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Craziest Sports Trades Ever – 21 Wild Deals Involving the Biggest Stars

| October 22, 2020 6:07 am PDT
21 Crazy Sports Trades That Shook Us to Our Core

Sports are largely built on the idea that a team can come together and accomplish anything. Great coaching can even take subpar talent, rally the troops, and push unlikely champions to the top.

But when things don’t go the desired route, trades happen. Whether it be the team loses, the player is a distraction, or the player demands more money, sometimes the only option is to move on.

Trades have become commonplace in a world of free agency, as the financial aspect often decides things for franchises. But despite it being a regular occurrence, there’s always been an unspoken agreement that some players are untouchable.

History proves that’s simply not the case, and there are some crazy sports trades that shook us to our core.

Sports trades can open the door to a team having newfound hope in winning a title. They can win you money on the top sports betting sites if you see them coming. And they can also break your heart.

Here are the craziest sports trades ever that no fan will soon forget (or probably needs to be reminded of).

Boston Trades Babe Ruth to New York (1920)

It happened back in 1920, but the trade of Babe Ruth from the Boston Red Sox to the New York Yankees still stands as one of the craziest sports trades ever.

Looking back, the deal was of the catastrophic variety. Boston owner Harry Frazee decided to sell Babe Ruth to the hated Yanks for a whopping $100,000.

That was big money at the time, but Boston got zero players for The Bambino, which is especially infuriating when you consider how good he was at hitting and pitching.

It’s safe to say the Yankees got a steal.

Ruth clobbered 54 home runs in his first season with the team and helped them get to seven World Series (winning three). Boston, meanwhile, endured a curse that kept them from winning a title until 2004.

Babe Ruth

Wilt Gets Traded Again…to Lakers (1968)

Wilt Chamberlain is one of the best NBA players in league history and holds numerous records that will never be broken. One is his infamous 100-point game.

That’s why it’s quite shocking that he ever got traded. It’s even more shocking that he got dealt twice.

The first trade saw the Warriors send Wilt to the 76ers. That trade was big enough, but it’s the one that brought him to the Lake Show that everyone remembers.

First, because it was the last time he was traded. But also because it led to four NBA Finals appearances and one championship.

It also was the first time a reigning NBA MVP was traded the year after winning the award. The official deal landed Wilt in Hollywood and brought back Darrall Imhoff, Jerry Chambers, and Archie Clark to the Sixers.

Bucks Hand Kareem to Lakers (1975)

This one isn’t totally fair to criticize, as it’s been known for some time that Kareem Abdul-Jabbar wanted out of Milwaukee for a variety of reasons.

Kareem was responsible for Milwaukee’s lone NBA championship, but the team wasn’t winning anymore and was too small of a market. Abdul-Jabbar’s exit was written on the proverbial wall, yet the Bucks still got reasonable value for him in a trade with the Lakers.

LA handed the Bucks Elmore Smith, Brian Winters, and two draft picks in the 1975 NBA Draft.

That deal didn’t lead to much for Milwaukee, while the Lakers secured five more titles with Lou Alcindor on their roster. The Lakers and Kareem won, and this was a wild trade, but it actually was one that was unavoidable.

Sixers Steal Dr. J From the Nets (1976)

One year later, another shocking NBA trade went down when the Nets dealt superstar scorer Julius Erving to the Philadelphia 76ers.

Better known as Dr. J, Erving was one of the NBA’s best scorers, having averaged 29.3 points per game prior to being traded.

What’s even crazier is the Nets were dominating with Dr. J on hand, as they had just won the 1976 ABA title. The merger with the NBA arrived, however, and financial concerns had the Nets looking to deal their beloved star.

The deal amounted to $3 million for Erving and another $3 million to account for the Nets’ expansion fee. Dr. J went on to have a storied career with the Sixers, helping them reach the NBA Finals four times and securing the franchise’s last title in 1983.

The Nets, meanwhile, never recovered from the deal and have yet to win a title in the NBA.

