Throughout his two stints in WWE, Jonathan Coachman was a jack-of-all-trades and ready to do whatever was called of him. Coach was a broadcaster, on-screen authority figure and even an occasional wrestler who was always great at taking bumps for Superstars.

His abilities endeared Coach to Vince McMahon who was the one who used him in a plethora of roles. Coach was asked about his relationship with Vince during an interview with Chris Van Vliet.

“For several years, I was very close. They had me doing everything. Back then, we did press conferences for every single pay-per-view. So, we would fly to the city before the pay-per-view to promote it. So, I was on his jet probably as much as anybody that wasn’t in full-time,” revealed Coach. “I would fly in his private jet all the time. People used to think it was great. It sucked because you cannot sleep unless Vince slept. That was the only time of the week where he would drink. He loves red wine.

“I think what endeared myself to him is that I proved I can do anything they need me to do, starting off as an announcer. He actually approached me and talked to me about becoming a character in 2003. To this day, there was never one time I ever said no to Vince. I said yes to everything.

“For Vince, he knew I was a good guy. He knew I came from a good family. He knew I was one of the normal people that got into wrestling. My dad is a retired minister. I used to bring him all the time and he kind of became a sounding board for guys like Shawn Michaels, Kurt Angle, even Vince. I would see my dad sitting in there at lunchtime, talking to Vince for a long period of time.

“I think all of that allowed me to endear myself to him, but also he trusted me. Trust is a big thing in that world because there are so many people that are untrustworthy. He knew that no matter how many people asked me to do it, I would do it. I would do it to the best of my abilities and I wouldn’t tell anybody.”

For all the talk that Vince McMahon gets from former employees for being ruthless, he also distills out advice to many young talents including wrestlers and commentators. Coach was asked what the biggest piece of advice he ever got from Vince was and he pointed to the tough love talk that Vince used to give him.

“I’m not going to use the word, but this is going to sound very crass. He used to always tell me, ‘Don’t be a *****’. It starts with a ‘P’. I believe people need to be tougher at certain times and in that world, it requires you to be tough all the time. Don’t take things personally, which is almost impossible to do, but also you got to believe in your talents and in yourself more than anybody,” said Coach.

“It’s such a subjective business. It’s not objective. It’s not cut and dry. If one person likes you, then your career can be amazing. If the wrong person doesn’t like you, you can be the most talented person in the world and not believe your talents will get you to where it should get you too. I think being tough was the one thing he taught me.”

You can tell that Coach and Vince had a great relationship because Vince went to great, great lengths to rib Coachman once. It even involved Coach being arrested, handcuffed and taking a ride in the back of a police car which Coachman remembers well.

“It was the beginning of the football season 2000-2001. We were in Fayetteville, North Carolina. Gerald Briscoe came up and said, ‘Hey Coach, you got to run a football pool for all the guys.’ Pay $10 and pick all of the games. I made photocopies and I’m just passing them out all day to everybody,” recalled Coach.

“My pre-tapes room was all the way at the end of the hall. In order for me to get out of the building, I had to walk by every single one of these rooms that had somebody in it. All of a sudden, I see two police officers, state troopers and they’re like, ‘Are you Mr. Coachman?’ I said, ‘Yes?’ They said, ‘Are you selling illegal football tickets?’ I said, ‘No.’ They showed me one of my photocopies. They said, ‘Just so you know, it’s a felony in North Carolina to run an illegal football pool. Unfortunately, we have to take you downtown.’

“My heart’s just going. I said, ‘Guys, come on, it’s a $10 football pool.’ They’re like, ‘Listen, the law was passed a few years ago. It doesn’t matter if it’s a dollar or a million dollars, it’s the same felony.’ I said, ‘Are you kidding me?’ They said, ‘No, we’re really sorry.’”

“We’re walking down and the cops are on either side of me and all of these people are looking at me. We get to Vince’s office and they’re like, ‘Does Vince run the whole show here?’ I said, ‘Yes’ and they said, ‘We really need to tell him.’”

As if being arrested at work wasn’t enough, Vince had to make things even more embarrassing for Coach by “helping” him by covering up Coach’s handcuffs with a certain object.

“They knock on the door and this is at three o’clock in the afternoon. The show starts in three hours and again, there were a lot of things that should’ve tipped me off, but I was terrified,” recalled Coach. “I walk in and there are five people in the room. Vince, Triple H, Stephanie, Gerald Briscoe, and Kevin Dunn.

“So, I walk into Vince’s office and he looks up. They said, ‘Excuse me, Mr. McMahon. Mr. Coachman is running an illegal football pool in the state of North Carolina. We just want to let you know that unfortunately, we have to arrest him.’ Vince walks over and his face is right here. So, I got his breath on my face. He goes, ‘A football pool? Do you not have anything else to do with your time all day than a football pool?’ I don’t say anything. I’m staring right at Gerald Briscoe, who’s the one who asked me to run it and he’s sitting there, saying nothing.

“The cops say, ‘Well, Mr. McMahon, it’s going to be like $1,500 to bail Mr. Coachman out of jail. Will you be helping him with that?’ He looks at me and goes, ‘F no, he’s on his own.’ ‘When somebody’s been arrested for a felony, they have to be handcuffed. So, we’re going to have to put handcuffs on him, and do you have like a towel or something at least so we can put it over his hands?’ Vince walks to his gym bag. He picks up the boxer shorts he wore to work out on that day. Whips them at me and it sticks to my face.

“Everybody in there is dead silent. It was so awkward. We walk out and the first person we see was The Undertaker. I’ve never felt more shame in my life.

“They put the seatbelt on me because I’m in handcuffs and I’m thinking how do I tell my father that my career could be over because I have a felony for running a $10 football pool. Our head of the security at the time, Jimmy Tillis, goes, ‘Coach, say nothing. I’ll come down and bail you out.’ They take me around and drive two or three miles. On their radio, they say, ‘Mr. Tillis can’t get his car out. Can you pick him up?’ The cop’s like, ‘Hey man, this is a little unorthodox, but if you want somebody to give you a ride home, we got to go pick them up.’ We drive back and all they were doing was killing time to get everybody to come out of the arena. We come down a big hill and everybody’s standing out there. I still don’t know what’s happening.”

When Coach saw the entire locker room and all of the WWE employees waiting for him, he finally realized he had just been ribbed. But he was sweating bullets the whole time and couldn’t even take the joke in stride because he was so nervous that he was going to get fired.

“They opened the door and it took 45 minutes to pull this off from start to finish, which is why they call it the greatest rib because it went longer than they could’ve imagined,” stated Coach. “We get out and everybody’s like, ‘Oh man, you’re amazing!’ I’m still in handcuffs. I was like, ‘Somebody gets these handcuffs off of me.’ Everybody’s patting me on the back.

“I literally went to the part of the arena where nobody could find me and I just started sobbing. I was crying so hard. I was just so relieved that I wasn’t going to jail, that I wasn’t arrested and that I still had a job. It took 45 minutes and to this day, he still calls it the greatest rib.”

If you use any of the quotes in this article, please credit Insight with Chris Van Vliet with a h/t to Wrestling Inc. for the transcription.