There are two very different sides to the Tim Witherspoon story.

The gifted boxer-puncher from South Philadelphia became only the third man in boxing history to regain a heavyweight title (Floyd Patterson and Muhammad Ali preceded him), accomplishing that feat in the mid-1980s. This statistic alone should be enough to turn heads, but Witherspoon’s overall resume and craft are very underrated.

With virtually no amateur career to speak of and only 15 professional fights, Witherspoon pushed a prime Larry Holmes (42-0) to the limit in May 1983, and the split decision defeat – his first setback – could easily have gone the other way. He fought brilliantly that night, hurting the great champion badly in what was later named The Ring Magazine Round of the Year (9). Witherspoon bounced back quickly, and over the next three years claimed wins over James Tillis, Greg Page (won vacant WBC title), James “Bonecrusher” Smith, Tony Tubbs (won WBA title) and Frank Bruno.

But while his success inside the ring was undeniable, there were big problems outside of it, and the resulting negativity unfairly plagues Witherspoon’s impact. Constant financial battles with promoter Don King led to a lack of motivation, inconsistent form and disappointing results. He would overcome a close decision loss to Pinklon Thomas in August 1984, but a rematch with the aforementioned Smith ended in a first-round defeat and sent Witherspoon’s career into a tailspin in late ’86. The two-time titleholder insists that he was so disenchanted with the business side of the sport that he actually “threw” the Smith rematch, but while his career continued, the glory days were over.

“I was just putting money on the table and taking care of the kids. I won some fights, but I was really just trying to stay afloat.” acknowledged Witherspoon, who successfully sued King in 1992, settling out of court for a reported $1 million.

“Eventually I retired because you can get hurt playing around, trying to make money in boxing when you’re getting older. I learned a lesson, but I wouldn’t change anything. People know what happened to me (with Don King). They know I fought against it and that’s pretty cool. I would do the same thing all over again.”

“Terrible” Tim Witherspoon (55-13-1, 38 knockouts) took on a horde of terrific fighters in the 80s and 90s and now looks back on some of his defining moments:

Witherspoon (right) pressures Larry Holmes. Photo from The Ring archive/ Getty Images

Larry Holmes
Date Venue: May 20, 1983/ Dunes Hotel & Casino, Las Vegas
Titles: Ring Magazine/ WBC heavyweight

“What made me confident [of winning the fight] was my trainer. At first, I doubted that I could win when Don King told us to take the fight. Actually, the first thing I said to my trainer was, ‘Slim [Jim Robinson], don’t you think it’s a little too soon?’ He said, ‘Tim, we’re gonna kick his ass!’ That’s what gave me the confidence, and we started training really hard. I was friends with [Michael] Dokes, [Leon] Spinks, David Bey, Mitch Green, Azumah Nelson … we were all in the same camp together. Everyone was happy for me when I was training for the Larry Holmes fight. But I was also really confident because of where I came from. I’m from 7th Street in South Philly, down near the Italian market where Sylvester Stallone shot his movie, Rocky. I’m the real two-time heavyweight champ from Philly. I wasn’t going to let Larry Holmes scare me because he had more experience. I wasn’t going to let him get the best of me and he didn’t.”

Result: Holmes SD 12

James Tillis
Date/ Venue: September 23, 1983/ Richfield Coliseum, Richfield
Titles: Non-title bout

“I was going to fight ‘Quick’ Tillis the year before, but I got my jaw broken. I was messing around in sparring with a light heavyweight named “Lightning” Bob Smith. I was showing him how to throw a left hook, and when I was talking to him, he threw a left hook and broke my jaw. That put me out for a whole year. Later on, I’m in an elevator with Tillis and he says that I’m scared to fight him and that I’m a punk. I said ‘OK, wait until next time!’ I trained real hard, I was chopping wood, and I was boxing real well. I anticipated some good boxing from him, but he’d said things that made me angry and aggressive. That’s why I approached him the way I did. There was a three-knockdown rule, I knocked him down three times, and I hurt him. I used leverage, delivered the punches properly and they landed right on the chin. He was a good fighter and went 10 rounds with [Mike] Tyson after that.”