John Elway Calls the Shots (1983)

There have been a few big trades involving professional athletes before they ever even played. Eric Lindros and Eli Manning also come to mind, but the most iconic trade of this kind came thanks to John Elway.

The Stanford star was originally drafted by the Baltimore Colts, but Elway emphatically declined to ever play for the franchise. The Colts opted to call his bluff and take him with the first overall pick in the 1983 NFL Draft, only to realize Elway wasn’t joking.

With Elway using a realistic threat of playing professional baseball instead of suiting up for Baltimore, the Colts dealt him to the Denver Broncos.

The deal sent Elway to the only NFL team he’d ever play for — one he’d reach the Super Bowl with five different times, while winning two.

Baltimore brought back Chris Hinton, Mark Herrman, and a future first-round pick in the deal but failed to land a franchise passer. It wasn’t until they landed Peyton Manning in the 1998 draft that they truly recovered from Elway’s act of defiance.

Even The Great One Gets Traded (1988)

You know literally anybody can get traded when even Wayne Gretzky isn’t untouchable.

The Michael Jordan of hockey, the man dubbed The Great One was shipped to the Los Angeles Kings in a wild 1988 deal coined “The Trade.”

This wasn’t an ordinary trade, of course, as Edmonton Oilers owner Peter Pocklington needed money and as part of the deal, secured $15 million to send Gretzky (as well as teammates Marty McSorley and Mike Krushelnyski) out of town.

Gretzky had more than proven his worth as an NHL star to that point, as he scored 583 goals and won four Stanley Cup titles with the Oilers.

Following the trade, Edmonton won just one more championship and suffered through years of not even being competitive. Gretzky continued a career of greatness, as he broke records and went down as the best hockey player of all time.

Wayne Gretzky

The Vikings Overpay for Herschel Walker (1989)

One of the most famous trades in history is also probably the craziest NFL trade we’ve ever seen.

Herschel Walker should be known for his amazing college career at Georgia or even his hot start with the Dallas Cowboys. After rushing for 1,514 yards in 1988, Walker’s value was at its highest point, and Dallas cashed in.

The Minnesota Vikings offered a king’s ransom for a 27-year-old Walker, which also involved the San Diego Chargers and included 18 players and draft picks, making it the biggest NFL trade ever.

Dallas received Jesse Solomon, David Howard, Isaac Holt, and Alex Stewart in the deal, along with eight proposed draft picks. Minnesota received Walker and four picks, while the Chargers brought back running back Darrin Nelson in the deal.

On the surface, the Vikings made a last-ditch effort to make a title run. That wouldn’t come to fruition, however, while the Cowboys turned this massive trade into Emmitt Smith, Russell Maryland, and Darren Woodson.

Dallas went on to win three Super Bowls following the trade. Vikings fans are still shaking their heads.

The Saints Go All-In on Ricky Williams (1999)

One of the most lopsided trades in sports history saw Mike Ditka and the New Orleans Saints go all-in on Texas running back Ricky Williams.

Easily the best running back in college football going into the 1999 NFL Draft, Williams was a threat to go very early and wasn’t a prospect the Saints could realistically get.

That’s why Ditka got desperate/creative and packaged all of his team’s picks in a deal to land the top pick in the draft. In all, Ditka sent eight draft picks to the Washington Redskins, who hilariously turned the haul into a whole lot of nothing.

New Orleans overpaid for Williams, however, as the Saints struggled during his rookie year and eventually saw Ditka get fired. Williams was productive enough but lasted just three years in New Orleans before moving on to the Miami Dolphins.

Ricky Williams and Mike Ditka

The Mariners Give The Kid to the Reds (2000)

The Seattle Mariners can’t be raked over the coals for this one. It’s been made known that Ken Griffey Jr., who was entering the final year of his contract, wanted out.

Playing for the Reds was always on Griffey’s wish-list (his dad played nine years in Cincinnati), and had the Mariners not moved him, he could have left for nothing as a free agent.

Still, trading perhaps the best baseball player at the time was still shocking. Griffey Jr. was cranking home runs out of the park at an alarming rate, was as marketable as anyone, and had baseball’s “perfect” swing.

