.
Photo Credit: Joe Robbins, Getty Images
Tigers Trade Crappy Manager to Indians For Their Crappy Manager
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After some bad seasons at the helm of both the Detroit Tigers and Cleveland Indians baseball teams, the powers that be decided to trade their managers for each other. So in the late ‘50s, the Indians sent manager Joe Gordon after two seasons to the Tigers for their manager Jimmy Dykes, who coached a partial season in Motown the year before.
I can actually see this one going down in a Fantasy league someday. One Fantasy owner is griping at the bar about his horrible keepers to another Fantasy owner, who tries to one-up him about how bad his team is. So the two argue about who has the worse players until finally, after a lot of beer, they call the commissioner and tell him they want to trade entire teams. The commissioner, knowing how much work he’d be in store for, decide to just make one guy the manager of the other team, and vice-versa.
Jimmy Dykes Photo Credit: Bettmann, Getty Images
Twins Trade Dave Winfield to Indians For Dinner
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I love this one because it involves a Hall-of-Fame outfielder – and steaks.
Winfield was 40 years old when the Twins decided they needed to ship him off to Cleveland for a player to be named later in 1994. Then the season was canceled!
So Twins management decided to pick up the bill on an expensive steak dinner with Indians executives.
This is definitely something that has happened in some Fantasy leagues that probably shouldn’t have!
Photo Credit: Rich Pilling, Getty Images
Dodgers Trade Cliff Dapper to Brooklyn For Announcer Ernie Harwell
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The regular play-by-play announcer for the Brooklyn Dodgers in 1948 was sick, so they called up a hotshot with the Atlanta Crackers (seriously, how was a team named that?) named Ernie Harwell. The Crackers asked for and got a player in return, minor-league catcher Cliff Dapper. Harwell would go on to become a Hall-of-Famer, and Dapper – would not see another major-league at-bat.
In Fantasy Baseball leagues, this would be the equivalent of trading a backup catcher for the guy that served as your league’s auctioneer that spring.
Photo Credit: Kidwiler Collection, Getty Images
Buccaneers Trade 4 Early Draft Picks to Raiders For Jon Gruden
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Again, as a Tampa Bay fan, I liken this trade to the team selling its soul to the devil.
Tony Dungy was spinning his wheels with a stellar defense and a stalled offense, and the Bucs finally had to move on without him. After nearly getting Gators coach Steve Spurrier to wear pewter, they ended up making a deal with Raiders owner Al Davis for their head coach, Gruden. The Bucs sent two first-round picks, two second-round picks and $8 million for Chucky.
While that move certainly helped bring the Bucs a Super Bowl win after the 2002 season – it sunk it for the next decade.
Photo Credit: Al Messerschmidt, Getty Images
Marlins Send 2 Players to White Sox For Manager Ozzie Guillen
![]()
In an effort to really connect with both their Latin players and Latin fanbase in Miami, just in time for their new ballpark, the Marlins sent prospects Jhan Mariñez and Osvaldo Martínez to the White Sox. In the end, this move really made little difference to both ballclubs.
Photo Credit: Rich Pilling, Getty Images
Heat Send 1st-Round Pick and $1M to Knicks For Pat Riley
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Taking a page out of the NFL’s tampering compensation playbook, the Heat had to send their 1996 first-round pick to the Knicks because they signed Pat Riley to be their head coach and team president in 1995. Unfortunately, the league determined Miami talked with Riley while he was still under contract in New York.
Interestingly, that draft pick turned out to be Walter McCarty, who would play just one season in New York before getting traded to the Celtics. He went on to have a 10-year NBA career!
Photo Credit: Bill Baptist, Getty Images
Magic Trade 2nd-Round Pick to Heat For Stan Van Gundy
![]()
Riley was already done with Van Gundy in Miami, but the Heat still controlled his contract. So when SVG signed on to coach Dwight Howard and the Magic (after Billy Donovan balked), the Magic had to send a second-round pick to Miami.
The Heat replaced Stan Van Gundy with Stanko Barac – a Bosnian center. But they actually traded him to the Pacers (who nearly hired Van Gundy before the Magic did) that very same night. Barac later had his rights traded to the Mavericks in 2016 for Jeremy Evans, Emir Preldzic and cash considerations. Barac never played in the NBA, though.
It seems like every weird head coach trade deal in the NFL has the Jets involved, and in the NBA, the Heat are always involved.
