vs. Ray Robinson...
He gets stopped late-on against Robinson. He'd no doubt be massively up for this fight, & would pull out all the stops. He just doesn't have the same arsenal or tools at his disposal, & is slightly the smaller man, to boot.
Robinson TKO12 Leonard
vs. Floyd Mayweather...
Now, he's the bigger man, & the one with more at his disposal. There'll be no KO, though, & Leonard will be unconvincing in stages --- but, really, he's stylistically difficult & just flat-out too good for the somewhat-unproven 147lb. version of Mayweather.
Leonard UD12 Mayweather
vs. Oscar De La Hoya...
They'd never get past the negotiating table!
If they did, however, a competitive fight for the first five rounds slips out of De La Hoya's reach, as he finds himself more or less unable to deal with Leonard's output & speed. Each man would be rich enough to retire on the purse of this fight alone.
Leonard UD12 De La Hoya
vs. Jake LaMotta
A difficult & dangerous fight for Leonard, who suffers a shock knockdown in the second. He's unable to deal with LaMotta's intense pressure early, & has to rally from the knockdown & a bad cut over the right eye to win a surprisingly close decision, on the order of 115-113. He would've beaten LaMotta a little more convincingly in a return.
Leonard SD12 LaMotta
vs. Shane Mosley...
The Mosley who fought De La Hoya first-time around at Welterweight was an outstanding force --- he overcame a large points deficit early, in the biggest fight of his career, to out-hustle what was then one of the very elite pound-for-pounders. He had size, style, rhythm, speed, & those great combinations --- unfortunately, Leonard has more of most of that, & isn't as hittable as De La Hoya at this weight. Leonard in a
relatively close fight.
Leonard UD12 Mosley
vs. Felix Trinidad...
Stylistically (& realistically), this is the easiest outcome to predict. Leonard could be hurt, but not taken out, by Trinidad's power, & he's not going to drop a decision in a million years. His obvious style advantage & edges in speed, flexibility & ring generalship make for a long night for the Puerto Rican wonderboy. Leonard wins going away, having dropped just two rounds --- & having dropped Trinidad in the second stanza.
Leonard UD12 Trinidad
I have him going 4-1, & I think many people may have that, as well.