While handling Pacquiao, the Hall of Fame executive finally helped arrange the long-awaited fight between the pair of generational greats, which Mayweather won by unanimous decision in 2015.

Eleven years later, Mayweather, 49, and Pacquiao, 47, are supposed to square off in a sequel. At the moment, it appears the fight is on the ropes, however, after it was originally announced for September 19 at the Sphere in Las Vegas and later moved to September 25 at T-Mobile Arena.

Although a litany of legal issues for Mayweather have complicated the clash on paper, Arum believes the pitting will be in Pacquiao’s favor if they ever enter the ring.

“It's the great unknown, considering their ages,” Arum told The Ring. “But right now, I would favor Pacquiao, because he's been the more active guy and he’s been in the gym and even fought last year. It appears to me he’s in better boxing shape than Mayweather. It certainly will be an entertaining fight, if it happens.” Pacquiao (62-8-3, 39 KOs) returned from a four-year retirement in July of last year and fought to a majority draw against Mario Barrios.

Mayweather (50-0, 27 KOs), meanwhile, announced in February that he was ending a nine-year retirement to fight Pacquiao again amidst ongoing reports that he’s in financial trouble.

“I have no knowledge of how much money Mayweather has, who took his money, whether he still has money, or not. I’m not going to speculate,” Arum said. “But he spent money like I had never seen before. If you told me that it looks like he's run out of money, or is running out of money, I wouldn't be surprised.”

If the on-again, off-again bout between Mayweather and Pacquiao happens, oddsmakers favor Mayweather to win.

DraftKings has installed Mayweather as a -205 betting favorite and Pacquiao as a +160 underdog.