Exploring the Biggest What-If Trades That Never Happened

30 January 2026

Sports are filled with moments that make us stop and think, “What if?” But few questions trigger a fan's imagination more than blockbuster trades that were this close to happening — and then never did. You know the ones… those deals whispered about in locker rooms and front offices, only to be shut down at the last second. The sliding doors moments of sports history.

And let’s be real — as fans, we live for that drama. We think about how different everything would be if that one trade had gone through. Championships could swing, dynasties could crumble, and careers? Totally rewritten.

So grab a snack, kick back, and let’s dive into some of the juiciest, most mind-blowing what-if trades that almost happened in sports history — but didn’t.

NBA: The Almost-Kobe-to-Chicago Trade

Let’s kick things off with one of the biggest what-if trades in NBA history. Back in 2007, the late, great Kobe Bryant was frustrated with the Lakers. He wasn’t shy about it either — he wanted out.

The Deal That Was Almost Done

The Chicago Bulls were the front-runners. The proposed deal? A package involving Luol Deng, Ben Gordon, and a pile of draft picks. Kobe was reportedly on board — as long as Deng wasn’t part of the trade.

But the Lakers weren't willing to play ball without Deng being included. And just like that, the talks died.

What If It Had Happened?

Picture it: Kobe in a Bulls jersey. The legend, chasing championships in MJ’s shadow. That could’ve been magical or tragic (or both). Would Kobe have won without Pau Gasol? Would the Lakers have crumbled completely? Would Chicago have finally gotten over the post-Jordan hump?

Hard to say for sure. But one thing’s certain — the landscape of the late 2000s NBA would have looked very different.

MLB: Alex Rodriguez to the Red Sox

Yes, before A-Rod became a Yankee legend (and maybe a lightning rod for controversy), he was this close to joining Boston.

The Deal That Nearly Broke Baseball

In 2003, the Texas Rangers were tired of paying A-Rod's massive contract. The Red Sox were interested, and negotiations got really far. So far, in fact, that A-Rod even agreed to restructure his contract to help make the deal work under MLB’s financial rules.

But MLB’s Players Association wasn’t having it. They shot the deal down, saying it would set a bad precedent. The Red Sox couldn’t make the math work without that concession.

What If It Had Happened?

A-Rod batting alongside Manny Ramirez and David Ortiz? That lineup would’ve been every pitcher’s nightmare.

And what about the Yankees-Red Sox rivalry? Would A-Rod have helped Boston end the Curse of the Bambino sooner than 2004? Or would tensions have exploded if he ended up feuding with teammates like he later did in New York?

The butterfly effect here is massive.

NFL: The Time the 49ers Almost Got Peyton Manning

When Peyton Manning left the Indianapolis Colts in 2012, a bunch of teams lined up for a chance to sign him. The Denver Broncos eventually won that sweepstakes — but not without competition.

A Bold Plan in San Francisco

The San Francisco 49ers, who had just lost an overtime heartbreaker in the NFC Championship Game, were suitors. At that time, the team was stacked — a top-tier defense, a strong run game, and a hungry head coach in Jim Harbaugh. They were a quarterback away from a Super Bowl.

Manning met with the team and even went through some workouts. But in the end? He didn’t feel comfortable with the offense. He chose Denver.

The What-If Impact

Peyton Manning in a 49ers jersey, paired with that ferocious defense — you can practically see the Lombardi Trophies lining up.

Would Manning have led the Niners to multiple titles? Probably. Would Colin Kaepernick ever have seen the field? Probably not. That’s one quarterback decision that might’ve changed the course of several careers.

NHL: Wayne Gretzky to the Detroit Red Wings?

Let’s switch gears to the ice. Wayne Gretzky, "The Great One,” actually was traded from the Edmonton Oilers — that part we know. But what’s not widely talked about is that he could have landed in Detroit instead of Los Angeles.

The Behind-the-Scenes Drama

In 1988, the Oilers were shopping Gretzky due to financial pressure. Detroit was one of the top bidders, and they reportedly put together a better package than LA. But Gretzky's wife, actress Janet Jones, was drawn to Hollywood.

It’s said that Gretzky himself preferred Detroit, but the off-ice factors tipped the deal toward Los Angeles.

What If It Had Happened?

Gretzky in Detroit would’ve been wild. The Wings were on the cusp of greatness, and with him there? That dynasty might have kicked off years earlier.

Plus, the NHL's growth in the U.S. — especially in sunny California? Probably slower without Gretzky’s star power lighting up LA.

NBA: Chris Paul to the Lakers Vetoed by the League

You knew this one was coming. Possibly the most infamous blocked trade in modern sports history.

The Deal That (Literally) Got Shut Down

In 2011, the Lakers, Hornets, and Rockets agreed to a trade sending Chris Paul to Los Angeles. It was done. Locked in. CP3 was going to team up with Kobe Bryant and chase rings.

But then? NBA Commissioner David Stern, acting as owner of the league-controlled Hornets, vetoed the trade for “basketball reasons.” That was it. No Paul to LA.

What If It Had Happened?

Let’s be honest — this one hurts.

Chris Paul and Kobe Bryant running pick-and-rolls? That would’ve been electric. It could have extended Kobe’s prime, changed CP3’s legacy, and swung the entire balance of power in the West.

Instead, the Lakers struggled, Paul went to the Clippers, and we all got robbed of a dream pairing.

MLB: Bryce Harper to the Astros?

This one flew way under the radar, but it’s juicy.

The Little-Known Rumor

Back in 2018, the Washington Nationals were out of the playoff picture, and Bryce Harper was about to hit free agency. The Houston Astros — already a World Series favorite — wanted in.

According to some front-office insiders, a deal was agreed on, but Nats ownership pulled the plug at the last minute. They didn’t want to give up their franchise face for a couple of prospects.

What If It Had Happened?

Imagine Harper’s left-handed power in that stacked Houston lineup. It’s legit terrifying.

Would he have helped them win another World Series? Would he still have ended up in Philly? And how would fans have remembered his D.C. legacy if he’d been traded, even briefly?

It’s one of those ghost trades that brings more questions than answers.

NFL: The Saints Say No to Patrick Mahomes?

This one’s recent — and kind of painful for Saints fans.

The Almost Draft Night Deal

In 2017, the New Orleans Saints were sitting at the 11th pick. They had their eyes on a quarterback of the future. That quarterback? Patrick Mahomes.

But they didn’t move up. The Kansas City Chiefs did, jumping ahead of them to grab Mahomes at No. 10. The Saints took cornerback Marshon Lattimore instead — a solid pick, but still…

What If Mahomes Had Been a Saint?

Let that sink in. Patrick Mahomes as the heir to Drew Brees.

That dome would’ve turned into a Madden cheat code. Sean Payton calling plays for Mahomes? Forget about it — defenses would’ve just thrown up their hands in surrender.

Instead, Mahomes became a Chief and three trips to the Super Bowl later, well… the rest is history.

Final Thoughts: The Trades That Weren’t Still Matter

It’s wild how trades that never even happened still shape the way we view teams, players, and legacies. These near-misses have ripple effects — on championships, on contract decisions, even on fan loyalty.

They remind us that in sports, the margins are razor-thin. A blocked call, a vetoed trade, a draft pick not made — they all have the power to change everything.

And maybe that’s why we love it so much. Because in every “what if?” there’s a story as compelling as the truth.

So the next time your favorite team pulls out of a deal or misses on a player by one draft spot, just remember: history's biggest legends were often shaped by the trades that didn’t happen — not just the ones that did.