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.