The Execution and Strategic Keys to Matchmaking Success
March 3, 2022
Anthony Saldana (143 articles)

The Execution and Strategic Keys to Matchmaking Success

By Anthony “Stacks” Saldaña

For this writer what makes boxing the Sweet Science isn’t two guys slugging it out in a Rock-’em Sock-’em Robot scenario. It’s seeing some real skill and artistry in the ring, the ebb and flow. For others it’s watching a fight that they know will be explosive and entertaining. A match with razzle and dazzle. No matter what style you like, one thing is clear, a special fighter is one that can bridge all the different categories and become a figure that everyone can appreciate. Boxing is a truly a global sport. From Mexico to Japan and everywhere between, from backyard So. Cal fight parties with Modelo’s and Carne Asada, to Wembley Stadium and 90,000 electric fans, it’s boxing that’s brought them together. A top pay-per-view fight can generate a revenue in the hundreds of millions of dollars. With so much money involved, is it any wonder that the competition for top fighters and great matches is cutthroat and often very intense? Well there are many pieces to the puzzle when it comes to building a successful boxing event including one of the most important. The person in the shadows. The person that is never in the public eye and the person who keeps the fans coming back time after time. The person who is solely and personally responsible for the purse, the development of fighters and the execution of implementing an entertaining fight card. Who is this person you ask? The matchmaker. The person whose job it is to develop his promoter’s fighters while at the same time accomplishing the true goal of making action-packed fights that will entertain the fans. 

Charles Bosecker sits behind his computer waiting to solidify an upcoming bout for 360 Promotions. Photo by Gustavo Olmedo Jr.

This writer recently sat down with 2x matchmaker of the year Charles “Chuck” Bosecker to get an in-depth look at the importance of his role in the sport. Chuck was born and raised in “The OC” and throughout his high school years bounced around from school to school. “ I wasn’t the best student and did what young guys do, I ended up in continuation and then home schooled, but my senior year I buckled down and graduated.” Stated Bosecker. After he graduated Bosecker took up martial arts and studied several disciplines including Taekwondo, Hapkido, Brazilian Jiu Jitsu and although he was an avid combat sports fan, he never was a boxing fan.

Then in 2006 while helping out his grade school friend and professional boxer Paul Velarde line up fights Bosecker’s life would slowly begin to change forever. “I met Whitfield Haden and just asked him a million questions about matchmaking and before you know it I was his bookie, helping him book opponents for fighters.” Stated Bosecker. The job and understanding of the dynamics of matchmaking however was a very slow frustrating process. Bosecker would bring potential opponents to Haden for his fighters and would get shot down. “When I started I was just basically going door to door at gyms trying to setup fights and would get looked at like, “Who the Fuck are you?” “Then when I did get guys that wanted to fight Haden would say “Nope” so it was very discouraging. I would go to bed at night and ask myself what the fuck am I doing.” As the frustrations continued to build up on Bosecker, the doors of matchmaking would start to open. Bosecker was getting his name recognized in the boxing scene and before he knew it, his partnership with Haden would lead to Bosecker matching fights for the likes of Golden Boy Promotions and Top Rank Boxing. Bosecker would also begin to advise fighters and then was given the opportunity to become the head matchmaker for Roy Englebrecht. 

Charles Bosecker poses with Trainers Ben Lira, Abel Sanchez and Ruslan Madiyev

While matchmaking for Englebrecht, Bosecker would also get the opportunity to meet and matchmake fighters from other promotional companies. “I worked for Roy but several different promotional companies including Mayweather Promotions, Golden Boy and others would buy slots on the show and that’s where I met Tom Loeffler.” Said Bosecker.  A business relationship between Loeffler and Bosecker would develop and in 2018 Loeffler would begin to use Charles as his personal matchmaker. By that time Bosecker had his name deeply engraved in the Southern California boxing scene having matched the likes of Seniesa Estrada, Dmitry Bivol, Arnold Barbosa Jr., Ryan Garcia, Kenia Enriquez and match made the last ever HBO Boxing show that was held at the Stubhub Center. 

