Vince McMahon is in the news for all the wrong reasons having announced his retirement, and these moments hurt his public image over the years.

Before Vince McMahon finally retired from WWE, he was like Teflon, enduring bad publicity that would sink most CEOs several times over. Surviving a steroid trial, the ring boy scandal, losing his temper on talk shows, and damning behavior on his own programming, McMahon navigated his way through a seemingly never-ending stream of negative press. It felt like all he had to do was double-down or outright lie, and sooner or later the problem would disappear.

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In theory, there was no one better to face a hostile media than McMahon, as he not only knew the company line, he was the company line. However, because he was rarely challenged inside the WWE bubble, when confronted by even a slightly antagonistic interviewer or reporter, McMahon was prone to tantrums that would make his company look like it was run by a bully.

The XFL's ratings were plummeting when Vince McMahon appeared on HBO with Bob Costas, so the WWE Chairman likely thought the appearance would help boost the public perception of his football start-up. Boy, that initiative couldn't have backfired more. McMahon came off as a meathead, who in lieu of a logical rebuttal to Costas' statements, opted for intimidation.

McMahon was especially short-tempered when, after claiming WWE had started to present less tawdry television content, Costas threw to a clip of an underwear-clad Trish Stratus on her hands and knees, groveling to McMahon, who was standing over her.

McMahon was no stranger to scripting himself to kiss beautiful women on his television. From 2001-2003 alone, he was involved in on-screen trysts with Trish Stratus, Torrie Wilson, Stacey Kiebler, and Sable.

YouTube videos of Vince swapping saliva with women he had power over, came back to haunt him. In June 2022, after reports of hush money payments came to light, it seemed like a case of life imitating art (or perhaps the other way around).

One night after announcing Brian Pillman's death at In Your House: Badd Blood 1997, WWE promoted an interview with Brian's widow, Melanie Pillman. It was placed in the Main Event segment and came off like a classless attempt to boost ratings against WCW Nitro.

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To make matters worse, McMahon kept asking probing questions that a distraught Mrs. Pillman was clearly not ready to answer.

A week after the Montreal Screwjob, McMahon had a sit-down interview with Jim Ross. It was an attempt at damage control in the wake of violating the trust of one of WWE's most loyal employees. The Chairman painted Bret Hart as a selfish malcontent who wouldn't adhere to the "time-honored tradition" of losing on the way out of the company, claiming "Bret screwed Bret".

McMahon's attempt to babyface himself was ineffective, as he came off as a sleazy heel to wrestling fans and the public. In the long-term, it actually worked in his favor as McMahon became a prolific super villain, doing record business as Steve Austin's foil.

McMahon should have known by 2003 to send a representative to speak on his behalf, as he was a one-man PR nightmare for his own company on a Real Sports episode on wrestler deaths.

After being questioned why so many of his employees were perishing before the age of 45, McMahon got defensive, saying he took no responsibility for the deaths. When interviewer Armen Keteyian pressed further, McMahon slapped Keteyian's notes out of his hands. Yet another example of McMahon being unable to control his temper.

Following the tragic death of Owen Hart at Over The Edge 1999, Vince McMahon held a press conference. It couldn't have been an easy experience for him to face the media after witnessing a long-standing employee plummet to his death, but that doesn't excuse the fact that he allowed the show to go on.

When questioned by a reporter, McMahon responded, "I don't like your tone, lady". This wasn't exactly a great display of poise and leadership.

This edition of LiveWire from the fall of 1996, presented Vince McMahon in all of his glory. He got to lay the HBK promotion on thick, saying that at Survivor Series, "Shawn Michaels proved that, not only was he a ladies man, as he has always been, but indeed Shawn Michaels is a man's man". He's like Uncle Leo talking about Jerry Seinfeld's cousin Jeffrey. Ever wonder why fans turned on HBK?

Vince also took live phone calls, where he displayed a thinly-veiled contempt for WWE fans. One particularly awkward call was from a host of a local wrestling radio show, telling McMahon that he wrote him a letter asking if he would come on the show as a guest. McMahon interrupted, saying he'd be "delighted" before the man revealed he received no response to his request. We all know that McMahon had no intention of ever going on that show.

In his WWE bubble, McMahon was an ultra-confident alpha male, and that came across when he appeared in a wrestling environment.

But whenever he ventured outside his domain on late-night talk shows like David Letterman or Conan O'Brien, McMahon came off as stiff and intimated by the standard of comedy set by the hosts.

In the midst of steroid and ring boy scandals, Vince McMahon appeared as part of a panel discussion on The Phil Donahue Show. Names like Bruno Sammartino, "Superstar" Billy Graham, Barry Orton, John Arezzi, and Dave Meltzer appeared on the show. Meltzer's presence was specifically requested by McMahon because he knew that the editor of the Wrestling Observer Newsletter would keep the facts straight for the audience watching at home.

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For the most part, it was everyone against McMahon, deserved or not. One particularly embarrassing moment for McMahon was when Arezzi asked if was true that he was devastated by the statements Hulk Hogan made about steroids on The Arsenio Hall Show. McMahon said, "I wasn't devastated", to which Meltzer immediately corrected, "Devastated is the word you used to me" followed by audience laughter.

WWE was rocked by a report of hush money payments McMahon made to an employee with whom he and John Laurinaitis had a sexual relationship. McMahon stepped down temporarily as CEO with Stephanie McMahon taking over for him on an interim basis, but Vince remained Head of Creative.

And instead of lying low until the investigation was complete, McMahon decided to appear on SmackDown, reminding fans of the mantra in WWE's opening signature, "Then. Now. Forever. And most importantly... Together", before doing a mic drop. It was a truly bizarre moment that felt extremely inappropriate. In July 2022, it was revealed other women were paid to keep quiet for a total of $12 Million. Weeks later, McMahon stepped down from all of his duties in the company, retiring from the WWE at the age of 77.

Colin Sharpe is a comedy writer, actor, and lifelong wrestling fan who cried when Bret Hart lost the belt to Bob Backlund. Follow him on Twitter @sharpethoughts