Result: Witherspoon TKO 1

Witherspoon (left) picks up his first title belt at the expense of Greg Page. Photo from The Ring archive/ Getty Images

Greg Page
Date/ Venue: March 9, 1984/ Convention Center, Las Vegas
Titles: Vacant WBC heavyweight

“I was excited about the fight, but both of us had the same problem and that was the promoter (Don King). How can we train for a heavyweight championship fight when things aren’t in order? It was the financials. Most Don King fighters would have disagreements about money and very few didn’t. I wanted the title, so I just kept pushing and got the victory, but I wasn’t really happy with that particular fight. We both had mental problems because of the contract negotiations, and we were both angry. [Page] was supposed to be the next guy to get the title, but even though I came out on top, I couldn’t enjoy the win, because the person who was running the show was taking the money. It was a shame for the fighters back then because I think we were some of America’s best up-and-coming heavyweights. The money was there before us, after us, but not for us.”

Result: Witherspoon MD 12

Tony Tubbs
Date/ Venue: January 17, 1986/ The Omni, Atlanta
Titles: WBA heavyweight

“He was a very intelligent boxer, very elusive. I think if he had the right training and the right people behind him, he would have produced a lot more [in his career.] Tubbs was a guy that made you think, made you move, because he was slick. You can’t hit him, but he’s already jabbed at you and scored. In good shape, he was a really good boxer, but I put the pressure on him because I knew he was upset with the business side of things and Don. I still had trouble with Don, but we both had to fight. Tony Tubbs threw a lot of punches, but he didn’t hit hard enough to knock me out. I was prepared, but my mind was still in another world. Again, I won the title, but I didn’t get the ice cream and cake that goes with it. I didn’t get the caviar. I didn’t get the money. I only got paid 50 grand for that fight, then the IRS came, took all the money, and I had to borrow $10,000 from Don.”

Result: Witherspoon MD 15

Witherspoon emptied Frank Bruno’s tank before lowering the boom. Photo by S&G/ PA Images via Getty Images

Frank Bruno
Date/ Venue: July 19, 1986/ Wembley Stadium, London
Titles: WBA heavyweight

“I didn’t know how big the fight was until we got over there. I always wanted to go into someone else’s backyard and defend my title, so this was a dream come true for me. I was being treated like a big-time celebrity in another country; big crowds at the airport, going around in limos. This was actually the first time I really felt something; the first time I really felt like, ‘Oh, I am the champ!’ I was prepared for the fight, but it was almost like a vacation, so I relaxed, slowed down and put on a couple of pounds. I’d been gung-ho in training [in the U.S.], but when I came over there, I started eating a bit more. They were even sending women to me and that’s when my trainer said, ‘Hell no!’ They had us training in London, but we moved out to Basildon (in Essex) and we were sleeping above a pub (laughs). That was a great win in my career, and I was respected for it over there. I had a good manner, so people were really kind to me.”

Result: Witherspoon TKO 11

Jorge Luis Gonzalez
Date/ Venue: May 10, 1996/ Madison Square Garden, New York
Titles: Non-title

“A lot of people didn’t like him and that gave me energy. He had an arrogant attitude, but when I went to his dressing room after knocking him out, he was really cool. Before the fight, people were coming up to me and saying, ‘Knock him out, man! I don’t like his attitude!’ Several people were telling me to knock his ass out, so that gave me energy too. If you look at the video, the [left] uppercut started it. We locked arms and when I broke loose, I landed the uppercut. After that fight, there were rumors that [Mike] Tyson’s, [Evander] Holyfield’s and [Lennox] Lewis’ management were avoiding me. I don’t think the fighters avoided me, they would fight me tomorrow, but their management was scared because they never knew what Tim Witherspoon was going to show up.”

Result: Witherspoon TKO 5

YOU MAY HAVE MISSED

LARRY HOLMES: THE GREATEST HITS

Tom Gray is Associate Editor for Ring Magazine. Follow him on Twitter: @Tom_Gray_Boxing

READ THE LATEST ISSUE OF THE RING FOR FREE VIA THE NEW APP NOW. SUBSCRIBE NOW TO ACCESS MORE THAN 10 YEARS OF BACK ISSUES.