But The Kid was done in Seattle and wanted to move on. Even so, the return wasn’t great for the Mariners, who brought back Jake Meyer, Antonio Perez, Brett Tomko, and Mike Cameron.

None of those names came close to matching the impact Ken Griffey Jr. had in Seattle, but it’s unrealistic that anyone ever expected to.

For what it’s worth, Griffey looked like a smart get by the Reds for precisely one year. The Kid smacked 40 homers in his first year with the team in 2000 but topped 30 home runs just three times in his nine years with the club.

Cincinnati never benefited from the trade in the win column, either, as the franchise made the playoffs zero times with The Kid in Ohio.

The Pinstripes Secure A-Rod (2004)

There have been some crazy MLB trades over time, but one of the zaniest ever came in 2004 when the New York Yankees acquired A-Rod.

The Alex Rodriguez trade is wild for three reasons — the guy had signed a disgustingly large contract with the Texas Rangers just a few years earlier, the rich got richer, and it included another superstar power hitter.

Afonso Soriano didn’t possess the star power A-Rod did, but the guy still clocked 421 home runs in a brilliant career. The star swap was one thing, but the Yanks also took on a massive contract in their plight to return to glory.

New York was already close, too. The Yanks had lost two World Series in the previous three years and were trying to rebuild a dynasty that had secured championships in 1996, 1998, 1999, and 2000.

Rodriguez was viewed by many as the missing link. While the goal wasn’t met instantly, A-Rod still played a hand in eight playoff runs and a 2009 World Series title.

Texas, meanwhile, got out of a crazy contract, got 64 homers out of Soriano in the next two years, and eventually reached the World Series in 2010 and 2011.

Lakers Pick Kobe Over Shaq (2004)

All good things must come to an end. That old homage rings true for the Lakers, who seem to have a hand in every major sports trade in history.

To their credit, Los Angeles was as good as anyone at acquiring elite talent and knowing when to move on. Back in 2006, they apparently could see that keeping Shaquille O’Neal and Kobe Bryant together wasn’t going to lead to more championships.

The two had an ongoing feud, and with Bryant wrapped up in sexual assault allegations (and also looking to secure a long-term deal), the franchise had to pick a side.

Despite reaching the NBA Finals the year prior (and winning three titles together), the Shaq and Kobe feud reached a boiling point and forced the Lakers’ hand.

Los Angeles chose to side with the younger Kobe.

The team sent Shaq to the Miami Heat for a reasonable haul, getting Bryant some legit role players in Lamar Odom, Caron Butler, Brian Grant, and a future first-round pick.

It looked like a gutting of Miami, but the Heat actually went on to win the NBA Finals in 2006.

The trade also ended up working out for the Lake Show, as Bryant secured three more championships once the Lakers made another big move (more on that in a bit).

Randy Moss Sent Packing to Oakland (2005)

This is another big NFL trade that didn’t result to much but was still positively nuts.

Randy Moss has gone down as perhaps the most dominant wide receiver in NFL history, and prior to being dealt by the Vikings, he had put up 13 touchdowns in just 13 games in 2004.

A year before that, he scored 17 touchdowns for the second time in his career.

Very much in his prime at the time of this deal, Moss was shipped out of town more because of his bad attitude than his skill-set. Oakland gave up linebacker Napoleon Harris and their first-round pick for that year.

That was actually fairly good compensation for a diva receiver, but considering Moss really only had a handful of elite seasons following this trade (and never won a title elsewhere), the Vikings shouldn’t be too bummed.

The players they received in the deal never came close to matching the value Moss offered, but the point is the aftershock of this trade, not the pieces involved.

Moss would later be moved to the Patriots, which delivered a record-setting season and nearly led to a championship. This first trade was much more shocking at the time, however.

The Fish Send Miggy to Detroit (2007)

One of the loudest MLB trades in league history arrived in 2007 when the at-the-time Florida Marlins sent masher Miguel Cabrera (and Dontrelle Willis) to the Detroit Tigers.

