September 2026

FIGHT OF FANTASY: FELIX TRINIDAD VS. JARON ENNIS By Anson Wainwright

left hook would have been the key punch to land on Boots. Because Zayas – who doesn’t have nowhere near the power of Trinidad, nowhere near the accuracy of Trinidad – was barely missing those punches and Boots wasn’t seeing them, especially when Boots was in the southpaw stance. “That left hook – respect to Joe Frazier – was one of the greatest left hooks. And once it touched you, you were never the same. And Trinidad was an incredible finisher. So if Xander was able to rock and hurt Boots, what do you think Trinidad would have done? You give Trinidad that minute, he’ll finish you. He won’t let you survive. He’s like Sugar Ray Leonard – he had that gene; when he saw you hurt, you’re not going to survive. Trinidad was the same. “It would be similar to the Zayas fight, but we’re dealing with Tito Trinidad, one of the greatest punchers ever, and Boots is not there yet. I could see Trinidad rocked, hurt and dropped. He’s been dropped half a dozen times, but he gets up and gets meaner and knocks you out. Yes, his chin was a little suspect. His power wasn’t. “It would be an explosive, short fight. Boots is not going to change his ways, and Bozy [Ennis, his father and trainer] demands that of him. So, he’s not going to change for Trinidad. I think he gets hurt and the Philly comes out of him, it turns into a war and Trinidad

a prime Trinidad were to land those same punches,

I doubt Ennis would survive. Remember,

Trinidad was one of the most vicious punchers of his generation. The last thing you want to do is go toe-to-toe with Tito. “So, for me, the Ennis- Trinidad matchup would come down to this: If Ennis were to fight more responsibly than he did against Zayas – somehow resisting his instinct to brawl – he would beat Trinidad fairly easily, possibly even knock him out (although Trinidad also had a good chin). “If Ennis were to stay true to his thrill- seeking nature, he would have a difficult time staying on his feet and remaining conscious. “My prediction? Ennis and his handlers aren’t stupid. They would be well aware of Trinidad’s ability to hurt his opponents and fight accordingly. Although, as we all know, the best laid plans often go by the wayside in the heat of battle. “I think Ennis would keep his cool, outbox Trinidad and win a clear decision.” Prediction: Ennis PTS

Michael Rosenthal Former Ring Magazine editor-in-chief “I think this would be a bad matchup for Ennis – at least the version of Ennis who stopped Xander Zayas in seven rounds in June. “Ennis would be the better boxer and more gifted athlete. He would be capable of outboxing Trinidad much the way the clever Winky Wright and Bernard Hopkins did in one-sided bouts in the 2000s. “Here’s the problem for Ennis: He’s not a methodical technician, as Wright and Hopkins were. Ennis’ nature is to fight, which is one reason he encountered brief but alarming trouble against Zayas in the third round of their fight. “Zayas seemed to hurt him with multiple right hands in that frame, which raised eyebrows. If

Joel Diaz World-class trainer

“A fight between Tito Trinidad and Boots Ennis would be a good fight. It would have been an attractive fight. Styles make fights. “I think Boots Ennis is well-skilled, fast hands, but I saw his fight versus Xander Zayas. Xander was landing some good shots on him. Xander does not have the power Trinidad has. Trinidad was a fighter with a lot of patience, walking you down, aggressive, never took no for an answer. “I know it would be a tough fight. I think Boots Ennis would win half of the fight, maybe more rounds. But towards the end, Trinidad’s consistency, aggressiveness and power would slow down Ennis. “Ennis stands and exchanges and throws punches but also gets hit, but Tito Trinidad was a different breed. “Trinidad will get stronger

F elix Trinidad and Jaron Ennis were both elite welterweights before outgrowing the division and making a big impact up at junior middleweight. The two fan-favorites are both known for engaging, action-forward styles that get fans on their feet. Trinidad possessed devastating power, notably with his left hand, and had a fighting spirit that marked him as one of Puerto Rico’s finest. Ennis is blessed with athleticism, power and speed and is the latest in a long line of superlative fighters from Philadelphia. Trinidad burst onto the scene by claiming the IBF welterweight as a fresh-faced 20-year- old, stopping Maurice Blocker (KO 2). “Tito” went from strength to strength, notching 15 defenses over the next six years and eight months. During that time, he bested Hector Camacho (UD 12), Yori Boy Campas (TKO 4), Oba Carr (TKO 8), Pernell Whitaker (UD 12) and Oscar De La Hoya (MD 12, adding the WBC title). The Puerto Rican star enjoyed further success at junior middleweight, where he beat U.S. Olympians David Reid (UD 12) and Fernando Vargas (TKO 12). Tito became a three-weight world titleholder when he claimed the WBA middleweight belt by bludgeoning William

Joppy (TKO 5), then came unstuck against Bernard Hopkins (TKO 12) for the undisputed middleweight championship. He fought on but never recaptured former glories. Ennis, who recently entered The Ring’s pound-for-pound ratings at No. 9 and is No. 1 at junior middleweight, learned to box from a very young age with his father and brothers in Philadelphia. The 29-year-old brutally dispatched the usually durable Sergey Lipinets (KO 6), Thomas Dulorme (KO 1) and Custio Clayton (KO 2) on the way up. He then enjoyed a homecoming against David Avanesyan (TKO 5) to cement himself as IBF titleholder. In his third defense, Ennis became a unified titleholder, adding the vacant Ring championship and Eimantas Stanionis’ WBA belt with a six-round thrashing. The American switch-hitter moved up to junior middleweight and in his second outing dazzled while collecting Xander Zayas’ WBA and WBO titles in seven rounds. Both Ennis and Trinidad are used to being the bigger man but would be of similar size to each other. Trinidad stands 5-foot-11 with a 72-inch reach, while Ennis is 5-foot-10 and has a 74-inch reach. Had their respective careers aligned, it would have been a fantastic matchup.

Sergio Mora Former junior middleweight titleholder/ commentator “I think it would be an excellent mythical matchup. Especially Boots coming off this star- making performance that everybody is talking about. It crossed over. “Trinidad had good feet for a hard puncher that needed to dig down. He was never on the heel of his feet; he was on his toes. He was always in that sprinter stance. That’s what made him have faster feet to close the distance. “I think Trinidad is an all-time great, and that

in the later rounds, and I think he would have stopped Ennis.” Prediction: Trinidad TKO

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Questions and/or comments can be sent to Anson at elraincoat@live. co.uk and you can follow him on X @AnsonWainwr1ght

catches him. Trinidad would have beat Boots and stopped him.” Prediction: Trinidad TKO

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