The best boxing fights that did not happen
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The best boxing fights that did not happen

With a Terence Crawford-Errol Spence fight on the MayPac trajectory, at best, boxing fans are frequently reminded can't-miss fights frequently do not happen. Various stumbling blocks have impeded much-anticipated bouts. Here are the modern era's biggest makeable fights that did not end up taking place.

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25. Evander Holyfield-Vitali Klitschko

Evander Holyfield-Vitali Klitschko
STR/NurPhoto via Getty Images

Wladimir Klitschko was the better prospect and enjoyed a longer reign as heavyweight champion, but the elder Klitschko brother possessed a superior chin and hardly lost a round as a pro. Vitali had Lennox Lewis in trouble, winning on the cards before a cut stopped their 2003 bout. His career lacked a defining victory, however. Holyfield, whose strength of schedule was quite strong, made sense as an opponent in the early 2000s. After Lewis dethroned him as unified champion in 1999, a win over the still-developing WBO champ (Klitschko) would have qualified as significant. An unfortunate Holyfield- John Ruiz trilogy transpired instead.

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24. Ricardo Lopez-Michael Carbajal

Ricardo Lopez-Michael Carbajal
Al Bello/Allsport/Getty Images

Lopez authored one of his generation's best careers, going 51-0-1. "Finito" reigned at strawweight (105 pounds) for most of the 1990s; Carbajal campaigned at light flyweight (108) for much of his career. Despite Carbajal's weight, the American was involved in widely seen bouts with rival Humberto Gonzalez in the mid-'90s. Although Lopez-Gonzalez also qualifies for near-miss status, the Mexican 105-pound champion entered talks with Carbajal for a 1997 fight for the latter's light flyweight belt. Negotiations did not come to fruition, denying Lopez a signature fight that would have elevated the off-radar great's profile. 

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23. Larry Holmes-George Foreman

Larry Holmes-George Foreman
Timothy A. Clary/AFP via Getty Images

Despite being the same age and each remaining heavyweight contenders well past 40, the two legends never fought. When Holmes rose as a contender in the mid-1970s, a post-"Rumble in the Jungle" Foreman was adrift after his title reign ended. He stepped away in 1977, and Holmes took over the division soon after. When Foreman resurfaced 10 years later, Holmes unretired for a Mike Tyson fight. While Foreman-Holmes was agreed to for a 1999 senior-tour-esque fight, prior to finances scuttling the bout, the most realistic would-have-been period for it would have been the early '90s -- when both were high-end contenders past 40.

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22. Oscar De La Hoya-Winky Wright

Oscar De La Hoya-Winky Wright
A. Messerschmidt/Getty Images

It feels strange to include De La Hoya on such a list. His strength of schedule is legendary. "The Golden Boy" took on almost everyone notable from his era and somehow fought Bernard Hopkins and Manny Pacquiao. But he did fight at 154 pounds for several years in the 2000s. A defensive master and one of the great junior middleweights, Wright was a difficult matchup and thus avoided. But De La Hoya indicated an openness to fighting him in 2002. He spent the next two years in the division; no fight transpired. This matchup likely would have catapulted Wright to stardom; the late-blooming fighter moved up in weight in 2005.

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21. Lennox Lewis-Wladimir Klitschko

Lennox Lewis-Wladimir Klitschko
Pavlo Conchar/SOPA Images/LightRocket via Getty Images

Lewis's time as the heavyweight kingpin was winding down when this fight made sense. The younger Klitschko was the WBO champion from 2000-03. Though the WBO belt was not as well-regarded as it is today, the rising prospect and future heavyweight king was a highly rated contender. Their would-be 2001 bout ended up being foiled by Danny Ocean and crew ; that "Ocean's 11"-universe event may or may not have affected Lewis' preparedness for Hasim Rahman, a fringe contender who KO'd him in April 2001. Lewis probably beats the pre-Emanuel Steward Wladimir, but the Steward-trained Lewis did have a tough time against Vitali Klitschko in his final bout.

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20. Wilfred Benitez-Pipino Cuevas

Wilfred Benitez-Pipino Cuevas
The Ring Magazine via Getty Images

This battle of historically precocious champions would have taken place in the late 1970s. Benitez became the youngest champion in boxing history, winning a 140-pound title at 17. A year later, Cuevas claimed the WBA welterweight strap at 18. Both were champions throughout the late '70s, and Benitez moved up to Cuevas' 147-pound division in 1977 and won the WBC belt in January 1979. This boxer-vs.-puncher unification matchup and quality chapter in the storied Puerto Rico-Mexico rivalry did not materialize. The two ended up dropping their respective belts to future icons Sugar Ray Leonard and Thomas Hearns, respectively. 

