So you're a fledgling manager and you're given Vitali Klitschko as a prospect. Your goal is to guide him to a title shot and make as much money as you can from him. He turns pro in 1988. So match him up wisely.
His best shot at winning a title during that era would be fighting the likes of Moorer, Foreman, McCall. I can't see Foreman fighting Vitali at that stage in his career so he'd probably have to fight the other two belt holders. There's plenty of top 10 contenders he could beat during that era like Mercer, Morrison, etc. But i'd have a hard time seeing him beat the very best Heavyweights of that era at their absolute peak.
Yeah Vitali would've had a far better resume competing in the 90s. You don't think he could give Tyson, Holyfield or Bowe issues?
I'd have him wear a tattered hooded cape and bring a scythe along for the ring walk. Instead of Dr Ironfist I'd get him to call himself 'Death from Donbas' or the 'The Killer Kossack'. I'd make him make statements about the weak capitalist dogs and how they cannot stand against a "beast from the east." Moreover I'd have him grab the mic from the presenter and go on a long rant about how the hedonist lifestyle in America breeds soft men and an inferior kind of mindset. Also, I know he was pretty well built, but I'd totally ensure that he did a million crunches a day so that he could flex an eight pack to put that era's flabby heavies to shame. I'd have him call out all the top heavies and accuse them of ducking him while feeding him a schedule of a fight a month against his actual roster interspersed with total cans so that his big square mug was always in the limelight knocking somebody out. While the rage built to a frothy peak at these antics I would prepare the bank account to receive millions from him fighting whoever the F he wanted. Also, Vitali was H2H probably the best of his era so this heel strategy, which kind of relies on him winning, would more likely pay off than not.