The Man in the Middle: Roberto Diaz on the art of matchmaking

ROBERTO Diaz left Golden Boy Promotions having, as one of the world’s leading matchmakers, long been so crucial to their success. During a potentially defining time in their short promotional history, his influence can perhaps even still be felt. By Declan Warrington.

The fight between Saul “Canelo” Alvarez and John Ryder, in Guadalajara on Cinco de Mayo weekend last year, came weeks after Roberto Diaz had suffered a heart attack, and yet the respected matchmaker was ringside – watching, and absorbing – having travelled from Los Angeles to be present.

His wife Carla, who had been employed by the world’s top fighter for a long time, accompanied him there. Several weeks later, he observed from a distance as Jaime Munguia narrowly defeated Sergiy Derevyanchenko, his curiosity piqued due to his significant involvement in Munguia’s journey before Diaz left Golden Boy Promotions earlier in 2023.

After 15 years with Golden Boy, he had established himself as one of the top matchmakers globally and a crucial figure in a promotional organization that was once deemed the most influential worldwide. Ryan Garcia’s recent triumph over Devin Haney has further solidified their interests, surpassing the potential impact of Munguia defeating Alvarez or Vergil Ortiz Jr. prevailing against Tim Tszyu. However, even with these victories, it is unlikely that they will reach the same heights as before, when the allure of super fights and the presence of boxing legends like Oscar De La Hoya, Bernard Hopkins, Shane Mosley, Ricky Hatton, and others made them truly exceptional.

Diaz played a crucial role in connecting Hatton with De La Hoya and Schaefer, thanks to his close relationship with Barrera. This connection paved the way for the highly-anticipated fight between Hatton and Mayweather, who had previously defeated De La Hoya in a Golden Boy event. Ultimately, Diaz’s involvement ensured that the two biggest fights of 2007 belonged to Hatton and Mayweather.

Marco Antonio Barrera, a renowned figure in the A-list association, captured in a captivating photo by Stephanie Trapp/TGB.

Barrera played a significant role in introducing Diaz to Golden Boy and other fighters, leading to the growth of his reputation. However, after his separation from the Mexican, Diaz’s influence may not be as prominent as before, much like Barrera, De La Hoya, Hopkins, and Schaefer. Nevertheless, Diaz, like many others who collaborated or competed with him, will always be aware of the significant role he played in making numerous thrilling fights happen.

To truly understand Diaz’s 55-year journey, one must delve into the significant events that occurred long before his encounter with Barrera. This includes exploring the influence of gang culture in his birthplace of San Francisco, and his father’s decision to uproot him to the unfamiliar Yucatan region of Mexico. Additionally, it entails examining his various roles as a salesman and parole officer, as well as the life-altering car accident he survived and his triumphant fight against cancer, which ultimately saved his marriage thanks to Carla’s unwavering commitment during a time when divorce seemed imminent.

Diaz’s recent health scare and departure from Golden Boy have likely given him a heightened perspective. He acknowledges that at times, he neglected his family while pursuing his “dream.” It is possible that the demands of his profession and the rapid growth of Golden Boy made it inevitable for things to have unfolded that way.

“That’s what I learned after the 15 years when we parted ways,” he tells Boxing News from his home in LA. “Another message is first is your health; second is your family, and third is your job, because your job’s always going to be there as long as they need you. Family has to be there.

“I don’t want to come across as regretful, because my choices have shaped who I am today and brought me to where I am. However, it is important to prioritize your family, and there were instances where I had to decline certain commitments due to work obligations. For example, during the [Barrera] fight, I was in training camp while my father [Roberto] had been battling illness for three decades. My family relies on me, and I needed to be present for them. I had planned to visit my father once the fight was over, but sadly, he passed away on the morning of the event. If only I had one more day, I could have seen him. Everyone close to us, including Marco and his family, was aware of the situation. After the fight, I immediately rushed him to get stitches for his cut. When we returned to the hotel, the atmosphere was somber. I turned around to find Carla in tears. It was then that I realized my father had passed away. Looking back, it is clear that my job always took precedence.”

Barrera’s belief in Diaz grew stronger after their initial encounter at a shopping center in San Diego, where Diaz resided at the time. This belief was further solidified when Diaz fought Cesar Najera at Fantasy Springs, ultimately leading to an invitation to join Barrera’s training camp in Big Bear, California, for their memorable first bout against Erik Morales. Diaz’s dedication and performance in that fight played a significant role in the timing of their trilogy’s third match. As a result, Barrera emerged victorious once again over his biggest adversary, boosting Diaz’s reputation and eventually leading to an offer to become Eric Gomez’s assistant matchmaker.

During my probation, I followed a routine of working for a week and then taking a week off. I would head up to the camp and spend a couple of days there, joining in their activities, and sharing meals with them,” he reminisces. “Over time, I went from being a mere fan to becoming their friend. One day, my friend suggested, ‘Why don’t you carry the flag for my next fight?’ And that marked the beginning of an incredible trilogy between us.”

“I made the decision to sign with Golden Boy Promotions, led by Oscar De La Hoya. At that time, the company was just starting out and Marco, apart from De La Hoya, was their most prominent fighter. Our first fight was against Manny Pacquiao, and during our training in Big Bear, I noticed that Pacquiao, although young and quick, struggled with Marco’s powerful southpaw jab. Comparatively, I didn’t see anyone better than Naseem Hamed, who was more unorthodox and had a stronger punch. Looking back, Marco turned out to be an incredible fighter, one of the best in history, a rare talent that emerges only once in a century. However, at that moment, he didn’t appear to be anything extraordinary.”

