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I remember in the late 90's when Holly, who was almost exclusively a JTTS at the time and never really won matches, scored a random upset win over Owen Hart on Raw. They never really went anywhere with it or turned it into a push, so it didn't make a lot of sense and I pretty much forgot about it. Upon Owen's death Holly mentioned that it came about because Owen went to him and said "Hey we're in your home town, I want to put you over tonight," and upon request the match was made and it happened. Goes to show that Owen wasn't the huge mark for himself that so many wrestlers (his brother included) are.
I don't remember this particular story in the book (it may have been there and I'm forgetting) but Holly did have kind words to say about Owen and even said something to the effect of your last sentence.
Holly pointed out that some wrestlers - Like Bret - really thought they were a World Champion even though all it really meant was that Vince (in the case of WWF/E, obv.) was the one who decided you would be champion. You worded it better, the differences between a guy like Owen and Bret.
Holly was beyond loyal to the company but was only really interested in holding a title belt because it meant more money, especially on Pay-Per-Views, generally. As Holly pointed out, being a champ, or fighting for the champ, didn't always mean bigger payouts though. I was surprised - assuming he was telling the truth - at some of the paltry payouts he did receive the few times and did hold a mid-card title or had a world title match. He said for title match against Lesnar (I think it was?) he received like 1500 bucks. He said for walking to the ring once to interfere during a RAW he got like 5k. Seemed (maybe still is?) totally arbitrary.