Esteban de Jesus was among Puerto Rico's best fighters in the 70s and the first man to beat Roberto Duran on points, scoring an early knockdown in their first fight fought above the lightweight limit. He would lose two subsequent title fights to Duran by TKO, first in a failed try to wrest Duran's WBA lightweight crown in 1974 and the second in a title unification bout in 1978 after he had won the WBC title by stopping Japan's Guts Isimatsu earlier . De Jesus would also vie for the junior welterweight title losing on points to Colombia's legendary Antonio Cervantes in 1975 and to ageless American wonder Saoul Mamby by 13thr ound TKO in 1980 which proved to be his farewell fight. De Jesus however also held quality wins over Edwin Viruet, Pablo Baez, Alfonso "Peppermint" Frazier, Buzzsaw Yamabe, Rudy Barro, Ray Lampkin, Raul Montoyo, Hector Medina, Vicente Mijares and Chu Chu Hernandez, all world class campaigners in his days. He finished with a total log of 58 wins, 33 by KO, against only 5 losses, his other defeat coming on points decision early in his career from Venezuela's then world featherweight champion Antonio Gomez in 1971.

Roger Mayweather on the other hand was the original Latin assasin having beaten a number of top boxers mostly from Mexico and Puerto Rico as Adrian Arreola, Arturo Leon, Robert Munoz, Sammy Serrano, Benedicto Villablanca, Jorge Alvarado, Mario Martinez, Kiko Bejines, Sergio Zambrano, Sammy Fuentes, Rene Arredondo, Mauricio Aceves, Rodolfo Gato Gonzales, Vinny Pazienza and Jose Rivera in establishing lengthy reigns as junior lightweight and the junior welterweight. He would have his waterloo however in the person of Julio Cesar Chavez who beat him by TKO in title fights at 130 and 140 lbs. He also suffered losses to Tony Baltazar, Rocky Lockridge ( 1st round KO), Freddie Pendleton ( KO 6), Pernell Whitaker (UD) in his prime and to Rafael Pineda, Fidel Avendano Ray Lovato , Zack Pineda and Kostya Tzsyu later in his career.

Given these respective credentials, I am leaning towards a De Jesus victory either by UD 15 or late round KO/TKO. Both were hard hitters but I think De Jesus had the stronger chin and longer stamina. De Jesus was also a strong, fast starter and given how Lockridge and Chavez in their first fight blitzed Roger, an early KO win for the big punching Esteban is also not a remote possibility.

Hello Zebbie! First off, a great answer from my friend Toughguy and I completely agree. Roger Mayweather had a great resume, fighting great fighters such as Pernell Whitaker and Julio Cesar Chavez. But, as good and skilled Roger Mayweather was, he isn't Floyd Mayweather Jr., and Roger can be hit very easier than Floyd. Estaban DeJesus was the first man to defeat the great Lightweight Roberto Duran, and that is one hell of an accomplishment to beat Duran in his prime. I agree with Toughguy that DeJesus should be a Hall of Famer, because beating Duran alone is a great accomplishment. However, back to the matchup, Mayweather has been knocked out and stopped before, and DeJesus will catch him on the chin late in the fight. In the early rounds, Mayweather will box. But in about round 10, DeJesus begins to land many punches, forcing the referee to call a stop to the fight.

DeJesus TKO10.

Great match Z please keep it posted a while longer. Thanks my friend. Roger Mayweather was certainly a talented and strong fighter and he did have some quality wins in his career but in Esteban DeJesus we have a man that I believe should be in the Hall of Fame He won some titles and was the first and only man to defeat Roberto Duran as a lightweight which was a tremendous upset of course and he floored him several times in their fights as well. He was a boxer/puncher and a very skilled ring tactician. In a fight between these two men there would be some good action filled moments and seings in momentum but in the end Dejesus would prevail.

Dejesus W15 UD

Nothing I could add to tough guy's answer. Good answer.