Leonard was a shell of himself against Kevin Howard. These mythical head to head matchups are meant to be prime for prime unless you state otherwise. So I'll play along. Yes, a prime Davey Moore gives the rusty, coked up "Kevin Howard" version of Ray Leonard a very tough fight. Hell, might even beat him. Prime for prime, Leonard destroys Davey Moore. Davey Moore was a very good offensive fighter with very little defensive ablllity. The jump-up to someone of Leonard's experience and skillset would see Moore dismantled as he was against Duran. Moore's arsenal was fine for Charlie Weir, Gary Guiden, and even Kalule with limited firepower. Leonard would be too much as was Duran.
Leonard was under-motivated for Howard, and rusty for sure. But let's not exaggerate his condition. Leonard kept himself in good shape and had been training hard. Every fighter and celebrity uses "drug use" as an excuse or hook for sympathy. Leonard may have done a bit of partying in his off-time, but he was no crack house/drug addict case.
Sorry to buck the trend of a competitive Davey Moore, but I could see a few inconsequential rounds, maybe 3, before SRL utterly destroys Moore..a devastating ko...Leonard would take his head off with a hook and follow it up with about three free shots as Davey slowly goes down.
Sugar Ray Leonard did the CBS Sports broadcast of the Davey Moore vs. Gary Guiden bout. In his own words, 'Davey Moore's wide-open hard throwing right hand style is very dangerous for anyone' 'Because he's reckless and wild, that makes him a danger for anyone, but he's quick too and can hurt anyone with one-punch'
I think Ray loses, to be honest. If an unknown Kevin Howard can put Leonard on his ass, Moore could Knock him out. Remember, Duran hit harder than Leonard, and Leonard did not have the ability to bang the drum or play dirty like Duran. That's why Duran beat him.
Still say Ray would stop Davey late, but Davey had never been down until Duran, and I don't think Ray would put him down.However, he would use his boxing ability to methodically take Davey apart, but until the stoppage, he would be given hell, and then some.
Leonard would find that Moore would offer stern resistance for a while,but Ray's superior skills would enable him to stop him around the ninth or tenth.
Howard was a small target. Moore's offense is up to the task, his defense is not. Not a walkover by any means, but I'd be comfortable betting on a Leonard UD as the near inevitable outcome. Would not be wide, close-ish but clear. I don't really see him knocking Moore out. Kid could take a punch and was game.