This question depends on how you are defining "fighter". Roy was the most naturally gifted of the three, and would be my favorite in head to head match ups (understanding that this is boxing and all three could bang, so anything can happen). Benn was the meanest, best defined "fighter" of the trio (vice "boxer"). Eubank was, in my opinion, the most cerebral and awkward of the three, with arguably the biggest punch (all three were beasts in my opinion, but the shot Eubank landed on Watson was scary).
When looking at level of competition, I feel like Roy takes it with wins over Hop, Ruiz, Tarver, and Toney. Benn has G-Man and Barkley on his resume, while Eubank has Watson and Benn. Looking st the style match ups, Roy's natural gifts/speed are a nightmare for both, while Eubank probably gives Roy the harder fight than Benn.
Now for the controversial part of my post: I think Roy ducked both fighters and I started to lose respect for him for not fighting Benn after Nigel beat G-Man (Roy's friend). This was the period where Roy started to look at boxing as purely business and risk vs reward, and stopped chasing greatness. Seeing Gerald crippled definitely had an affect on Roy, and while I don't blame him for looking out for his and his family's best interests, I have to be honest and say it affects his historical rankings on many lists. The most frustrating aspect of this is that I'm pretty sure he could've run through Benn, Eubank, Darius, Collins, Frankie Liles (Collins/Liles would've been toughest style match ups of that group, but I still think Roy wins)...etc., and would've retired as one of the top two or three p4p ATGs EVER. Instead, we have to watch the most talented boxer ever lose to people who shouldn't even be his sparring partners. Sad.


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