Boxing is the original Rainbow Coalition. Men and women, blacks and whites, Hispanics and Asians, Christians, Muslims and Jews found a home sweet home in the sweet science. Everyone from stone cold killers to Harvard grads has been seduced by the manly art.

The matchmaker Chris Middendorf is one such person. He does the matchmaking for Gary Shaw, Laila Ali, Scott Wagner, Ballroom Boxing, Tommy Gallagher in New York, P.J. Augustine in Philly, Raging Promotions and District Sport in DC.

Middendorf was born in Norfolk, Virginia in 1952 and raised on Long Island and one of his first great loves was the water. “I grew up on Long Island and I sailed all the time,” says Middendorf. “That’s what I did as a competitive sport and was a collegiate All-American at Harvard and was the captain of the Harvard sailing team.”

In addition to sailing at Harvard, Middendorf studied art history. “Theory and criticism,” he says. “It was really about how art movements developed. I also took film history and criticism as a minor. I was more interested in how the social, economic and religious changes of the time affected the art. I don’t believe art – or boxing – operates in a vacuum. Other things interact with it and cause it to change.”

After graduating from Harvard, Middendorf went into the art business in Washington, D.C. One of his bestsellers was a print of a picture called “Stag at Sharkey’s, a 1917 lithograph modeled on the 1909 painting of the same name by the American artist named George Bellows. “Stag at Sharkey’s” is one of the great boxing images in art history. Middendorf says “It was just always one of my favorites.”

I ask if Middendorf sees any connections, “Stag at Sharkey’s” aside, between art and boxing.

Middendorf laughs and says “Artists and fighters are very similar. They’re only as good as their last fight or their last show. For the most part they work alone. They train alone. A fighter may spar with someone, but for the most part he’s working out by himself. He’s running by himself. He’s hitting the speed bag by himself. They tend to listen to a lot of people and get upset that they’re not getting paid enough or their manager or dealer is not keeping them active enough or somebody else is getting paid more than they are. Or somebody else is moving up through the system, getting more visibility than they are. Once they’re successful, they still can be very insecure. Those are the main similarities.”

Eighteen years ago Middendorf became an investor in a light heavyweight named Prince Charles Williams who was number nine in the world at the time. It was a good investment. Four months later he beat Bobby Czyz and won the crown. He had Prince Charles Williams for three years. He was a manager for five or six years. Then he switched to matchmaking.

Middendorf is old school at heart, but digital at his fingertips, and he swears by the internet when it comes to matchmaking. “We’re coming to a point where in the morning I’ll go on the internet and I’ll read a story and I’ll click on The Sweet Science to read some press links and I’ll be able to read about a fight card in Manila where there was a very exciting 6-round fight. I’ll be able to go and click on that and get streaming video at 8:15 in the morning in Washington, D.C. and watch that fight. I think everybody’s ability to do that is going to change the whole way the marketplace is. I think the market is going to become more worldwide and that has to do with the internet. So I’m interested in that type of thing and how it develops.”

Boxing is filled with people who feed off boxing yet insist on disparaging its future. I can’t tell if they’re doomsayers, kooks or drama queens.

Middendorf is none of the above. “Boxing at its best is as peak a sports moment as you can get,” he says. “I mean the last minute of a Final Four championship game is right up there. Overtime in a Stanley Cup playoff game is right up there. I love the moment when a home run wins a World Series game as well. But boxing is really right up there. We’re a nation of sports fans, and when the sport is good and the sport is strong – and I think boxing is as strong as it’s been in a while – and I think it’s going to continue – we’re just going to gain more fans. So I’m definitely not a doomsayer.”

I ask the matchmaker who is not a doomsayer if it seemed the least bit strange that a Harvard alumnus was entrenched in boxing.

Middendorf pauses. “What I do, and what I’ve always done my whole life, is make deals, whether I was negotiating with the people in my neighborhood when I was cutting my lawns as a 10-year-old or what I do now. So I’m always making deals,” he says. “I find it humorous when I keep seeing those articles on the internet by prominent people who’ve come up with a new formula for saving the sport. My whole thing about trying to save the sport is to make sure each deal which gets made is the right deal and a fair deal.”

I wonder if he can elaborate.