Dmitry Bivol takes questions from the media ahead of his upcoming super fight with Canelo Alvarez Photo courtesy of DAZN

HBO Boxing’s Last Fight Card Poster

It’s said that the matchmaker has to find the “right fighters to make the right fights,” a term that is somewhat puzzling and definitely a task that is easier said than done. But Bosecker’s job doesn’t scratch the surface there. As the matchmaker he has to follow up to make sure his matches are solid, make sure the fighters get to town, their motel and to the venue. Many times he’s in charge of setting up the weigh-in, acts as a liaison between his employer and the boxing commission, then he has to worry that no-one pulls out of the match so it’s really an ongoing venture until they step into the ring. Then comes the night of the fight and he is usually found running around the venue making sure everything goes as planned. A job I don’t envy. Sometimes in boxing however fights do manifest themselves, especially when sanctioning bodies and mandatory opponents are involved in a championship fights. There have also been times when a matchmaker has to give justifications to the state athletic commission to approve fights. Most of the time however the issues Bosecker runs into are with managers and family members of fighters. “Look my job is to ensure the functionality of the card runs smooth and that I can entertain fans to keep them coming back” Said Bosecker. Who went on to say “When I matchmake, I already have the fights maid in my head, I put it on paper, and I can guarantee that stylistically it’s going to be a great fight but a favorable fight for the company I’m working for to insure their fighter gets the challenge they need to use as a measuring stick. The issue is, and I’m seeing it more often than not, is that some people aren’t the sharpest tool in the shed and want their fighter to take the easy way. Personally, I love working with people I’ve worked with in the past. It’s the new people in the sport, not all but some, that want to pad records. The problem with that is these kids end up with a 10-0 / 15-0 record and then the get knocked out or really beat up and as a manager you’ve lost three or four years for nothing and if you’re doing that as a manager or promoter you’re doing that fighter an injustice”

Matchmaker Charles Bosecker talks the ends and outs of the fight game with “Stacks” Saldaña and Sean Fitzgerald Photo by Cynthia Saldaña

Charles Bosecker in the ring with Nate Weston and his team at the OC Fight Club

When we watch a fight on TV, us as fans are viewing a finished product. A product that most people have no idea the kind of headaches that have gone into putting on that show. Being a matchmaker is a very difficult job with so many fine points including turning a prospect into a contender and eventually a champion all while keeping fans entertained. Although this writer felt it was one of the easiest jobs in boxing, my conversation with Bosecker changed my outlook, and quickly cleared my head of that notion. Bosecker isn’t signing autographs or headlining the front of the sports page, but without people like him in the sport, the “Sweet Science” wouldn’t be what it is today. When I spoke to  Tom Loeffler from 360 Promotions about the importance of a matchmaker Tom stated “From a promotion side without a good and strong matchmaker the shows wouldn’t be what they are today. It’s not an easy formula to follow to have a balance of fighters that are entertaining but still sell tickets at the same time. Our philosophy at 360 is not to overmatch our fighters but to develop them, and at the same time we don’t want a 20-0 fighter that gets overwhelmed when he steps up to a world class level.” Although it may sound a little cliché Charles “Chuck” Bosecker  is definitely one of the hardest and most dedicated matchmakers in the business. “At the end of the day I just  want to leave behind a legacy for my children and a great impression that can never be erased in the boxing world, something I can look back on when talking with my grandchildren and know that I did that. Eventually I’ll pass the torch to my son and he’ll keep the Bosecker name alive in the sport”

A smiling Bosecker after a great interview with Just Boxing Photo by Cynthia Saldaña

Tom Loeffler states: From a promotion side without a good and strong matchmaker the show wouldn’t be what they are today. It’s not an easy formula to follow.

Photo courtesy of Getty



Anthony Saldana