5 Times the Monday Night Wars Almost Went Completely Differently

The Undertaker nearly bolting to WCW is just the latest reminder of how a few decisions reshaped wrestling history — here are the near-misses that matter most.

The Undertaker recently opened up on his Six Feet Under podcast about how close he came to jumping to WCW during the darkest stretch of the Monday Night Wars, and it got us thinking. The Wars weren’t won by one big moment — they were decided by a thousand tiny forks in the road. So we’re ranking the near-misses, the almost-decisions, and the loyalty tests that could have flipped the entire war. Here’s our list, ordered by how badly each one would have changed everything.

5. AEW Nearly Ejecting Jacques Rougeau — A Modern Echo of Old Grudges

Okay, this one’s a wildcard, but bear with us. The report that AEW nearly ejected Jacques Rougeau over a tribute video dispute at Redemption is a reminder that the personality clashes and ego wars that defined the WCW-era backstage never really went away. The Mountie was a product of that chaotic territory-to-national transition. Watching a legend from that world create a modern-day headache is proof the culture of the Wars still lingers in every locker room. Low on the list because it’s a footnote, but it’s a telling one.

4. Kurt Angle Signing With WWE Instead of Anyone Else

Thirty years ago, Kurt Angle won Olympic gold with a broken freakin’ neck. When he transitioned to pro wrestling, WWE landed him — and imagine if WCW had gotten there first. Angle was the most legitimate athlete either company could have paraded around. In a war built on credibility and star-making, a real Olympic hero was a rocket the moment he laced boots. WWE turning him into a top guy almost overnight is one of the great talent-development wins of the era. Had he landed in Atlanta’s bloated roster, he might have rotted in the midcard like a dozen other future legends did.

3. WCW Losing the Battle for Loyalty It Should Have Won

Here’s the thing WCW never understood: money isn’t everything. The company was famous for backing up Brinks trucks to poach WWE stars, and it worked — until it didn’t. The reason it eventually didn’t work is people like The Undertaker, who valued being built into something over being paid to disappear into a crowded main event scene. WCW’s inability to convert its financial advantage into genuine loyalty is arguably why it collapsed despite outspending its rival for years. This ranks high because it’s the meta-lesson of the entire war.

2. The Undertaker Staying Loyal to WWE

Straight to the source: The Undertaker recently explained why he turned down WCW during the period when WWE looked like it might genuinely lose. Think about what The Deadman represented — a character so tied to WWE’s identity that it’s almost impossible to picture him under the WCW banner. If he leaves during the Nitro-dominated stretch, WWE loses one of its few remaining anchors at exactly the moment it could least afford to. His loyalty wasn’t just a personal choice; it was a load-bearing pillar of the company surviving long enough to launch the Attitude Era. This is the near-miss that mattered most on a human level.

1. The Attitude Era Talent WWE Managed to Keep and Develop

At the top of the list: the collective decision-making that let WWE hold and elevate the right people while WCW squandered its head start. The war wasn’t lost in one night — it was lost because one company kept building new stars while the other kept recycling old ones. That philosophy still defines the industry. You can draw a straight line from those choices to how WWE and its rivals develop talent today, whether it’s rocket-pushing a prospect on a mega-show or the way AEW is quietly building an entire ecosystem with its expanding MyAEW streaming platform. The lesson of the Monday Night Wars is eternal: you win by making stars, not renting them.

The Takeaway

The Wars feel like ancient history now, but every one of these near-misses shaped the promotions we watch today. One Undertaker signing here, one Angle contract there, and the whole map redraws itself. That’s what makes this era endlessly re-litigable — the margins were razor-thin.

Which near-miss do you think would have changed history the most? Drop your picks in the comments and let’s argue about it.