There are actually two fights where I'd feel comfortable seeing Winky settle some business: - Antonio Margarito made an annoying habit of calling Winky out a while back (along with every other fighter that was too good for him) and is ironically now a low-risk high-reward fighter thanks to his recent exposure and beatings. Tony can't hurt Winky, so as long as there's enough gas in the tank for Wright to fall back on muscle memory he should be able to comfortably outbox Margarito in yet another beating (but less savage than the ones at the hands of Mosley and Pacquiao - more like a Wright-Trinidad or Calzaghe-Lacy beating). - Felix Sturm was another name often paired with Ronald's a few years back. Sturm still has a shiny belt. It would still be a battle of two of the best jabs in the business. If Wright can make 160 it's worth a shot to try and take that belt in Germany. If he gets robbed, well...c'est la vie. He'll just think "Yeah, put it on my tab" and honestly it would be poetic justice for the unnecessary and perverse humiliation of his buddy Ike.
Sturm/Wright is probably still a good fight. Winky probably has enough in the tank to give Sturm hell.
It'd be sad if he does need money after spending such a long time away from the sport, after he'd finally made his name. The loss to Hopkins shouldn't have affected his earning ability because he was way above his prime weight. After years struggling to make money, he retired when he could, and I hope that's not got him into a bad place.
I really doubt the motivation is financial. He seemed to have his affairs in order and wisely hitched his promotional wagon to GBP (while somehow retaining sovereignty and staying CEO of his own company...very slick). With him it's probably the other, sometimes equally sad reality of aging pugilists not knowing when the lights have faded and the glory passed them by.
I really enjoy Winky's style and hope the best for him, though sometimes I felt like he was one of those fighters who would rather lay off the gas and complain about the decision rather than just going for it.