Evander Holyfield: undisputed at cruiserweight, then the first four time heavyweight champion | Ultimate Boxing Reunion

The painting

Hang this painting and someone will always point at a face and ask, “Who’s that?” Dean Turner’s Ultimate Boxing Reunion is a hand-painted original of 39 boxing greats, painted over six months. This is the story of one of them, Evander Holyfield. It’s available as a framed canvas print, made from the original, for your favourite place.

No. 31 Who’s Who Ultimate Boxing Reunion

undisputed at cruiserweight, then the first four time heavyweight champion

He started boxing at eight in a boys club in Atlanta, and in 1988 he became the first undisputed cruiserweight champion. He moved up, knocked out Buster Douglas in 1990 to become undisputed heavyweight champion, and in 1996 he stopped Mike Tyson, Who’s Who number 34 as a 25 to 1 opening underdog. In 2000 he became the first man to win a heavyweight title four times.

Evander Holyfield as painted by Dean Turner Art in Ultimate Boxing Reunion 31of 39
On the Who’s Who Evander Holyfield Number 31 of 39 in Ultimate Boxing Reunion. A detail of Evander Holyfield, with the full scene. See who’s who in the painting
In this story 14 sections

Why fans still care

EVANDER HOLYFIELD won every cruiserweight belt there was, then moved up and won the heavyweight title four times, the first man to do it. He beat George Foreman, Who’s Who number 35 and Larry Holmes, Who’s Who number 19, fought Riddick Bowe three times and Lennox Lewis, Who’s Who number 29 twice.

Most of all, people remember the night in 1996 when he stopped Mike Tyson, Who’s Who number 34. ESPN’s Dan Rafael wrote that he “bullied the bully”.

Early life

He was born in Atmore, Alabama, on 19 October 1962. His mother, Annie, taught him to work hardest and take no shortcuts. The family moved to Atlanta when he was five, and three years later, according to the New Georgia Encyclopedia, he started boxing at the Warren Memorial Boys Club in south east Atlanta.

The New Georgia Encyclopedia records that at 11 he qualified for the Junior Olympics, and at 16 he won the south eastern regional title and the best boxer award. Watching Leon Spinks, Who’s Who number 30 and his brother Michael on television made him believe he could make the Olympic team. “No one in my neighborhood could tell me I couldn’t make the Olympic team,” he told Sports Illustrated in 2011.

The early fights

At the 1983 Pan American Games in Caracas he won silver, the New Georgia Encyclopedia notes. At the 1984 Olympics in Los Angeles he boxed at light heavyweight. In the semi-final he floored New Zealand’s Kevin Barry, but the referee, Gligorije Novičić of Yugoslavia, disqualified Holyfield for fighting on after the call of “break”. Barry could not box in the final and took silver. Holyfield took bronze.

He turned professional on 15 November 1984 against Lionel Byarm in New York.

Career chapters

  1. 1984Olympic bronze in Los Angeles, then his professional debut on 15 November
  2. 1986Wins the WBA cruiserweight title from Dwight Muhammad Qawi in his 12th fight
  3. 1987Stops Rickey Parkey to add the IBF title
  4. 1988Stops Carlos De León to become the first undisputed cruiserweight champion, then moves up
  5. 1990Knocks out Buster Douglas to become undisputed heavyweight champion
  6. 1991Beats George Foreman, Who’s Who number 35 on points
  7. 1992Beats Larry Holmes, Who’s Who number 19, then loses the titles to Riddick Bowe
  8. 1993Regains the WBA and IBF titles from Bowe
  9. 1994Loses the titles to Michael Moorer
  10. 1996Stops Mike Tyson, Who’s Who number 34 in round 11
  11. 1997Wins the rematch by disqualification, then stops Moorer to add the IBF title
  12. 1999Draws with and then loses to Lennox Lewis, Who’s Who number 29
  13. 2000Beats John Ruiz to become the first four time heavyweight champion
  14. 2011Stops Brian Nielsen in Copenhagen in his last professional fight
  15. 2017Inducted into the International Boxing Hall of Fame

Dwight Muhammad Qawi 12 July 1986

On 12 July 1986 at the Omni Coliseum in Atlanta he won the WBA cruiserweight title from Dwight Muhammad Qawi over 15 rounds, on a split decision. Two judges scored it 144 to 140 and 147 to 138 for Holyfield, and the third had it 143 to 141 for Qawi. It was only his 12th professional fight. Years later he told ESPN, “Qawi was by far the toughest fight.”

Undisputed at cruiserweight 1987 and 1988

On 15 May 1987 at Caesars Palace he stopped Rickey Parkey at 2:44 of round 3 to add the IBF title. On 9 April 1988, also at Caesars Palace, he stopped Carlos De León at 1:08 of round 8, with Mills Lane the referee, to take the WBC belt. That made him the first undisputed cruiserweight champion. In July 1988 he gave up the cruiserweight titles to move up to heavyweight.