The deal included a whopping six prospects for the Marlins, while Detroit added a rising power hitter that also was a patient menace at the plate.

It’s hard to say it wasn’t a good deal for Detroit, either. Already a World Series threat, the Tigers made their way through a few playoff misses to give it one more go at a title in 2012.

Adding Miggy didn’t produce a championship but almost counts for something. Florida, meanwhile, gave up one of the greatest talents of the era and really only got back Andrew Miller in return.

He was the best prospect in the deal, although he really never delivered in his time with the Marlins.

Packers Trade Brett Favre to Jets (2008)

This one wasn’t crazy due to some huge haul the Green Bay Packers got for jettisoning Brett Favre to the skies. Few teams were about to pay up for a 38-year-old quarterback with an affinity for interceptions, after all.

Still, Favre had tortured the Packers for years with his retirement flirtation, and when he finally seemed to go away for good, his surprise return threatened to derail the start of the Aaron Rodgers era.

Not keen on that happening, Green Bay was ready to move on and surprised the NFL world when they swung a trade that sent Favre to the New York Jets.

It didn’t take much, as Gang Green only had to give up a conditional pick to make the deal happen. It could have escalated to a first-rounder had the Jets made the playoffs, and they very nearly did just that after an 8-3 start.

The trade never amounted to anything, of course, as Favre bolted for Minnesota the following year.

That said, it was a huge moment in NFL history, and it also gave way to the Aaron Rodgers era, which has arguably been as good (or better) as anything Favre delivered.

It’s Just Manny Being Traded (2008)

Manny Ramirez finally talked his way out of town in 2008 when the Boston Red Sox shipped him to the Dodgers in a wild three-team trade.

It was a pretty big deal considering Ramirez had been one of Boston’s biggest stars, having crushed 274 homers in his eight years with the team.

Ramirez helped Boston buck their curse (see: Ruth, Babe) and returned the Red Sox to glory, guiding them to two World Series titles.

Things went sour after that, however. Ramirez detailed a frayed relationship upon his exit.

“The Red Sox don’t deserve a player like me…I’ve seen how they mistreated other great players when they didn’t want them to try to turn the fans against them.”

Every good run comes to an end eventually, however, and the Red Sox booted Ramirez and his antics to LA, in return for Jason Bay.

Pau Gasol Helps Lakers Rebuild on the Fly (2008)

The Lakers are on this list for what feels like the millionth time, but that just shows their dedication to landing star power and competing for titles.

Following the Shaq trade, LA didn’t find the success they desired, and a trade for a new big man was deemed necessary. That’s when the team turned its sights on landing Memphis Grizzlies star forward Pau Gasol.

Gasol was firmly establishing himself as one of the best big men in the NBA, as he was a footwork maven down low and was fresh off of a 20.8 and 9.8 season.

An elite rebounder, scorer, and maturing floor spacer, Gasol was precisely what Kobe Bryant needed to get the Lakers back to the Finals.

It was a massive splash move at the time, as Gasol came to Hollywood in a deal involving his brother (Marc), Kwame Browns, Javaris Crittenton, Aaron McKie, and two future first-round picks.

LA easily won this deal with three more championship runs, but it’s hard to say the Grizzlies made a poor choice. They discovered a gem in Marc Gasol and quietly built a very strong playoff threat for the next decade.

The Celtics Make a Champion With KG (2009)

Kevin Garnett did all he could to make the Minnesota Timberwolves title contenders. Minnesota couldn’t surround him with a viable supporting cast, though, and eventually felt forced into a trade.

The Big Ticket actually brought back a pretty good haul, as the Celtics gave the T’Wolves Al Jefferson, Sebastian Telfair, Gerald Green, Theo Ratliff, and draft picks to facilitate the deal.

Jefferson was a 20-and-10 stud, while the prospects were intriguing gets at the time. It didn’t accumulate to anything of substance for Minnesota, though, while landing KG instantly vaulted Boston into title contention.