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19. Johnny Tapia-Mark Johnson

Johnny Tapia-Mark Johnson
Holly Stein/Allsport/Getty Images

The boxing world missed a rare all-American flyweight battle 20-plus years ago. Johnson came up in an intriguing era. The likes of Michael Carbajal, Humberto Gonzalez, Danny Romero, and Tapia campaigned at and around 112 pounds during this period. Johnson could not land a fight with any. A fellow Hall of Famer, Tapia held a 115-pound belt for a few years but left the division when "Too Sharp" entered it in 1999. Johnson was a top-10 pound-for-pound regular in the late '90s; Tapia surged to that level after beating Romero in an all-New Mexico duel in 1997. This fight would have peaked then, but Johnson was unable to land it.

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18. Floyd Mayweather Jr.-Paul Williams

Floyd Mayweather Jr.-Paul Williams
Robyn Beck/AFP/Getty Images

Known to cherry-pick, Mayweather delaying matchups with Manny Pacquiao and Shane Mosley is a bigger boxing sin. But he did not face Williams, opting to fight multiple no-hopers during his early welterweight years. In Mayweather's defense, other big names were not eager to face Williams either. Not quite an A-lister, Williams would have posed an issue for Mayweather. The 6-foot-1 southpaw with a 79-inch reach took Antonio Margarito's welterweight belt in 2007. After big fights with Oscar De La Hoya and Ricky Hatton, Mayweather staged a near-two-year retirement. Williams moved up in weight in 2008 and was tragically paralyzed in a 2012 motorcycle accident. 

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17. Pernell Whitaker-Ike Quartey

Pernell Whitaker-Ike Quartey
Focus on Sport/Getty Images

Quartey resided as a top-five welterweight for five-plus years in the 1990s. For a chunk of this period, Whitaker resided as the pound-for-pound king; the historically gifted defender snatched that claim from Julio Cesar Chavez in 1993. Whitaker campaigned at welterweight from 1993-99 and held the WBC belt for much of that stretch. Quartey, who won the WBA's 147-pound strap in 1994, could not book a unification fight with Whitaker. Talks did commence for a 1998 fight, but "Sweet Pea" was in decline by then. And said talks broke down. The Ghanaian ended up losing a split decision to Oscar De La Hoya in 1999.

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16. Thomas Hearns-Mike McCallum

Thomas Hearns-Mike McCallum
The Ring Magazine via Getty Images

Hearns waged legendary battles at welterweight and middleweight -- against Sugar Ray Leonard and Marvelous Marvin Hagler -- but his best weight may have been 154 pounds. Hearns smashed Roberto Duran at junior middleweight in 1984 and fought there from 1981-86. McCallum was the division's other beltholder for most of that stretch. While "the Body Snatcher" fought big names in the 1990s -- Roy Jones Jr., James Toney -- he could not get one of the 1980s' "Four Kings" in the ring. A mid-'80s fight against his former Kronk Gym stablemate would have provided a chance for McCallum to claim his top win and a chance at another quality victory for Hearns, who moved up in 1987.

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15. Roman Gonzalez-Naoya Inoue

Roman Gonzalez-Naoya Inoue
Joe Camporeale-USA TODAY Sports

Both are still active, but this fight will not take place. Gonzalez, whom most viewed as the No. 1 pound-for-pound fighter following Mayweather's 2015 retirement, has resided at 115 pounds since 2016. During that time, "Chocolatito" has engaged in a storied round-robin with Juan Estrada, Srisaket Sor Rungvisai, and Carlos Cuadras. The fearsome-punching Inoue spent three-plus years in this division (2014-17) and held a belt throughout but moved to bantamweight without facing Gonzalez or his rivals. The younger Inoue passing through this stacked division without facing its A-listers was a missed opportunity for boxing.

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14. Sergio Martinez-Gennadiy Golovkin

Sergio Martinez-Gennadiy Golovkin
Joe Camporeale-USA TODAY Sports

Martinez was correct to avoid Golovkin. The Kazakh destroyer would have bulldozed the aging middleweight champ when the fight was discussed (2013-14). Knee issues and age did in the slick Argentinian southpaw by then. But both GGG and "Maravilla" won middleweight belts in 2010; Golovkin, however, did not come to the States until 2012. GGG loomed throughout Martinez's four-year reign, and while the eight-year middleweight champ is seven years younger than Martinez, GGG was eager to face Canelo Alvarez despite their eight-year age gap. An early-2010s fight between Golovkin and agile Martinez would have been a must-see for boxing purists.

