Later Career
O'Brien completed a hat-trick of breaststroke doubles at the 1965 Australian Championships, but in a year with no international competition, he swam much slower times of 1 min 11.1 s and 2 min 38.6 s respectively. He completed a fourth consecutive medley relay win with New South Wales. At the 1966 Australian Championships, his times were again slower, at 1 min 11.8 s and 2 min 41.6 s respectively, more than 4% slower than his personal bests, but it was still enough to retain his titles and qualify for the 1966 British Empire and Commonwealth Games in Kingston, Jamaica. Critics had written him off, because just six weeks before the competition, he was 16 kg overweight. However, he returned to his peak form by the time the team reached Jamaica, where he won both breaststroke events with times of 1 min 8.2 s and 2 min 29.3 s respectively. His winning run in the 4 × 100 m medley relay came to an end when the Australians were disqualified for an illegal changeover.
In 1967, O'Brien skipped the Australian Championships because he had no sponsorship and ran out of money, forcing him to seek full-time work. The Australian Swimming Union persuaded an overweight O'Brien to make a comeback in 1968 on the grounds that Australia did not have a quality breaststroker for the Olympics. Undergoing a crash diet and fitness program, O'Brien lost 12.7 kg in twelve weeks of intense training. O'Brien was unable to reclaim either of his individual Australian titles, but New South Wales again won the medley relay. Nevertheless, he was selected for his second Olympics.
At the 1968 Summer Olympics in Mexico, O'Brien placed second in his heat of the 200 m breaststroke in a time of 2 min 36.8 s, which placed him 13th. He was eliminated, having been 2.9 s slower than the last-placed qualifier for the final. The eventual winner posted a time 0.9 s slower than that of O'Brien four years earlier. O'Brien did better in the newly introduced 100 m event, winning his heat in a time of 1 min 8.9 s to qualify second-fastest for the semifinals. O'Brien scraped into the final after coming second in his semifinal in a time of 1 min 9.0 s. It was the barest of margins; O'Brien was the slowest qualifier and could not be electronically separated from the ninth-fastest semifinalist, with judges being used to decide the placings. O'Brien went on to finish sixth in a time of 1 min 8.6 s.
O'Brien narrowly missed a medal in the 4 × 100 m medley relay. Along with Michael Wenden, Robert Cusack and Karl Byrom, the Australian quartet won their heat and entered the final as the equal fifth fastest qualifier. In the final, O'Brien swam his leg in 1 min 8.6 s, which was only the fifth fastest breaststroke leg. Australia were fourth at the end of each leg, except O'Brien's, when they were third. Australia eventually missed out on the bronze by 0.1 s to the Soviet Union. O'Brien admitted that his training had been insufficient for Olympic standards, noting that "I needed to put on another thousand kilometres in training". O'Brien also rued the absence of Talbot to motivate him to work, and had a further accident at the Olympic Village when his fingers were slammed by a closing window. Under competition regulations, he was not allowed to bind his hand during competition.
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