The Celtics won the NBA Finals the year they acquired Garnett and got back to one more Finals two years later. In all, Garnett lasted six seasons in Boston, helping the Celtics get to the ECF or further three different times.

Kevin Garnett Celtics

OKC Gives Up James Harden (2012)

The compensation isn’t wild here, but the fact that the Thunder traded away one of their best players the year after reaching the NBA Finals does make this crazy.

All because of money.

OKC couldn’t (or wouldn’t) figure out a long-term deal with bench spark James Harden, so the Thunder swung a deal with the Houston Rockets.

They didn’t have much of a choice but still got a decent haul in Kevin Martin, Jeremy Lamb, and two first-round picks.

None of it amounted to much, nor did the fact that Harden morphed into a superstar (not to mention one of the best scorers ever) ease the pain.

In summary, the Rockets scored one of the league’s brightest stars for a small package, while the Thunder turned down a shot at a title because of money.

Bears Snag Khalil Mack From Raiders (2018)

The Chicago Bears believed they were one major addition from contending for a Super Bowl in 2018.

They weren’t exactly wrong, as the acquisition of pass rusher Khalil Mack provided a huge boost to an already strong defense and helped the Bears go 12-4.

Chicago won the NFC North and returned to the playoffs, but landing Mack and getting back to postseason play didn’t come without a price.

The blockbuster deal sent four draft picks in total to the Oakland Raiders, which continued Jon Gruden’s on-the-fly dismantling of the roster he took over.

The Bears looked like geniuses at the time, and it’s hard to fault them for the deal, but they gave up some serious draft capital and weren’t able to turn the move into a championship.

The Brow Heads to the Lake Show (2019)

One of the biggest NBA trades ever involved the Lakers, when they went over and beyond in their efforts to acquire Pelicans star big man Anthony Davis.

A potential pairing with NBA legend LeBron James created incentive for Davis, who before long informed New Orleans that he would not be re-signing with the team and desired a trade.

The Pelicans sought numerous trade partners but ultimately chose a deal with the Lake Show due to their influx of young talent. Ultimately, the deal sent The Brow to the Lakers for Lonzo Ball, Brandon Ingram, Josh Hart, and three first-round draft picks.

Davis instantly helped turn the Lakers back into title contenders, while the Pelicans used LA’s lottery pick in that year to draft Duke sensation Zion Williamson.

Nuk Lands in the Desert (2020)

The legacy of Houston Texans head coach and GM Bill O’Brien will forever be attached to the trade of DeAndre Hopkins.

O’Brien would be mildly vindicated eventually once news broke that the man known as Nuk desired a pay increase, but trading away Houston’s top offensive weapon still felt bold.

It was even crazier that the Texans brought back a seemingly washed-up running back in David Johnson to make the deal happen.

Coming off of a huge 100+ catch campaign and regarded as one of the game’s best wide receivers, the DeAndre Hopkins trade looks laughable on Houston’s part.

What Was the Craziest Trade in Sports History?

Some trades were about money. Others were one-sided. A handful were fair for all parties involved. There were many that involved an insane amount of drama and others that were purely business.

On one side of the deal, there was the end of an era and a franchise being crushed. On the other, a dawn of new possibilities that would give way to championships.

Of the lot, the craziest sports trade of all time is arguably the Ricky Williams trade. I could go with a bigger name, a more iconic deal, or one that really had an impact on championships.

But how do you beat trading your entire allotment of draft picks (plus future picks) to trade up for the #1 pick to select a running back? And then this blows up in your face so much that the head coach gets canned and said player lasts just two more years with the team?

Any trade detailed above could be the worst (best?) or craziest trade ever, but it’s hard to top the Ricky Williams trade.
Noah Davis
Noah Davis

Noah Davis is one of the more diverse writers at GamblingSites.com. Like many of his colleagues, he's a huge fan of both football and basketball. But he also writes about box office records, TV show prop bets, DFS, and all kinds of other subjects.

When it comes to the NFL, Noah's favorite team is the Cleveland Browns. He enjoys cheering them on with his wife and daughter.

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