initially i assumed he could milk this boxing foray for 2 or 3 boxing matches, assuming he lost handily. after the fury fight, i think he could probably milk it for 2 or 3 additional matches. if he wins any of them, he can milk it for longer.
he should rematch fury first, since he’s still the biggest name, and there’s interest in it. then he should fight wilder, whom he may actually be able to beat. after that, he should just take the biggest names he can find in any order. i expect most of the top boxers will decline this fight if he loses 2 in a row to fury and wilder because (a) it’s a risky fight, and (b) the shine of beating the “lineal ufc hw champ” will be long gone. i don’t really expect him to beat anyone (except wilder, maybe), so after a while interest will dry up.
of course if he wins all these fights, then the line gets longer. that would be a game changer.