Buster Douglas 25 October 1990

On 25 October 1990 at The Mirage in Las Vegas he fought James “Buster” Douglas for the WBA, WBC and IBF heavyweight titles. At the weigh in Douglas was 246 pounds and Holyfield 208. Holyfield knocked him out in round 3 and became the undisputed heavyweight champion.

Foreman and Holmes 1991 and 1992

On 19 April 1991 at Convention Hall in Atlantic City he beat George Foreman, Who’s Who number 35 on a unanimous decision over 12 rounds. On 19 June 1992 at Caesars Palace he beat Larry Holmes, Who’s Who number 19, also on a unanimous decision over 12 rounds.

Riddick Bowe, the first fight 13 November 1992

On 13 November 1992 at the Thomas & Mack Center he lost the titles to Riddick Bowe on a unanimous decision. Bowe cut him over the left eye in round 8. In round 10 both men landed heavy blows and fought on after the bell until the referee, Joe Cortez, separated them, and the LA Times called it one of the great rounds in heavyweight history. In round 11 Bowe put him down, the only knockdown, and he rose to take an eight count from Cortez. The cards were 117 to 110 twice and 115 to 112. Afterwards, in the interview room, Bowe embraced him.

Riddick Bowe, the second fight 6 November 1993

On 6 November 1993 at Caesars Palace he won the WBA and IBF titles back from Bowe on a majority decision, 115 to 113, 114 to 114 and 115 to 114. Emanuel Steward trained him for it. About a minute into round 7 a parasailer, James Miller, crash landed at ringside, and the fight was held up for 22 minutes in front of 14,242 people. It is remembered as the “Fan Man” fight. Holyfield became the third man to regain the heavyweight title, after Floyd Patterson and Muhammad Ali, Who’s Who number 33.

Moorer and the third Bowe fight 1994 and 1995

On 22 April 1994 he lost the titles to Michael Moorer on a majority decision. He boxed on, and on 4 November 1995 Bowe stopped him in round 8 in a fight with no title at stake. Bowe won their series two fights to one.

Mike Tyson, the first fight 9 November 1996

On 9 November 1996 at the MGM Grand Garden Arena he fought Mike Tyson, Who’s Who number 34 for the WBA title. He opened as a 25 to 1 underdog, and the odds closed at 15 to 2, as Sports Illustrated recalled in 2012. Don Turner, his trainer with Tommy Brooks, told him to counter at once whenever Tyson landed. Holyfield put Tyson down in round 6. The referee, Mitch Halpern, stopped it 37 seconds into round 11.

He later said he answered Tyson’s rough work in kind and did not complain to the referee, and that in round 11 he jabbed to make Tyson reach so he could land the right hand.

Mike Tyson, the second fight 28 June 1997

On 28 June 1997 they met again at the MGM Grand. In round 3 Tyson bit Holyfield’s right ear and then his left. The referee, Mills Lane, took two points from Tyson and then disqualified him. Nevada revoked Tyson’s licence on 9 July 1997 and fined him $2.98 million. Promoter Don King, Who’s Who number 18 later said of Holyfield, “He was fearless.”

Moorer and Lewis 1997 to 1999

On 8 November 1997 at the Thomas & Mack Center he knocked Moorer down five times, and the ringside doctor, Flip Homansky, stopped it after round 8. It added the IBF belt. On 13 March 1999 at Madison Square Garden he fought Lennox Lewis, Who’s Who number 29 in front of 21,284 people. It was a split draw, 115 to 115, 116 to 113 for Lewis and 115 to 113 for Holyfield, and his purse was $20 million. The draw was disputed, and Holyfield said the people around the ring “are not the judges”. On 13 November 1999 at the Thomas & Mack Center in Las Vegas Lewis won the rematch on a unanimous decision, 117 to 111, 116 to 112 and 115 to 113. “I’m not embarrassed by my performance,” Holyfield said.

John Ruiz and the later fights 2000 onwards

On 12 August 2000 at Paris Las Vegas he beat John Ruiz on a unanimous decision over 12 rounds for the vacant WBA title. It made him the first man to win the heavyweight title four times. Ruiz beat him on 3 March 2001, and their third fight on 15 December 2001 was a draw. He beat Hasim Rahman on a technical decision in 2002 and boxed on until 7 May 2011, when he stopped Brian Nielsen in round 10 in Copenhagen in his last professional fight.

Style, technique and the corner

How he fought

He was a pressure fighter who would match rough tactics. Against Tyson in 1996, by his own account, he answered the arm twisting and elbows in kind. He also tried to land the last punch of every round, because it is the one people remember.

