Top 10 Most Bizarre Trades in Sports History (AKA Actual “Bag of Pucks” Deals)

Weird Trades in Sports

Some trades are just bad. Some are lopsided. But a special few are so weird, so WTF, (We're allowed to say Fuck at HeyRookie, but we won't) that they deserve a spot in sports lore — right next to the phrase “we’ll trade him for a bag of pucks.”

Here are 10 real trades that actually happened — ranked by pure, unfiltered absurdity.

10. Kyle Lowry’s Bizarre Trade Equals Long Road to a Broken Copier (NBA)

In 2009, the Memphis Grizzlies traded Kyle Lowry to the Houston Rockets. Years later, through a bizarre chain of pick swaps, the draft rights tied to that deal ended up with Minnesota… who used them on Luke Babbitt… who was flipped for Martell Webster… who was later dealt for a used office copier that didn’t even work. The entire transaction tree of a future NBA champion ended with a busted printer in a janitor’s closet. Lowry > Lexmark, apparently.

9. Keith Comstock for a Bucket of Balls (MLB)

Minor league pitcher Keith Comstock was traded in the early ‘80s by the A’s to the Tigers for a bucket of baseballs. Seriously. Not metaphorically — literally a bucket of balls. Comstock later joked, “They were new balls, at least.” Still, no +EV there.

8. Tom Martin for a Used Bus (WHL Hockey)

In 1983, the WHL’s Seattle Breakers needed a team bus. The Victoria Cougars had one. So the two teams made a deal: Victoria sends over the bus, and Seattle sends winger Tom Martin. Martin later became known as “Bussey,” which sounds like a minor league insult but is 100% factual.

7. Harry Chiti for… Harry Chiti (MLB)

The ultimate circular deal. In 1962, the Mets acquired catcher Harry Chiti from the Reds for a “player to be named later.”

After a rough few weeks, the Mets sent Chiti back to the Reds — as the player to be named later. Chiti became the first MLB player traded for himself.

That’s not even a metaphor. That’s baseball in its most existential form.

6. Dave Winfield for Dinner (MLB)

1994 was a mess. The strike-shortened season left Dave Winfield technically still with the Twins, but he hadn’t played. The Indians traded for him in case play resumed. It didn’t.

Rather than send players or picks, Cleveland just… bought the Twins front office a nice dinner. That was the trade. “You take the Hall of Famer, we’ll take the filet mignon.”

5. Bill Belichick: Traded Coach (NFL)

The Hoodie once wore green — briefly. In 2000, the Jets named Bill Belichick head coach. One day later, he quit by writing “I resign as HC of the NYJ” on a napkin.

The Patriots scooped him up, but to get him, they had to trade a first-round pick to the Jets… for a coach who never coached a game there.

Belichick then went on to win six Super Bowls. The Jets, well… you know.

4. John McDonald Traded for Himself (MLB)

In 2005, the Blue Jays traded John McDonald to the Tigers for “future considerations.” Later that year, the Tigers returned the favour — and the player.

Yup. McDonald was the “future consideration.” Basically: “We’ll borrow him for the summer and send him back.” It’s like lending your neighbour your lawnmower and getting it returned with the same gas tank.

3. The Cash Consideration That Became Jordan Clarkson (NBA)

In 2014, the Washington Wizards sold their second-round pick to the Lakers for cash considerations. The Lakers used that pick to draft Jordan Clarkson, who went on to become an NBA Sixth Man of the Year.

Washington, on the other hand, got about $1.8 million, which reportedly helped cover luxury tax penalties. They bought nothing… and paid extra for it.

2. Gretzky for Cash, Picks, and Tears (NHL)

Wayne Gretzky, in his absolute prime, was traded from Edmonton to LA for picks, players, and $15 million in cold, hard cash. It wasn’t a hockey decision — it was a business one. The Oilers didn’t just trade The Great One. They traded the soul of a nation, but still won every fucking draft lottery they had a chance to, but have lost back to back Cup Finals, Karma exists even to those who believe in McJesus.

1. Ted Stepien: The NBA’s Rule-Changing Madman (NBA)

Cavs owner Ted Stepien was so epically bad at making trades in the early ‘80s that the NBA had to create a rule to stop him.

He kept dumping future first-round picks like they were scratch tickets, often for random veterans who didn’t stay on the roster. The league finally said: enough. The Stepien Rule now bans teams from trading first-rounders in back-to-back years. When your trading style literally changes the rulebook? You’ve hit Hall of Shame levels.

Sports are unpredictable. But this? This is chaos in paperwork form.

One man's all-star is another man's broken copier, dinner tab, or bucket of balls.