This past weekend, news broke that Jaron “Boots” Ennis offered a six-figure contract to face Charles Conwell at super welterweight. A fighter known for his explosive speed and knockout power, Ennis (31-0-0 28 KOs) has been carving a path through the welterweight division, but the move to challenge Conwell raised some eyebrows. Conwell, who refers to himself as boxing’s “best-kept secret,” has been quietly building his resume and sharpening his skills. As we highlighted in a recent article, Conwell (18-0-0 13 KOs) is a force to be reckoned with in the division, even if his star power hasn’t yet matched his talent.
For Ennis, this could have been one of the most significant tests of his career. Charles Conwell is not just another opponent; he’s a skilled boxer with a style that can make even the most aggressive fighters second-guess themselves. It’s easy to applaud Ennis for even extending the offer, given the potential difficulty in preparing for a fighter as underappreciated as Conwell. However, the offer raises an intriguing question: how much was Boots willing to risk?
Just recently, Brian Norman Jr. turned down $1.5 million to fight Ennis, instead demanding a purse north of $2 million. This shows a consistent trend in how top-tier, yet underappreciated, fighters are approached. Whether they are considered “boring,” too dangerous, or lacking marketability, many talented boxers are consistently lowballed or relegated to the B-side of negotiations. Let’s take a closer look at some of the names that have struggled under similar circumstances—fighters who had to claw their way to a title to even be considered as viable opponents.
Demetrius Andrade: A Career Derailed by Politics
Demetrius “Boo Boo” Andrade (32-0-0 19 KOs) is one of the most frustrating cases of boxing talent being underappreciated. His journey to the top has been riddled with missteps and promotional nightmares that have often kept him out of the limelight. The most notable setback came in 2015, when Andrade, then the WBO super welterweight champion, got involved in a complicated legal battle with his promoters, Star Boxing and Banner Promotions. Seeking better financial terms, Andrade turned to Jay-Z’s Roc Nation Sports, a move that was supposed to elevate his career to new heights. But things didn’t pan out.
Andrade was slated to defend his title against Jermell Charlo, but the negotiations with Roc Nation fell apart. Andrade pulled out of the fight, and Star Boxing, along with Banner Promotions, filed a breach of contract lawsuit that effectively shelved him for over a year. During that time, Andrade lost his WBO title due to inactivity, and his career took a hit that he has been struggling to recover from ever since. Roc Nation, despite their best efforts, couldn’t finalize a deal, leaving Andrade to return to his old promoters and salvage what was left of his prime fighting years. This period of inactivity severely damaged his reputation and robbed him of some of his best years in the ring.
The Ramifications of Negotiations
The ripple effects of this debacle didn’t end there. Andrade was supposed to have his breakout moment against Billy Joe Saunders in 2018. The fight was scheduled, press conferences were held, and Andrade even dressed up in colonial-era attire to promote the bout in Boston. But Saunders tested positive for a banned substance just weeks before the fight. Once again, Andrade’s shot at the big time was snatched away.
Despite these setbacks, Andrade has continuously called out fighters like Jermall Charlo, Gennady Golovkin, and Canelo Álvarez. However, his promotional issues and lack of star power have kept these big names at bay. Whether it’s a result of his Roc Nation fiasco or simply bad timing, Andrade remains one of the most talented yet underappreciated fighters in boxing. His story transitions into a broader issue faced by other defensive fighters like Guillermo Rigondeaux.
Guillermo Rigondeaux: A Defensive Master Labeled ‘Boring’
Guillermo “El Chacal” Rigondeaux (20-3-0 13 KOs) is often regarded as one of the greatest defensive tacticians the sport has ever seen. The Cuban southpaw, a two-time Olympic gold medalist, brought his immense technical prowess to the professional ranks. However, instead of being celebrated, Rigondeaux was quickly labeled “boring” due to his cautious, counterpunch-heavy style. Even his promoter, Bob Arum, openly criticized Rigondeaux’s fights for their lack of action, stating that they were difficult to sell to a mainstream audience.
