“The Floyd Mayweather vs. Brian Kenny interview was so widely covered in the sports world at the time, that we decided to take advantage of that well-known relationship between the two to create a fun ad for our fans,” said Seth Ader, senior director of sports marketing at ESPN. “The premise of the ‘This is SportsCenter’ campaign is to showcase this fantasy world where athletes, anchors and mascots live and work together in our Bristol, Conn., headquarters, so it made sense to feature them the way we did.”

Kenny remembers the commercial segment fondly.

“Funny thing, I show up and he comes in with his people and Leonard and we shake hands and say hello and everybody is having a good time,” Kenny said. “As part of the thing we explain he needs to hit the bag for a few minutes. Then we get to the part where they take a picture of me and they tape it to the bag. He goes, ‘Oh man. Oh yeah. OK, start rolling the cameras. You better start rolling.’ He couldn’t wait to start popping the bag with my face on it. He was a little too eager. We all had a good laugh.”

https://www.youtube.com/watch?v=kw9XqiBXKgM

It would take some time before the enormity of the interview would sink in with Kenny. “A little after that, I remember interviewing Charles Barkley on SportsCenter. We had never spoken one on one,” he said. “I was thinking, ‘Introduce myself to Charles, I don’t want to presume people knew who I am. Hopefully this goes well. Charles is a great interview.’ We get a mic check.

“‘Charles, it’s Brian Kenny, great to meet you,’” Kenny recalled saying. “He says, ‘Last time I saw you, Floyd Mayweather was getting all up on your ass.’ I thought, ‘This is going to go fine.’ It has become this icebreaker with other athletes, with fans.”

* * *

Despite Kenny’s best interrogation, Mayweather-Pacquiao, five years later, hasn’t happened. Periodically, before each man’s next fight or slightly after, some writers and fans will flurry anew about whether Mayweather-Pacquiao could be on the horizon. The rest of the writers and fans roll their eyes.

Kenny himself expected, at the time of his interview with Mayweather, that it would happen. He had history on his side. There is no fight that would have made the kind of money Mayweather-Pacquiao could have made that didn’t happen eventually.

Top Rank founder Bob Arum said Mayweather turned down a $100 million purse offer to Pacquiao’s $80 million. Promoters are, by their very nature, prone to exaggeration. But Pacquiao definitely turned down a flat $40 million offer from Mayweather in 2012, not including upside from pay-per-view revenues, which by one estimate would’ve been $160 million. The fight would’ve made more money off ticket sales, sponsorship and overseas rights.

The first round of negotiations began in 2009, and concluded, fruitlessly, in 2010. The two sides agreed to every term except one: advanced drug testing sought by Mayweather, who had become skeptical of Pacquiao’s rapid, successful rise in weight.

There were valid arguments on both sides about Mayweather’s request. Mayweather had insisted Pacquiao would be “easy work,” and that his knockouts of De La Hoya and Hatton paled in comparison to his performances against both men because Pacquiao merely was devouring his “leftovers.” Why, then, was drug testing suddenly a dealbreaker? And Pacquiao’s rise paralleled in part Mayweather’s own physical evolution. As a 16-year-old amateur, Mayweather weighed 106 pounds. When Pacquiao turned pro at age 16, he weighed 105 pounds.

Over time, some of the claims by the Mayweather camp about Pacquiao were comical – uncle Roger would assert that Pacquiao was on something called “A-side meth,” which he helpfully explained that Filipino soldiers used to make themselves bulletproof.

Yet Mayweather’s insistence on advanced drug testing would later prove prescient: Numerous fighters who subsequently underwent something akin to the kind of testing he popularized would test positive. Pacquiao’s various excuses for why he didn’t want the drug testing were inconsistent and flimsy; Pacquiao had a fear of needles, his team said, yet he bore numerous tattoos. As the first round of negotiations dragged out, Pacquiao’s side would try to bridge the gap by proposing testing up to a certain date before the fight – but testing experts said such a cutoff date would be insufficient.

A second round of negotiations, later in 2010, would become so convoluted that Mayweather’s side claimed there were no negotiations at all, only for then-HBO sports president Ross Greenburg to release a public statement acknowledging that he had indeed served as an intermediary for both sides. There were never any serious negotiations thereafter.

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