The name

He was known as “The Real Deal”, and he wore “Warrior” on his trunks.

Training

He learned the game at the Warren Memorial Boys Club in Atlanta from about the age of eight. Emanuel Steward trained him for the second Bowe fight in 1993. Don Turner, with Tommy Brooks, trained him for both Tyson wins.

The corner

For the first Tyson fight, Turner’s plan was simple: counter at once whenever Tyson landed. It was his last instruction before the bell.

What others say

“Holyfield was the best opponent I faced in my career.”

Lennox Lewis, Who’s Who number 29, who fought him twice in 1999 (second-hand: from an interview with The Ring, as reported by Boxing News and Seconds Out)Source: Boxing News (Shaun Brown), 30 Nov 2025. https://boxingnewsonline.net/news/lennox-lewis-names-best-he-faced ; Seconds Out, 6 Sep 2025

“Holyfield took the shot and hit him right back.”

Teddy Atlas, trainer and ESPN commentator, on the Tyson fightsSource: Sports Illustrated (Gabriel Baumgaertner), 29 Jun 2012

“He was fearless. It was an amazing thing.”

Don King, Who’s Who number 18, promoter of both Tyson fightsSource: Sports Illustrated (Gabriel Baumgaertner), 29 Jun 2012

“He uses everything he has, and against Mike Tyson, I probably would too.”

Bobby Czyz, former champion who fought him in 1996, on his rough tacticsSource: Sports Illustrated (Gabriel Baumgaertner), 29 Jun 2012

“You’ve got nothing to be ashamed about.”

Riddick Bowe, who beat him in 1992, in the interview room after the fightSource: Los Angeles Times (Earl Gustkey), 14 Nov 1992

“Great champion: chin, heart, determination, work ethic, demeanor.”

Mike Tyson, Who’s Who number 34, who fought him twice, naming him the best he faced (second-hand: from a feature with The Ring, as reported by Seconds Out)Source: Seconds Out (Kailem Lowe), 5 Dec 2025

“Evander was smart, he was a thinker, he was in great shape, he had all the attributes to make him a great champion.”

Riddick Bowe, who fought him three times, naming him the best he faced (second-hand: from a feature with The Ring, as reported by Seconds Out)Source: Seconds Out (Kailem Lowe), 5 Dec 2025

“I was like many journalists who thought he would never be the heavyweight champion of the world. He proved everyone wrong and did it four times.”

Steve Farhood, boxing journalist and Showtime commentator, inducted into the Hall of Fame alongside him in 2017Source: Las Vegas Review-Journal (Gilbert Manzano), 9 Jun 2017

Stories people still tell

  1. The Fan Man.

    In the second Bowe fight in 1993, a parasailer crash landed at ringside in round 7. The fight was held up for 22 minutes, and Holyfield went on to win the titles back.

  2. The 1984 semi-final.

    He floored Kevin Barry in the Olympic semi-final, and the referee disqualified him for fighting on after “break”. Barry could not box in the final and took silver, and Holyfield went home with bronze.

  3. Giving away weight.

    Against Buster Douglas in 1990 he weighed 208 pounds to Douglas’s 246, and knocked him out in round 3.

Legacy

He was the first undisputed cruiserweight champion and the first man to win a heavyweight title four times. He finished with 44 wins, 29 by knockout, against 10 losses, 2 draws and a no contest. He was inducted into the International Boxing Hall of Fame in 2017. Lennox Lewis, Who’s Who number 29 has named him the best opponent he faced. “I was able to accomplish things no other fighters have,” Holyfield told ESPN in 2017.

31of 39
on the
Who’s Who
Ultimate Boxing Reunion

In the painting

Evander Holyfield

Number 31 of 39 on the Who’s Who list for Ultimate Boxing Reunion by Dean Turner Art, published as Evander Holyfield.

Collectors lean in, argue over faces and pull the names list. Holyfield’s story runs through a lot of this painting: he beat Mike Tyson, Who’s Who number 34 twice, George Foreman, Who’s Who number 35 and Larry Holmes, Who’s Who number 19, and fought Lennox Lewis, Who’s Who number 29 twice.

If you can name every face in this one, there’s a fair chance someone taught you them, maybe a dad who stayed up for the fights.

See Evander Holyfield among all 39 faces in Ultimate Boxing Reunion, a framed canvas print made from Dean’s hand-painted original.

