That happened after he went from the University of Iowa to the University of Florida. There, Dwyer found a coach, Gregg Troy, and a competitive environment that turned him from a swimmer who couldn't qualify for the 2009 NCAA meet into the 2010 NCAA men's swimmer of the year and, two years later, an Olympic gold medalist.
Boost from Evans
He got to Florida only because four-time Olympic champion Janet Evans had become a family friend after meeting Conor's father, Patrick, while giving motivational speeches to a company he worked for. Evans would nudge Troy to let Dwyer join an overcrowded summer training group, and the fit was so perfect, he decided to transfer.
"I found out that summer I wasn't pushing myself all the way," Dwyer said. "When I started winning training sets in practice at Florida against guys who were NCAA champions is when my eyes opened, and I realized I could actually do something in this sport."
It wasn't until he left Florida last summer for Baltimore that Dwyer won his first individual medal at a global championship, a silver in the 200 free at the 2013 worlds, while lopping more than a second from his personal bests in the 200 (now 1 minute, 45.32 seconds) and 100 (48.94).
The departure of Ryan Lochte and Peter Vanderkaay from Gainesville, Fla., left Dwyer without the kind of post-collegiate training group that had helped him make the 2012 Olympic team in the 400 free (he finished fifth) and the relay. Early last spring, he contacted Bowman, asking if he could join one of the coach's famously demanding, three-week training camps in Colorado Springs, Colo.
"It got me in the best shape of my life," Dwyer said.
While Dwyer was at the camp, Frenchman Yannick Agnel, the reigning Olympic champion at 200 meters, also had contacted Bowman and came to Colorado Springs. Both liked the situation so much, they decided to move to Baltimore.
Bowman had ended his own post-Olympic coaching retirement to help a couple of other swimmers prepare for the 2013 worlds. Suddenly he had the nucleus of an exceptional training group, and Phelps had been talking to him about a comeback that became official earlier this year.
"I realized I did miss it, and I was pretty good at it," Bowman said of his return.
Phelps lends a hand
He asked Phelps about giving Dwyer a place to stay while he got settled, and the two hit it off well enough that they have maintained the arrangement.
When Dwyer was competing at the 2013 worlds, Phelps would text him pointers about turns and splits. This season, he has been helping Dwyer work on the underwater dolphin kick.
Bowman's focus has been on getting Dwyer to lower his head position and change the timing of his breathing. The results this season have been good: Dwyer was the overall men's winner of the Arena Grand Prix series, which earned him one year's use of an $85,000 BMW Active7 hybrid.
"I know a lot of swimmers who were good from 15 to 18 but are done with the sport now," Dwyer said. "Being so new to the sport at such a late age, I keep having more and more fun and getting better and better."
Good enough that Winnetka had Conor Dwyer Day three weeks after the London Olympics, where 40 relatives had come to cheer him on. Among them was his grandfather Jim Dowdle, the former Tribune Broadcasting chief who died earlier this year.
Jeanne Dowdle Dwyer still teaches young kids how to swim in her parents' pool. Many have gone on to swim for Loyola and New Trier.
One has gone on to become an Olympic gold medalist. His development pleases those around him, including the person who said, "It's good watching him grow up to become one of the top men's swimmers in our country."
Spoken just like a mom.
Except those words about Conor Dwyer came from Michael Phelps.