I want to see a trade between the Heat and the Jets!
Photo Credit: Jonathan Daniel, Getty Images
Pirates Trade Manny Sanguillen to Oakland For Mgr. Chuck Tanner
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After just one year with the A’s as their manager, Oakland was ready to move on from him in 1977, so they shipped him to Pittsburgh in exchange for a solid hitting catcher in Manny Sanguillen.
The Bucs, of course, would go on to win the World Series in 1979 with the “We Are Family” Pirates, led by manager Chuck Tanner.
Photo Credit: Diamond Images, Getty Images
1/13
L.A. Clippers Traded 1st-Round Pick to Boston Celtics For Doc Rivers
The Celtics’ glory days with Ray Allen, Kevin Garnett and Paul Pierce were over by 2013, and the C’s were going into rebuild mode. Head coach Doc Rivers was on his way out – so they traded him to the Clippers for a first-round pick!
In Rivers’ playing days, getting traded to the Clippers would have been a death knell, but instead, he inherited Chris Paul and Blake Griffin – not bad!
Photo Credit: Streeter Lecka, Getty Images
2/13
Rays Send All-Star Randy Winn to Mariners For Mgr. Lou Piniella
Before Stu Sternberg, Andrew Friedman and Joe Maddon came to the Tampa area, the Devil Rays were a hot mess. In 2002, they traded their only good player, All-Star OF Randy Winn, to Seattle for hometown hero Lou Piniella, who would manage them to a 200-285 record for the next three years before having his contract bought out.
As a Rays fan, I’d like to just mention that Piniella stunk, and I believe he essentially mailed it in when he was sent to St. Pete. It’s like retirement started early.
Can you imagine in a keeper league, one team trading an outfielder to another team to have their co-owner switch teams? No.
Photo Credit: Bob Rosato, Getty Images
3/13
Jets Send 4 Draft Picks to Patriots For Parcells
Ahhh, the Jets. They had to send four draft picks to the Patriots after some hiring shenanigans. Parcells left the Pats after losing the Super Bowl, and the Jets overcame some contract issues preventing them from hiring Parcells as a head coach. They signed Bill Belichick to be their head coach, with Parcells signed on as an “advisor.”
The NFL said, “Ummm, no.” And they awarded a third- and fourth-round pick, then a second-rounder the following year, and a first-rounder the year after that.
What’s funny is that Belichick ended up with the Patriots later, which means he would’ve benefited from those four players taken with those four draft picks! Unfortunately, the Pats fumbled those picks badly: RB Sedrick Shaw, G Damon Denson, WR Tony Simmons and LB Andy Katzenmoyer.
Photo Credit: New York Daily News Archive, Getty Images
4/13
Patriots Trade 2000 1st-Round Pick to Jets For Bill Belichick
I still don’t really understand this one, other than knowing both Bill Parcells and Bill Belichick are prickly SOBs that love to leave teams standing at the altar. Parcells did it to the Bucs twice, and Belichick did it to the Jets in 2000. Belichick was supposed to take over for Parcells as the Jets head coach, but he bailed after agreeing to the deal, and got hired by the Patriots a month later. The Patriots had to trade a first-round pick to the Jets for those shenanigans.
It’s weird to think that two loser franchises, the Browns and Jets, lost out on chances to have the greatest coach in NFL history take them to the promised land.
Photo Credit: Icon Sports Wire, Getty Images
5/13
Jets Receive 4th-Round Pick From Chiefs For Herm Edwards
The Jets – again! – let Herm Edwards out of his contract in 2006, so he could go coach the Chiefs. In return, K.C. sent the Jets a fourth-round pick – that turned out to be FSU RB Leon Washington.
In your Fantasy league, it would be like one bad keeper team taking over a mediocre keeper team. Meh.
Photo Credit: Joe Robbins, Getty Images
6/13
Tigers Trade Crappy Manager to Indians For Their Crappy Manager
After some bad seasons at the helm of both the Detroit Tigers and Cleveland Indians baseball teams, the powers that be decided to trade their managers for each other. So in the late ‘50s, the Indians sent manager Joe Gordon after two seasons to the Tigers for their manager Jimmy Dykes, who coached a partial season in Motown the year before.