Sources

  1. New Georgia Encyclopedia (Matt Bowers, 7 Jul 2005, edited 6 May 2017), Evander Holyfield: birth, Atlanta at five, Warren Memorial Boys Club, Junior Olympics, Pan American silver, debut, record, last fight in 2011. georgiaencyclopedia.org
  2. ESPN (Dan Rafael, 9 Jun 2017), “I was able to accomplish things no other fighters have”: record, first undisputed cruiserweight, first four time heavyweight champion, his mother, Qawi quote, 2017 induction. espn.com
  3. Olympedia, Kevin Barry: 1984 semi-final disqualification, referee Novičić, bronze. olympedia.org
  4. ESPN (Dan Rafael, 24 Aug 2013), Superfight No. 6, Tyson v Holyfield I: “bullied the bully”, round 6 knockdown. espn.com
  5. Sports Illustrated (Gabriel Baumgaertner, 29 Jun 2012), oral history of the 1997 rematch: Atlas, King and Czyz quotes. si.com
  6. Boxing News (Shaun Brown, 30 Nov 2025), Lennox Lewis names the best he faced (second-hand, citing The Ring). boxingnewsonline.net
  7. CBS News (AP, Mar 1999), Lewis v Holyfield I: cards, crowd, purses, “not the judges”. cbsnews.com
  8. ESPN (Tim Graham, 14 Nov 1999), Lewis v Holyfield II: “I’m not embarrassed by my performance”. espn.com
  9. Boxing News (George Gigney, 6 Nov 2019), On this day, the Fan Man: Bowe II, Steward, delay, crowd, third man to regain the title. boxingnewsonline.net
  10. Seattle Times (AP, 24 Nov 1994), Moorer fight result, majority decision. archive.seattletimes.com
  11. Los Angeles Times (Earl Gustkey, 14 Nov 1992), Bowe v Holyfield I, MIT archive copy: rounds, cards, Cortez, Bowe quote. stuff.mit.edu
  12. UPI (24 Oct 1990), Douglas weighs in at 246. upi.com
  13. Boxing News (9 Nov 2020), How I beat Mike Tyson, by Evander Holyfield: rough tactics, the jab in round 11, last punch of the round. boxingnewsonline.net
  14. ESPN (Nigel Collins, 20 Mar 2013), Boxing’s imperfect marriage: Don Turner’s plan for Tyson. espn.com
  15. Sports Illustrated (Bryan Armen Graham, 22 Jan 2011), Holyfield interview: the Spinks brothers, Olympic team quote. si.com
  16. Fight Freaks Unite (Dan Rafael, 31 Jul 2025), Tommy Brooks notebook. danrafael.substack.com
  17. Referee.com (9 Jul 2020), Tyson v Holyfield II: bites, deductions, disqualification, licence and fine. referee.com
  18. boxingonly.net, Holyfield v Holmes, 19 Jun 1992. boxingonly.net
  19. boxingonly.net, Holyfield v De León, 9 Apr 1988. boxingonly.net
  20. boxingonly.net, Moorer v Holyfield II, 8 Nov 1997. boxingonly.net
  21. boxingonly.net, Bowe v Holyfield III, 4 Nov 1995. boxingonly.net
  22. boxingonly.net, Holyfield v Parkey, 15 May 1987. boxingonly.net
  23. LA Times (Tim Kawakami, 10 Nov 1996), Holyfield stops Tyson in round 11. latimes.com
  24. boxingonly.net, Holyfield v Foreman, 19 Apr 1991. boxingonly.net
  25. boxingonly.net, Holyfield v Ruiz, 12 Aug 2000. boxingonly.net
  26. boxingonly.net, Bowe v Holyfield II, 6 Nov 1993: cards. boxingonly.net
  27. Sherdog (7 Dec 2016), 2017 Boxing Hall of Fame class. sherdog.com
  28. Fox News (23 Jan 2011), Holyfield v Williams ruled a no contest. foxnews.com
  29. Julien’s Auctions, Evander Holyfield vs Chris Byrd fight worn trunks, “WARRIOR” lettering. juliensauctions.com
  30. LA Times, 9 Nov 1997, Holyfield v Moorer II: five knockdowns, Homansky stoppage. latimes.com
  31. UPI, 13 Jul 1986, Holyfield v Qawi I: split decision and cards. upi.com
  32. LA Times, 13 Jul 1986, Holyfield v Qawi I. latimes.com
  33. CBC (AP), May 2011, Holyfield stops Nielsen in Denmark. cbc.ca
  34. Seconds Out (6 Sep 2025), Lewis names the best of his career. secondsout.com
  35. Seconds Out (Kailem Lowe, 5 Dec 2025), Tyson and Bowe name the same man as the best they faced. secondsout.com
  36. Las Vegas Review-Journal (Gilbert Manzano, 9 Jun 2017), Holyfield enters the Hall of Fame: Farhood quote. reviewjournal.com

Names appear exactly as published on the Who’s Who list for Ultimate Boxing Reunion.

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