After his defeat, I felt like it was the end for him. Neither Oscar nor Golden Boy dropped him. However, they decided to give him another chance. From that moment onwards, it was up to me. I witnessed Erik Morales face two of his most challenging battles the following year, and it struck me that Marco had to fight him for the third time. I never questioned my decision for that fight. Ultimately, that victory was what truly established Golden Boy’s reputation.

If we take a step back and consider the opinions of the majority of fans, they would likely argue that Juan Manuel Marquez was the top-ranked boxer. They might also mention Marco Antonio Barrera as the second best, given his victories over Morales. As for Morales, he would probably be seen as the third best, despite the undeniable outcomes. However, personally, I would almost argue that Morales should be considered number one, followed by Marco at number two, and Marquez at number three.

“Don’t forget, I’m here with Marco. ‘Let’s wrap it up for today.’ He’s a partner at Golden Boy, so we should prioritize the promotion and the young kids. However, he had different intentions [as he fought against Pacquiao again in 2007, and unfortunately lost]. That’s the true essence of a fighter, always staying true to themselves.”

The even-more-transformative decade and a half began with Golden Boy, marking the evolution of the promoter’s reputation from collaborating with established champions to nurturing them from the beginning. Diaz made the move from Sacramento to LA to join Gomez’s team, leaving his family behind. However, after overseeing the first two promotions, he contemplated giving up.

“He exclaimed, ‘Oh my god! They expanded overnight, which made it feel like a crash course. It was sink or swim. When Bernard Hopkins beat Kelly Pavlik, it was an incredible time. Everyone wanted to be part of Golden Boy. There used to be a criticism about Golden Boy that if you were already a star, that’s where you would go. ‘But don’t go as a young fighter because they don’t know how to develop them.’ They had Mosley, Hopkins, Marquez, Barrera; established fighters who were nearing retirement but had never produced a world champion. However, that criticism disappeared a few years later with the emergence of Abner Mares, Daniel Ponce de Leon, Danny Garcia, Adrien Broner, Deontay Wilder, and Jermell Charlo. I take immense pride in it because I kickstarted the careers of many of them. I handled almost 99 percent of Wilder’s fights.”

It wasn’t all smooth sailing, as I recall receiving a harsh email blaming me for Victor Ortiz’s defeat against Marcos Maidana. That experience taught me the importance of having resilience. When the fighters, team, or promoter succeed, they receive all the credit, but if they lose, it’s the matchmaker who gets blamed. It was a demanding and exhilarating job, but not something the average person could handle. There were even weekends with three shows, highlighting the relentless pace of that period.

Richard did an exceptional job. Looking back, I now understand what Richard perceived back then. Perhaps I didn’t have the same clarity. “Maybe that’s what he noticed and disliked.” However, I don’t believe that Richard and Oscar parting ways is the reason behind the company’s transformation. The Yankees had their time as the top team. It’s a natural part of progress and development. This phenomenon occurs much more frequently in boxing.

The notion of a flawless show is nonexistent; there will invariably be some mishaps. Nevertheless, one must carry on with the performance.

According to Diaz, Richard Schaefer did an excellent job.

Golden Boy is in the process of rebuilding with Garcia, and possibly Munguia and Ortiz. Diaz experienced heartache in the past, particularly with Hatton’s loss to Mayweather. He also had a fallout with Barrera but has since moved on. Diaz also witnessed Gomez’s wasted talent. However, the withdrawal of HBO from boxing was a significant blow for Diaz and his colleagues.

According to the Mexican, the split between De La Hoya and Schaefer significantly affected the pace of progress. This was mainly because the prominent figure in their roster was “Canelo” and he chose to stay loyal to Golden Boy while other fighters departed. Many of these fighters were not tied by contracts and as they left, so did the networks associated with them. Fortunately, HBO managed to secure a long-term deal with Canelo, which provided some relief for a while.

HBO’s sudden decision to exit the boxing scene was a massive blow to everyone involved – the fighters, promoters, and the sport as a whole. Despite this setback, many still find solace in revisiting and reliving the old fights broadcasted by HBO, as they were truly the pinnacle of boxing coverage. In my role, I had a significant connection with the fighters on a personal level. While others may have also provided support, the fighters knew they could always count on me, just a phone call away. I wanted to remain involved and maintain close relationships with them. Unfortunately, we had to part ways with some champions, even though they were promised otherwise. The unexpected emergence of Covid-19 and its subsequent impact on the world was beyond anyone’s anticipation.

After Alvarez left, Golden Boy partnered with DAZN. If Diaz had not declined to guarantee a match between Alvarez and Dmitry Bivol, he thinks they would have promoted the talented Russian, whom he recognized as having great potential. Diaz was present in Las Vegas for the Bivol-Alvarez fight in 2022 and when he watches the Alvarez-Munguia fight, he will be far from impartial. Just last June 2023, Diaz arranged for Danielito Zorrilla to replace the injured Liam Paro as Regis Prograis’ opponent.

He speaks, “It took fifteen years. It was a challenge, as people got used to associating my name with Golden Boy. However, my contract reached its conclusion, as every new chapter eventually does. It was time for both parties to part ways; perhaps in the future, details will slowly surface. The way things ended may not have been ideal, or at least not handled properly. Despite that, I have no regrets about the fifteen years I spent there – the first fourteen and a half were truly incredible.”

I have a deep understanding of the inner workings of matchmakers, as only fellow matchmakers can truly comprehend each other. My passion lies in boxing, and I am determined to remain a part of it. It’s what I excel at and what brings me fulfillment. However, I yearn to take on a different role within the boxing world. I desire to step back, offer guidance, and contribute here and there as an advisor.

I have gained a perspective from both angles now. It’s not solely about being a manager who demands higher pay. I understand the importance of finding a middle ground.