Middleweight – James Toney vs. Julian Jackson
Best time to make this fight: February of 1992
Reasons: IBF king Toney was just two months removed from his scintillating draw against Mike McCallum and on February 8 he fought a non-mandatory in Dave Tiberi, a man he badly underestimated and for whom he struggled mightily to make 160. Jackson was one of the few names “Lights Out” missed during his middleweight tenure and had the powers-that-be made the unification fight with WBC titlist Jackson instead of matching him with Tiberi, one would believe that Toney would whip himself into prime condition.
Meanwhile, Jackson was at his terrifying peak as he starched Herol Graham, Dennis Milton and Ismael Negron, the latter of whom he fought on February 15, 1992 (five months after Milton). Theoretically, there was enough space in each man’s schedule to make this fight.
Why this fight made the list: When he was a young champion Toney hungered for competition even more than he desired junk food. Jackson, in turn, thirsted to prove himself against the very best but often was denied due to the whims of promoter Don King and the disinclination of star opponents to taste his supernatural punching power. Toney-Jackson would pit one of boxing’s premier ring scientists against its most explosive hitter.
What might have happened: Even at 23, Toney’s boxing IQ was among the highest in the sport and most times his chin was sturdy. Reggie Johnson did drop Toney in the second round of their June 1991 encounter, a development that would have emboldened “The Hawk” to swoop in. Jackson’s one-punch KO ability in both hands was legendary and he would have tried to score another against Toney every second of every round. Because Jackson’s power posed such a severe threat, Toney’s defensive radar would’ve been set on super-sensitive. Plus, Jackson’s wider punches would have created plenty of countering opportunities. Toney would capitalize often enough to secure a decision.
Honorable mentions: Gerald McClellan vs. Jorge Castro, Mike McCallum vs. Julian Jackson II