Mega-fights are very rarely easy to put together. Every major pay-per-view has the lingering stench of financial squabbles. Critics will say this is the downfall of boxing, but it has always been this way. Just look at Sugar Ray Robinson vs. Archie Moore.

No, these two all-time greats never squared off in the ring, but in 1959 they came very close to doing so. Both Sugar Ray and the “Old Mongoose” met to discuss what could have been a career-defining fight. However, in the end, the bout fell victim to boxing’s surest deal-breaker: money.

The opportunity for both men came when they were way past their prime, but at the height of their popularity. Robinson had just regained the world middleweight title for the fifth time with a defeat of Carmen Basilio. Moore was coming off his victory over a much younger Yvon Durelle. It was a fight in which he came off the canvas four times to win.

Robinson’s victory over Basilio in March of 1958 avenged an earlier loss and yielded one of the biggest paydays of his career. A rubber match between the two seemed inevitable, but it was not to be. Robinson was not happy with the money being offered nor was he pleased with the politics of the National Boxing Association (NBA). Instead of signing to defend his title, he held out for better terms.

The NBA did not blink and on May 4, 1959, stripped Robinson of its middleweight title. He was still recognized as the world middleweight champion, but by this point, his eyes were on Moore’s light heavyweight crown.

“He (Moore) was hot property,” said Robinson. “At this age, and with his quips and his goatee, he sold tickets.”

Sugar Ray began to see the dollar signs when Matty Fox, the owner of the pay-TV company, Skiatron, came to meet with him in New York in the middle of 1959. Skiatron was one of the pioneer companies in pay-per-view television. In 1953, it tested an over-the-air system called, “Subscriber-Vision,” which used punch cards for billing and descrambling in household televisions.

For the proposed Moore vs. Robinson match, Fox wanted to go a step further. On his yacht, he told Sugar Ray of a plan to install coin-slots on home television sets. Skiatron would then charge each household a dollar to view the fight.

“And to get it started,” said Fox, “I’ll guarantee you (Robinson) and Moore a million dollars to split between you.”

The fight would have been a classic matchup between boxing’s grand old men. Robinson was 38 at the time. Moore was 45. With Fox’s plan in place, the fight would have yielded millions.

There was a bit of hesitation from Robinson’s handlers. Fox may have flashed a great deal of cash in Sugar Ray’s face, but his assets were minimal. Also, there were a handful of other promoters who could definitely make the fight happen and bring in a nice paydays. With Fox, there was great deal of uncertainty.

But for Sugar Ray, half a million dollars was all he needed to hear. He was never very good with managing money. He had retired in 1952 but was forced to return to the ring in 1955 because he was broke. By May of 1959, he had been out of the ring for more than a year. Robinson needed a fight, but more importantly, he needed a payday.

Robinson decided to discuss the fight with Moore himself. He invited the Old Mongoose and his wife Joan to dinner at his home in Manhattan. After dining on a New Orleans shrimp á la Creole dinner prepared by Robinson’s then-wife, Edna Mae, the two fighters went into another room.

When they were alone, Robinson laid out the plan. The two would receive a half a million each from Skiatron. Moore was very interested but tentative.

“This was something I had wanted to do for quite some time, but I played it cool,” he said. “I knew what was in the air, and I knew just what I wanted.”

Sugar Ray expected Moore to jump at the opportunity to make $500,000. However, Moore had long-term plans in mind.

“Why don’t we each take $250,000 and the rest in stock in Skiatron?” asked Moore.

Not only would this have paid dividends in the future, it would also have allowed the two to save a boatload in taxes.

“That’s not the deal he offered,” said Robinson, who according to Moore was becoming agitated. “He offered us a million to split.”

“I understand that,” Moore shot back. “The price is right, Ray. But inasmuch as we can’t walk away with a half-million each, why don’t we work out a deal with those people where we each invest $250,000 of our purse in the theater television? This would set us up economic-wise for life.”

According to Moore, Robinson became belligerent and would not even consider approaching Skiatron with the stock option proposal. Sugar Ray said that he presented the idea of deferred payments as an alternative way to save on taxes.

Regardless, Moore did not feel comfortable with Skiatron’s offer or doing business with Sugar Ray. He said he would consider the proposal, but the next day he flew to Montreal and signed for $250,000 for a rematch with Durelle. This time around, the Old Mongoose polished Durelle off in three.

“Easy money,” said Robinson, “but I’ve never forgiven Archie.”

“This kind of made Ray mad,” said Moore, “but if he would have at least talked to the theater television people about this and given them the proposition, I would have gone for the deal even if they had refused.”

Robinson finally made it back into the ring in December of 1958, knocking out Bob Young in two rounds. A month later, he lost his middleweight title to Paul Pender by a split decision. Although Sugar Ray challenged for the title three more times, he never regained it and retired in 1965.

Moore continued fighting until 1963, packing it in shortly after being knocked out in four rounds by an up-and-coming Muhammad Ali. While he had many fights for good money, he never received another opportunity along the lines of fighting Sugar Ray.

“I have always regretted not having fought Sugar Ray Robinson,” said Moore, “and we would have fought if he had agreed to the terms I felt were quite fair . . . If he had taken my suggestion and the television people had gone for my idea, we both could have been rich men today.”