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13. Prince Naseem Hamed-Juan Manuel Marquez

Prince Naseem Hamed-Juan Manuel Marquez
Adam Davy/EMPICS via Getty Images

One of boxing's top stars in the late 1990s, Hamed ruled the featherweight division for years. A formidable cadre of opponents -- Marquez, Marco Antonio Barrera, and Erik Morales -- entered the 126-pound division during Hamed's reign. Marquez served as the unorthodox showman's mandatory challenger around 2000. While the famed counterpuncher was years away from his peak, he is one year older than Hamed. Blessed with a unique skillset and punching power that attracted big audiences to the small weight class, Hamed opted for a different path. But injuries and a humbling 2001 loss to Barrera ended his career by age 28.

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12. Floyd Mayweather Jr.-Kostya Tszyu

Floyd Mayweather Jr.-Kostya Tszyu
Andrew Couldridge/Action Images/Icon Smi

Mayweather's stay at 140 pounds was brief, potentially because of that division's longtime alpha. Tszyu joined Mayweather atop pound-for-pound rankings in the early 2000s. Each was a borderline top-three fighter in 2004, even though the feared Australian -- the junior welterweight champ for nearly a decade -- was 35 by this point. After four years at lightweight, Mayweather fought just three times at 140. Tszyu saw his three most lucrative opponents -- Mayweather, Oscar De La Hoya, and Shane Mosley -- pass through his division without facing him. Mayweather faced weak opposition at 140 before leaving the division in 2005.

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11. Sergey Kovalev-Adonis Stevenson

Sergey Kovalev-Adonis Stevenson
Joe Camporeale-USA TODAY Sports

The light heavyweight fight to make for several years became difficult to finalize when Stevenson moved from HBO to Showtime. Stevenson backed out of a deal to face Kovalev on HBO, heading over to the then-boxing leader's rival network. Stevenson became the lineal 175-pound champ after a first-round KO of Chad Dawson in 2012, but Kovalev loomed as a menacing challenge. The Russian puncher fought a 49-year-old Bernard Hopkins instead in 2014 but could not get Stevenson in the ring. Kovalev lost the lineal title to Andre Ward in a disputed 2016 decision; Stevenson was content to keep his belt via lower-profile fights.

Roy Jones Jr.-Dariusz Michalczewski
John Iacono/SI/Icon Sportswire

Unmatched in his prime, Jones does not have many big names on his resume during his 175-pound stay. Michalczewski, a Polish fighter who camped in Germany during his prime, loomed as his top challenger for several years in the late 1990s and early 2000s. The would-be Jones foe held the WBO light heavyweight belt for nearly a decade, after dropping from cruiserweight. Almost all those title defenses came in Germany, however, and neither he nor Jones desired to leave their home turf for a fight. This 175-pound unification simmered for longer than Kovalev-Stevenson. Jones and Michalczewski were done as champs by 2004, losing their belts in a seven-month span.

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9. Riddick Bowe-Mike Tyson

Riddick Bowe-Mike Tyson
The Ring Magazine/Getty Images

For a short period in the 1990s, Bowe was the man to beat at heavyweight. The 6-foot-5 fighter took the lineal title from Evander Holyfield in 1992 and beat him in their 1995 rubber match. Bowe's peak, however, came during Tyson's three-plus-year prison sentence. Tyson also said during a 1994 interview he did not expect to fight Bowe; the two were once classmates at a Brooklyn elementary school. This would have been a bigger issue had Tyson not gone to prison, but both fighters' stars faded in 1996. Holyfield knocked out Tyson, and Bowe was losing on the cards in both Andrew Golota fights (pre-low blows). Bowe left the sport for eight years in 1997.

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8. George Foreman-Earnie Shavers

George Foreman-Earnie Shavers
Bettmann/Getty Images

Two of the sport's great punchers competed during the heavyweight division's premier period, and even though Shavers is five years older than Foreman, his route to boxing's upper reaches took longer. This fight would have made sense only for a short time in the mid-1970s when Shavers was driving his late-blooming career toward a title shot. But Foreman left the sport in 1977, taking this bout off the table. Shavers pushed Muhammad Ali to the limit that year and later joined Foreman in knocking out Ken Norton early, but the most tantalizing fights for him -- against Foreman and Joe Frazier -- did not come together.

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7. Joe Frazier- Ken Norton

Joe Frazier-Ken Norton
The Ring Magazine/Getty Images

Two of the greats at heavyweight boxing's 1970s zenith, both Frazier and Norton fought trilogies with Muhammad Ali. Each beat Ali once, and many argue Norton deserved at least one more win in that series. Frazier and Norton also each fought Foreman, proving poor stylistic matchups for the terrifying puncher, but they never matched up in this round-robin of sorts. This miss is rather straightforward; the two were close friends and preferred not to meet up in what would have been a fascinating fight.