As a result, Top Rank rarely prioritized promoting Rigondeaux, despite his immense talent and championship pedigree. He was frequently avoided by top fighters, especially during his prime, when he held the WBA Super Bantamweight title. His most notable victory came against Nonito Donaire, a fight that should have solidified his position as one of the pound-for-pound best. Rigondeaux outclassed Donaire, winning a clear decision to become the lineal and unified super bantamweight champion. Despite his dominance, Rigondeaux was paid considerably less than Donaire, a clear reflection of his struggle to gain widespread popularity.
A Desperate Gamble for Marketability
The avoidance didn’t stop there. Leo Santa Cruz and Carl Frampton both steered clear of Rigondeaux. Rigondeaux’s team claimed they avoided him because of his lack of drawing power. Eventually, in an attempt to find a meaningful fight, Rigondeaux moved up two weight classes to face Vasiliy Lomachenko. Rigondeaux earned a reported $400,000 for the bout, while Lomachenko made $1.2 million—a clear indication of the financial disparities Rigondeaux faced throughout his career. The fight itself was anticlimactic, as Rigondeaux retired on his stool after six rounds. Although he wasn’t taking significant punishment, he was thoroughly outboxed. This disappointing end further cemented Rigondeaux’s reputation as a difficult, albeit not marketable, fighter.
Rigondeaux’s career mirrors the struggles of other technically gifted fighters who lack the fan-friendly styles that drive pay-per-view numbers. This trend is evident when looking at fighters like Pernell Whitaker, another defensive genius who faced similar challenges.
Pernell Whitaker: A Defensive Icon Lost in the Shadows
Pernell “Sweet Pea” Whitaker (40-4-1 17 KOs) is often considered the epitome of defensive mastery in boxing. A gold medalist at the 1984 Olympics, Whitaker transitioned into the professional ranks and won his first world title in 1989. Known for his ability to slip, duck, and make opponents miss with dazzling ease, Whitaker’s skills in the ring were second to none. Despite his undeniable talent, he never reached the financial heights of his more action-oriented peers.
In an era dominated by fighters like Julio César Chávez and Meldrick Taylor, Whitaker’s defensive prowess wasn’t enough to draw massive paydays. One of his most infamous moments came when he faced Chávez in Texas. Chávez was an undefeated legend at the time, boasting an 87-0-0 record. Most observers believed Whitaker had done enough to win the fight, yet the judges ruled it a controversial draw. Sports Illustrated even ran a cover story titled “Robbed!” Whitaker may have gained critical acclaim, but financial success eluded him throughout his career.
Whitaker’s most high-profile fight came against the rising star Oscar De La Hoya. Many believed that Whitaker outboxed the younger fighter, but De La Hoya was awarded a controversial unanimous decision. This loss further contributed to the narrative that Whitaker’s style, while technically brilliant, wasn’t appealing enough to sway judges or captivate audiences.
Much like Rigondeaux and Andrade, Whitaker’s career was marked by a lack of major financial success despite his undeniable talent. Another fighter who faced similar struggles early in his career was Juan Manuel Marquez, a fighter whose perseverance eventually led to legendary status.
Juan Manuel Marquez: From Underdog to Mexican Legend
It’s hard to imagine now, given his legendary status, but Juan Manuel Marquez (56-7-1 40 KOs) entered his first fight against Manny Pacquiao with his career hanging by a thread. Unlike his fellow Mexican warriors Erik Morales and Marco Antonio Barrera, Marquez was more of a technician and counterpuncher. His style wasn’t as flashy or aggressive, which made it difficult for him to break through into the upper echelons of the sport during the early 2000s.
After winning the WBA featherweight title, Marquez was stripped of the belt for refusing to take on a mandatory defense. Even as the IBF champion, he struggled to land high-profile fights. When he finally secured a bout with Pacquiao, many believed Marquez was overmatched. Pacquiao, fresh off a knockout win over Barrera, knocked Marquez down three times in the first round. But Marquez displayed incredible heart, battling back to earn a controversial split decision draw.
For many, that fight marked the turning point in Marquez’s career. He went from being an afterthought to a bona fide star in the sport, eventually becoming one of the greatest Mexican fighters of all time.
Sometimes, boxing does have a happy ending. But it’s clear that for many talented fighters, getting to that point requires overcoming more than just opponents in the ring.