While reflecting on his tenure as WWE’s head of talent relations, Jim Ross was asked to identify the least successful signing he was involved with during that period — and his answer was candid.
Speaking on his podcast, Ross pointed to Tiger Ali Singh, the son of Tiger Jeet Singh, as a talent the company ultimately invested significant time in without seeing the desired return.
“I think maybe the one that we wasted a lot of time on was Tiger Jeet Singh’s son. Tiger Ali Singh.
Nice kid. Good-looking. Smart. He just didn’t have the natural ability to connect to the audience. He looked good. He looked the part. Vince [McMahon] loved him, and what Vince was looking at was opening up international markets, where Tiger Ali Singh would have been a viable option.”
Ross went on to share an anecdote that highlighted early warning signs during Singh’s run, specifically regarding expectations and presentation. According to Ross, Singh made an unusual demand during contract discussions.
“But it was funny. When I signed him, he wanted—he almost demanded—to fly first class. I kicked that idea back because that’s not what Vince wanted to do, and Vince would have squashed it anyway.”
A compromise was eventually reached, one designed more for perception than reality.
“So we had a compromise. He would fly first class on the last leg of his tour. When he got off the plane in Toronto—where he lived, where he’s from—he would be with that group of first-class passengers that got off the plane first, so people could see him get off first and assume automatically that he was riding first class like a star.”
Despite those efforts, Ross admitted the experiment ultimately failed to deliver results in the ring or with audiences.
“So we did that for him, and it still didn’t work out. But I wish it would have worked, because he could have made a fortune in international markets without question.”
Ross’ comments offer a rare behind-the-scenes look at WWE’s talent evaluation process during that era — and how marketability, presentation, and in-ring connection don’t always align, even when all the right pieces appear to be in place.