“If I’m calling up a 4-round fight, finding an opponent to fight a prospect, I’m treating the human being in that transaction in a way that they’re feeling as if they’re being treated fairly. They’re being paid fairly. They’re being protected. They’re going to get their medicals paid by the promoter. They’re going to come in and have an experience where they’re gonna feel there’s a level playing field. And win, lose or draw,” Middendorf says, “I’ll be able to pick up the phone and call them the next day and ask them if they want to take another fight.”

That does not sound like the way things are traditionally done in the sport of sports, which is all the more reason to turn it around.

“You go to Philadelphia and Philadelphia is a shell shocked town in terms of the gyms and the younger fighters and people they turn to for information, the older fighters, the older trainers and managers who have been through that time when everybody was completely used and abused. I mean Philadelphia is a very difficult city for that reason,” says Middendorf. “Those guys can’t make the sort of money they made way back then. Combined with the fact that television is not allowing them to get away with what they got away with before. And television is demanding a better and better product, and that trickles down, so the promoter putting on the show has to put on better fights. The audience gets used to seeing better fights on television and therefore wants better fights in the club show and the promoter is forced to put on better fights in the club shows. In order to do that, you’ve got to be treating people fairly. On the grassroots level, that’s the way the sport is changing and that’s where it’s getting more and more healthy.”

I ask for a specific example of how boxing is getting healthier.

“Last month I put on Andre Dirrell, the Olympic bronze medalist. He’s made a choice right now not to sign with a big promoter. But part of the problem is matching him up. We had some ups and downs and somebody got bumped off the card at the weigh-in, but I replaced him with a guy 3 and 4. Everybody around him told him, ‘You can’t go in and fight the bronze medalist,’ you know, ‘You’ll get killed.’ But he got treated right. He got paid right. He fought a great fight. If the referee hadn’t stopped the fight it would have gone the distance. I told him that I was going to bring him back on the next card there because he fought so well. Anyway, he called up before the fight and he wanted his four family members to get tickets. We were happy he took the fight. We wanted his family there to support him. He could have easily gone away feeling like he was used and abused and stopped by a bronze medalist and that we had no interest in him. But I think the opposite is the case. He’s gonna come back and I’ve got a 3 and 5 guy I want to match him up with, which will be a fair fight for him, and he’s not going to leave the sport bitter.”

In my neighborhood, we call that a fair shake. But boxing’s underbelly resists change.

“The industry is under pressure to change,” Middendorf says. “It’s under pressure from fear of legislation from Capitol Hill. It’s under pressure from television to deliver good fights. It’s under pressure from fans to serve them up good fights. It’s under pressure from managers and fighters wanting to be treated fairly. And because of the internet, everybody’s got all the information. They can read about abuses by certain promoters or good things that are happening to certain people. The information is there from the top to the bottom. For the most part, you can find out how much a big fight is paying and you can deal with that in a way where I can say to a fighter, ‘Look, this is what’s available for that big fight,’ and they can go, ‘Oh, gee, I think I should be getting more,’ but it’s easy enough to reference them to certain articles where they can see that they’re getting the right amount of money, they’re being treated fairly, nobody is talking advantage of them.”

According to Middendorf, it’s out with the old and in with the new.

“It is actually similar to the end of the studio system in Hollywood,” he says. “It’s been great working with Gary Shaw, because he does not demand that fighters sign options to be on his shows, which is very unusual. We are giving people opportunities that they would normally not get. Now a young fighter and his manager can come fight a few fights on some Ballroom cards, and in their hometowns, then graduate to a fight here and there on ShoBox. And if they really perform well and we do what we do well as a team, they can potentially become stars. By not forcing indentured servitude we leave ourselves open to them jumping ship, but I maintain that disloyal people are going to be disloyal people whether we have them under contract or not. But by being open and straight, we can be great promoters and put on terrific shows that make TV and fans like our shows, which begets more TV and more shows, and we can be the sort of promoters that a big star will want to hire to do his show, because he knows that he will be treated well and that we will watch his money like our own. I know there are times where you think it may be foolhardy, but I think that we will win far more than we will lose with this limited free agent format. A great fighter will be drawn to us from the beginning, the middle or the end of his career, because he will know we will do a very good job of representing him. And if we do he stays and if we don't he leaves. Nine times out of ten we will do the job and he will stay.”