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Chuvalo's 1965 bout with ex-world champion Floyd Patterson was one of the year's best action fights. George never stopped coming forward as he landed clubbing rights to Floyd's head and terrific lefts to his body. Still Floyd showed a heart that everyone doubted he had. He absorbed Chuvalo's fury and used his outstanding hand speed to win a popular decision over George. Although George lost, his courage impressed the crowd. Despite the losing effort Chuvalo was matched with World Boxing Association titleholder Ernie Terrell. When Ali met Sonny Liston in their rematch the W.B.A. stripped Ali and recognized the winner of a Terrell-Eddie Machen bout. Terrell captured a boring verdict and the "vacant" crown. Against Chuvalo, the 6'7" Terrell used a long jab-and-grab, clutching style to outscore George over fifteen rounds.
The roller coaster career of Chuvalo continued into 1966. George traveled to London and was upset by Argentina's Eduardo Corletti in ten rounds. The loss appeared to have pushed George out of the title picture. Instead he benefited by being in the right place at the right time. When a proposed Ali-Terrell fight fell through, Ali agreed to come to Toronto and defend against George. Although the bout was entertaining it was also one sided. Try as he might, George was unable to reach the fleet-footed Ali. For all his efforts, Chuvalo received numerous jabs, hooks, uppercuts and crosses from a prime Ali. Even in losing, George received the respect of the public for his gaminess. Later in the year Chuvalo met fellow brawler Oscar Bonevena of Argentina. What looked to be a great match up between the two sluggers turned out to be a dud. Oscar "finessed" George to win a ten round decision.
George got back on track in 1967. Two kayo victories over Willi Besmanoff led to Chuvalo being matched with the streaking Joe Frazier. "Smokin" Joe had won the 1964 Olympic Gold Medal and was undefeated as a pro. George was to be his toughest match to date. Frazier was at his best in this battle as he ravaged George throughout with his famous left hook. To his credit George gamely refused to fall but the referee saved him in round four. Again just as it appeared that George's tenure as a top contender was over Chuvalo got one more chance. An impressive upset kayo win over highly regarded Mexican Manuel Ramos put him back in the rankings. His success was short lived. In 1969 he met huge Buster Mathis. Buster's only loss had been to Frazier and he needed to win to set up a rematch with Joe or a shot at the W.B.A. titleholder Jimmy Ellis. Mathis who was a fine boxer for a big man gave George a boxing lesson over twelve rounds. George closed out 1969 in a "White Hope" battle versus popular but erratic Jerry Quarry. For six rounds the Irishman outboxed Chuvalo who was cut and bleeding. Jerry looked to be on his way to a comfortable point win or even a TKO. In round seven George went for broke and clubbed Jerry to the canvas. Quarry was listening to the referee's count on one knee but at "10" he failed to rise. Jerry quickly jumped up and claimed he had lost track of the count but his protesting fell on deaf ears and Chuvalo's kayo victory had him back in the top ten.
The win over Quarry landed George another bout with an Olympic hero. George Foreman had won the Gold Medal in 1968 and he was climbing quickly up the professional ladder. A win over Chuvalo would look nice on his record. The bigger, stronger Foreman was in control from the start. He pummeled Chuvalo at will and in the third round he sent Chuvalo reeling across the ring. Only the ropes prevented a knockdown. Still Chuvalo kept his feet but was defenseless against Foreman's follow up barrage and the referee stepped in. In 1971 Chuvalo dropped a ten round duke to ex-champion Jimmy Ellis. George did manage a points win over still dangerous ex-contender Cleveland Williams. In 1972 Chuvalo got yet another opportunity as he again faced Muhammad Ali. Ali had lost to Frazier in 1971's "Battle of the Century" and now he was taking on all comers while awaiting a rematch with Joe. Although George gave a respectable showing the great Ali again outclassed him.
From this point on George slowly faded from the picture. He hung around a few more years dominating the Canadian heavyweight scene but his days as a world class contender were over. Still after absorbing the punches of Ali, Frazier, Foreman, Quarry, Patterson and Ellis he stood tall with his feet planted firmly on the ground. He wouldn't have it any other way.