I can actually see this one going down in a Fantasy league someday. One Fantasy owner is griping at the bar about his horrible keepers to another Fantasy owner, who tries to one-up him about how bad his team is. So the two argue about who has the worse players until finally, after a lot of beer, they call the commissioner and tell him they want to trade entire teams. The commissioner, knowing how much work he’d be in store for, decide to just make one guy the manager of the other team, and vice-versa.
Jimmy Dykes Photo Credit: Bettmann, Getty Images
7/13
Twins Trade Dave Winfield to Indians For Dinner
I love this one because it involves a Hall-of-Fame outfielder – and steaks.
Winfield was 40 years old when the Twins decided they needed to ship him off to Cleveland for a player to be named later in 1994. Then the season was canceled!
So Twins management decided to pick up the bill on an expensive steak dinner with Indians executives.
This is definitely something that has happened in some Fantasy leagues that probably shouldn’t have!
Photo Credit: Rich Pilling, Getty Images
8/13
Dodgers Trade Cliff Dapper to Brooklyn For Announcer Ernie Harwell
The regular play-by-play announcer for the Brooklyn Dodgers in 1948 was sick, so they called up a hotshot with the Atlanta Crackers (seriously, how was a team named that?) named Ernie Harwell. The Crackers asked for and got a player in return, minor-league catcher Cliff Dapper. Harwell would go on to become a Hall-of-Famer, and Dapper – would not see another major-league at-bat.
In Fantasy Baseball leagues, this would be the equivalent of trading a backup catcher for the guy that served as your league’s auctioneer that spring.
Photo Credit: Kidwiler Collection, Getty Images
9/13
Buccaneers Trade 4 Early Draft Picks to Raiders For Jon Gruden
Again, as a Tampa Bay fan, I liken this trade to the team selling its soul to the devil.
Tony Dungy was spinning his wheels with a stellar defense and a stalled offense, and the Bucs finally had to move on without him. After nearly getting Gators coach Steve Spurrier to wear pewter, they ended up making a deal with Raiders owner Al Davis for their head coach, Gruden. The Bucs sent two first-round picks, two second-round picks and $8 million for Chucky.
While that move certainly helped bring the Bucs a Super Bowl win after the 2002 season – it sunk it for the next decade.
Photo Credit: Al Messerschmidt, Getty Images
10/13
Marlins Send 2 Players to White Sox For Manager Ozzie Guillen
In an effort to really connect with both their Latin players and Latin fanbase in Miami, just in time for their new ballpark, the Marlins sent prospects Jhan Mariñez and Osvaldo Martínez to the White Sox. In the end, this move really made little difference to both ballclubs.
Photo Credit: Rich Pilling, Getty Images
11/13
Heat Send 1st-Round Pick and $1M to Knicks For Pat Riley
Taking a page out of the NFL’s tampering compensation playbook, the Heat had to send their 1996 first-round pick to the Knicks because they signed Pat Riley to be their head coach and team president in 1995. Unfortunately, the league determined Miami talked with Riley while he was still under contract in New York.
Interestingly, that draft pick turned out to be Walter McCarty, who would play just one season in New York before getting traded to the Celtics. He went on to have a 10-year NBA career!
Photo Credit: Bill Baptist, Getty Images
12/13
Magic Trade 2nd-Round Pick to Heat For Stan Van Gundy
Riley was already done with Van Gundy in Miami, but the Heat still controlled his contract. So when SVG signed on to coach Dwight Howard and the Magic (after Billy Donovan balked), the Magic had to send a second-round pick to Miami.
The Heat replaced Stan Van Gundy with Stanko Barac – a Bosnian center. But they actually traded him to the Pacers (who nearly hired Van Gundy before the Magic did) that very same night. Barac later had his rights traded to the Mavericks in 2016 for Jeremy Evans, Emir Preldzic and cash considerations. Barac never played in the NBA, though.
It seems like every weird head coach trade deal in the NFL has the Jets involved, and in the NBA, the Heat are always involved.
I want to see a trade between the Heat and the Jets!
Photo Credit: Jonathan Daniel, Getty Images
13/13
Pirates Trade Manny Sanguillen to Oakland For Mgr. Chuck Tanner
After just one year with the A’s as their manager, Oakland was ready to move on from him in 1977, so they shipped him to Pittsburgh in exchange for a solid hitting catcher in Manny Sanguillen.
The Bucs, of course, would go on to win the World Series in 1979 with the “We Are Family” Pirates, led by manager Chuck Tanner.
Photo Credit: Diamond Images, Getty Images
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