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6. Shane Mosley-Felix Trinidad

Shane Mosley-Felix Trinidad
Icon Sports Media

Going into 2001, Mosley and Trinidad ranked first and second on Ring Magazine 's pound-for-pound list. Both were flush with momentum after beating Oscar De La Hoya, with Mosley's win more convincing than Tito's. Rather than taking a superfight with Mosley, who lobbied for such a bout, Trinidad set his sights on a move to middleweight. Mosley-Trinidad would have been a massive event in late 2000 or 2001. Instead, Tito climbed to 160 pounds and saw Bernard Hopkins derail his career. Vernon Forrest dimmed Mosley's star shortly after, though "Sugar Shane" recovered. The boxing world lost out when the unbeaten champs went their separate ways.

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5. Juan Manuel Marquez-Erik Morales

Juan Manuel Marquez-Erik Morales
Aaron M. Sprecher/Icon Sportswire

This century's best round-robin came when Marquez, Morales, Marco Antonio Barrera, and Manny Pacquiao fought a combined 13 times from 2000-2012. However, an all-Mexico war between Morales and Marquez is absent from this bracket. Despite being three years younger, Morales beat Marquez by six years to a major belt. But both were contenders by 1996 and stayed in or around the same division for over a decade. It was somehow 2011 before the two agreed to fight. Even that fizzled. With Morales peaking early and Marquez's best stuff coming in his 30s, an early- to mid-2000s featherweight fight would have been a pay-per-view event. 

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4. Lennox Lewis-Riddick Bowe

Lennox Lewis-Riddick Bowe
Allsport UK/Getty Images

Lewis beat every pro fighter he faced, but a big (no pun intended) name is absent from the Brit's resume. Bowe-Lewis is the 1990s' defining miss. Lewis defeated Bowe in the 1988 Olympics' super heavyweight gold-medal match, but "Big Daddy" beat him to pro stardom by taking Evander Holyfield's lineal title in 1992. A promotional stunt had Bowe throw one of his belts in the trash rather than face mandatory challenger Lewis. They were back on track to fight in 1994 and '96, however. Oliver McCall's upset win over Lewis and Bowe opting to step away from the sport after his Andrew Golota experiences -- which showed a decline -- buried the bout for good.

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3. Mike Tyson-George Foreman

Mike Tyson-George Foreman
Bettmann/Getty Images

An under-discussed period in Tyson's career: the early-1990s stretch in between his Buster Douglas loss and a career-changing prison sentence. That period proves relevant here because Foreman entered the picture as a Tyson rebuild/cash-cow opponent. Fearful of how his style would match with the larger Foreman's, a picking-up-the-pieces Tyson preferred to go in another direction for his 1990 recovery period. "Iron Mike" fought Henry Tillman, Alex Stewart, and Razor Ruddock before prison, while Foreman soon pushed champion Evander Holyfield. A lesser Tyson could have challenged then-champion Foreman after prison, but he was rebuilding his profile by that point.

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2. Roberto Duran-Alexis Arguello

Roberto Duran-Alexis Arguello
The Ring Magazine via Getty Images

By 1977, Arguello -- a former featherweight champion -- claimed a 130-pound belt. The Nicaraguan legend also fought a few times at lightweight over the next two years, potentially preparing for a battle with Duran, the greatest lightweight in boxing history. While talks of this clash did take place, Duran was wrapping up his 135-pound run by this point. "El Cholo" was done in the division by 1978 and ended the 1980s at middleweight. Duran-Sugar Ray Leonard I -- a ferocious Duran outing -- and Arguello-Aaron Pryor I -- the fight of the '80s -- showed what kind of action-crazed event this would have been had Duran stayed at 135 a bit longer.

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1. Sugar Ray Leonard-Aaron Pryor

Sugar Ray Leonard-Aaron Pryor
Bettmann/Getty Images

The relentlessness Pryor displayed against Arguello created the ultimate modern boxing near-miss. Despite Pryor coming up while Leonard, Duran, and Hearns fought at welterweight, the tenacious junior welterweight did not score a fight with any of them as a pro. While prior Leonard-Pryor negotiations broke down over low offers to the less famous fighter, the two reached an agreement to vie for Leonard's welterweight belt in 1982. Leonard soon suffering a detached retina in a tune-up fight threw off those plans. "Hawk" moved on to Arguello later that year, but Leonard's first retirement took a fight with boxing's star of the moment off the table, altering Pryor's career.

Sam Robinson is a Kansas City, Mo.-based writer who mostly writes about the NFL. He has covered sports for nearly 10 years. Boxing, the Royals and Pandora stations featuring female rock protagonists are some of his go-tos. Occasionally interesting tweets @SRobinson25.

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