Episode 370: Tough Business

Grilling JR1h 4mMay 7, 2026

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AI-Generated Summary

In Episode 370 of *Grilling JR*, host Conrad Brown and WWE Hall of Famer Jim Ross dive into a wide-ranging conversation covering recent developments in professional wrestling, including WWE’s controversial decision to offer 50% pay cuts to several top performers—such as Kofi Kingston and Xavier Woods—despite their five-year contracts expiring in 2030. Ross breaks down the business reality behind such moves, emphasizing that contracts often include escape clauses and that talent should negotiate for guaranteed terms. He reflects on his own career in WCW and WWE, sharing candid insights about talent management, creative decisions, and the emotional toll of difficult cuts. The episode also explores the cultural evolution of wrestling, from unique venues like the proposed Alcatraz match to the controversial use of gimmick matches and celebrity crossovers. Ross expresses skepticism toward over-the-top stunts and music integrations, favoring authenticity and storytelling. The episode closes with a powerful, emotionally charged retrospective on the legendary WrestleMania 25 match between Shawn Michaels and The Undertaker, which Ross calls a masterpiece of artistry and human resilience.

Key Takeaways
1

Contracts in wrestling are rarely fully guaranteed—talent should negotiate for 5-year guarantees to avoid sudden pay cuts.

2

WWE’s recent cuts may signal deeper financial restructuring, not just talent issues, and could be part of a broader corporate efficiency push.

3

Unique venues like golf arenas or Alcatraz could enhance storytelling, but authenticity and performance should remain the priority over spectacle.

4

The Shawn Michaels vs. Undertaker match at WrestleMania 25 remains one of the greatest wrestling matches ever due to emotional depth, storytelling, and mutual respect.

5

Talent should use downtime to improve their craft—step away, train, and build value before re-entering the market.

…and 3 more takeaways available in PodZeus

Chapters
0:00
10 min

WWE's Record Profits and Sudden Pay Cuts

You don’t get five guaranteed years just because you signed a five-year deal. If you don’t negotiate that in, you’re stupid.

Highlight
10:00
10 min

The Art of the Wrestling Match: Michaels vs. Undertaker

I had goosebumps. I had tears in my eyes. I was so emotionally wrapped up in that presentation.

Highlight
20:00
10 min

Venue Innovation and the Future of Wrestling Events

The hosts discuss AEW’s upcoming 'Fairway to Hell' event, set in a golf arena, and Ross shares his long-held idea of holding a match at Alcatraz. He reflects on past unique venues like the floating ring in Panama City Beach and the Sturgis Rally, weighing the pros and cons of spectacle versus substance.

30:00
10 min

Talent Management and the Reality of the Business

Ross shares personal anecdotes from his time in WCW and WWE, discussing how he managed talent, handled creative disagreements, and made tough decisions. He emphasizes loyalty, performance, and the importance of not overpricing talent, even during peak success.

40:00
10 min

The Decline of House Shows and the New Training Model

The conversation turns to WWE’s elimination of house shows, with Drew McIntyre citing injury concerns and the need for more individualized training. Ross weighs in on the trade-offs between developmental opportunities and personal life, acknowledging the emotional toll of constant travel.

High-Impact Quotes
I had goosebumps. I had tears in my eyes. I was so emotionally wrapped up in that presentation.
Jim Ross64:08
Viral: 90.0
This was the mood nobody gets up front. The Undertaker sold the shit out of Michael's kicking out of everything he had.
Jim Ross61:26
Viral: 88.0
You don’t get five guaranteed years just because you signed a five-year deal. If you don’t negotiate that in, you’re stupid.
Jim Ross32:25
Viral: 85.0
Speakers

Host

Conrad Brown

Guest

Jim Ross
Topics Discussed
WWE Contract Negotiations95%Wrestling Match Artistry92%Talent Management and Career Longevity88%Business Realities in Professional Wrestling87%Venue Innovation in Wrestling85%Wrestling Storytelling and Character Development83%The Decline of House Shows80%Celebrity Crossovers in Wrestling70%
People & Brands

Jim Ross

person

120xPositive

Conrad Brown

person

85xPositive

WWE

organization

45xMixed

The Undertaker

person

40xPositive

Shawn Michaels

person

35xPositive

AEW

organization

30xPositive

Kofi Kingston

person

25xPositive

WrestleMania 25

other

25xPositive

Xavier Woods

person

20xPositive

Finn Bálor

person

15xPositive

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