More than two decades after one of the most memorable matches in WWE history, Jim Ross has reflected on the iconic Undisputed Championship Ladder Match between The Undertaker and Jeff Hardy, revealing just how much the WWE Hall of Famer sacrificed to help elevate Hardy into a singles star.

Looking back on the July 1, 2002 edition of Raw from Manchester, New Hampshire, Ross explained in an excerpt from his book, shared on Grilling JR, that The Undertaker stepped far outside his comfort zone because he believed it was the best way to establish Hardy as a credible main event talent.

Ross began by emphasizing that growth in wrestling comes from embracing uncomfortable situations.

“If you get stuck in your comfort zone, you begin to die. It’s true of life. It’s also true of wrestling,” Ross said. “The best talents are always pushing themselves out of their comfort zone to stay as far ahead of the game as they possibly can for as long as they can.”

At the time, WWE had split The Hardy Boyz and was exploring whether Jeff Hardy could succeed as a solo performer. According to Ross, The Undertaker played a crucial role in making that transition happen.

“WWE was interested in seeing if Jeff could become a star in the singles division, but had no idea how to get him there. So up stepped The Undertaker,” Ross said. “I don’t know how many six foot ten, 300 pound men like to climb, wrestle on, or fall off a 16 foot ladder, but Undertaker was not one of those men. He hated doing this match so much that it was his only ladder match in a 35 year career, but he knew it was the optimal setting to highlight Jeff’s more flashy daredevil style. So a ladder match it was.”

Ross also praised the structure of the match, saying it became obvious to him that The Undertaker had been heavily involved in putting it together.

“I like to know as little as possible before a show, so my reactions out there are real and unrehearsed. But when the bell rang, I could tell immediately that Undertaker had a hand in laying out the match itself,” Ross said. “I could tell he was involved mostly because of the story they were telling. It was deliberate building and pacing in a way that made the audience wait as long as possible without ever losing them before hitting the higher gears.”

For Ross, the contest perfectly illustrated wrestling's ability to elevate both competitors, even when only one leaves with the victory.

“In pro wrestling, there’s usually a winner and a loser, but when you control the outcome for both guys, you can have the loser leave more elevated in the fans’ eyes than when he walked in,” Ross said. “One takes the victory, and one takes victory in defeat. Or one goes over, one gets over. It’s hard as hell to pull off unless you’re an egoless veteran who can pull all the levers that are necessary in a skillful and timely manner.”

Ross admitted he became completely invested in the action as it unfolded.

“Through hellacious bumps and stiff chair shots, Hardy and Taker made the audience believe. They made me believe too,” Ross said. “I felt every second of that match, the passion of it, the will to win.”

The defining moment came after the match ended. Hardy, despite losing, challenged The Undertaker's respect by insisting he was not finished. Rather than striking him, The Undertaker acknowledged his effort by raising Hardy's hand.

“With that little piece of business, the story was told,” Ross said. “The challenger, now broken out of his tag team only mode, was suddenly seen as a main event player.”

Ross noted that Hardy would later capture six world championships across multiple promotions, while crediting The Undertaker's selfless approach as a major reason the match became so influential.

“This is why Mark had such an amazing career with just one character in WWE. He was able to adjust and overcome all the fads, changes and eras to keep his work fresh, varied and always at the top of the card,” Ross said. “In my view, he’s WWE’s greatest character ever.”

Reflecting on the contest years later, Ross still ranks it among his favourite memories behind the commentary desk.

“That’s a great match. That was a great match, man,” he said. “It’s a really exciting day at work. Those are the days that you want to replicate. It was one of my finer moments, between two guys that I had a lot of appreciation and respect for.”