After the 1996 Olympics there was much speculation as to whether Dolan would retire. Dolan considered the option, however, his competitive spirit was still eager for more victories. Dolan continued to compete in and win at the United States swimming championships. In 1998 he became the first male swimmer since Johnny Weiss-muller in the 1920s to win four events at two United States National Championships. Dolan underwent knee surgery in 1999, but he returned to the pool to prepare for the Olympics again.
Dolan had to fight off a lung virus that had him breathing from an oxygen tank only a week before the Olympics in Australia. He not only managed to repeat his gold medal win in the 400-meter individual medley, but he also broke his own world record in the event. He completed the race in four minutes and 11.76 seconds, a half-second faster than his previous Olympic run.
After the 2000 Olympics Dolan traveled the country as a motivational speaker and spokesperson for the American Lung Association. He still swims at special events. In 2001 he organized a relay swim to raise money for the facilities of the victims of the September 11, 2001 terrorist attacks on the Pentagon and the World Trade Center. He also participated in the 2001 Holiday Invitational swim meet at George Mason University.
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