Webb won the mile at the 2004 Prefontaine Classic, punished the competition at the Olympic trials, and arrived at the Athens Olympics ranked among the top 25 in the world. But after getting jostled and kicked in the shins in the preliminary heat, he finished ninth and failed to advance to the finals.

It's a pattern that has continued for him. Webb excels at middle-distance racing on the pro circuit, where he's running to beat a time and chasing designated pacemakers, called rabbits. But he has a tendency to falter at high-stakes international meets, like the World Championships and the Olympics—races in which strategy, in addition to speed and endurance, is required to win. At the 2005 World Championships, in Helsinki, Webb surged early in the 1,500-meter final; with 800 meters to go, he couldn't sustain the sprint and he finished ninth. At the 2007 World Championships, in Osaka, he overcorrected. He hung back too far in the semifinals, was out of position when the leaders made their move, and then had to run like hell just to advance to the finals—where, depleted, he took eighth.

"If there's one glitch to Webb's racing, it's his tactics," says Steve Scott, who now coaches track at Cal State San Marcos. "He takes the lead very early on, instead of sitting back. He's got awesome speed and strength, but he doesn't have enough faith in his kick. Until it's proven that he can't beat someone down the homestretch, he should utilize that."

The decision to leave Michigan after only a year may have hurt Webb too, because runners learn a lot in the rough-and-tumble world of college racing. "When I came out of high school, I was probably physically prepared to go to the professional ranks, but mentally I wasn't," says Kevin Sullivan. "I think there's definitely value to be gained from learning how to race championship-style races, and there's more opportunity for that in the NCAA."

But as Webb and Raczko see it, Webb is right on schedule, running fast enough to put himself in range of an Olympic medal this summer. "You just have to be patient," Raczko says. "We've realized that you have to build the right way if you want to be the best. At the speeds Alan's running, those seconds don't come easy."

They shrug off any criticism about racing savvy. "If you're strong enough and have done the work, you have nothing to worry about," Webb argues. "You just have to go out and do it. If I had to sum up my mental strategy, that's it: When you've put in the training, you're more at ease mentally, and you can run better tactically."

Yet so far in 2008, his results have been disappointing. Webb finished 16th at the U.S. Men's 8K National Championship, in New York, in March, blaming his poor performance on food poisoning. In early April, at California's Carlsbad 5000, he staggered off the course after two and a half miles, unable to finish. Then, less than three weeks later, he withdrew from Iowa's prestigious Drake Relays, announcing that he wasn't well enough prepared to compete.

"I might have pushed too hard," he says, referring to a jacked-up spring training regimen that had him running about 80 miles each week, hard. "Obviously, I'll get all the benefit of that at some point, but in the short term it was a bit too much." He's reduced his training distance and intensity slightly, and insists that he's not worried; he's just staying focused on Beijing. "I'd rather not race now and be able to race in the U.S. Team Trials."

Meanwhile, as Webb chips slowly away at his times, American runners are gunning to catch up. At the front of the pack is Bernard Lagat, the 33-year-old Kenyan who moved to the States in 1996 and was sworn in as a naturalized citizen in 2004. Last September, just a few days after he became eligible to run for Team USA, Lagat won the 1,500 meters at the world championships. His was the first American gold medal at the worlds since 1908, and it was a brutal wake-up call for Webb, who'll vie with Lagat as well as standouts such as Chris Lukezic and Leonel Manzano for three Olympic berths on July 3.

To make it to China, Webb needs to outrun seven years of hype, put the letdowns of Athens and Osaka behind him, and run the smartest race of his career—without a doubt, the toughest challenge of all. "He needs to be able to relax and let his natural ability carry him, and not overthink it," says David Monti, editor and publisher of the online tracking service Race Results Weekly. "In the last 50 meters, Alan's almost impossible to beat. But the question is, Can he get there?"

"More so than his highs, Webb's lows seem to get magnified so much because he's the face of the American mile," says Sullivan. "He's had the transfer year, the injury year, illness years, and disappointment in the Olympics and world championships, but each time he's come back stronger, with more resolve."

Indeed, Webb is relaxed and good-humored, even after this year's shaky start. "I'm confident that if I take care of business and run hard, I shouldn't have a problem making the team," he says. He trails off for a moment, as though mentally scrolling through the ups and downs of the past few years. ". . . And hopefully get back to the finals, and get some hardware this time."

If he doesn't, there's always Plan B. At Webb's pace of improvement—about a second per season—he'll need another four years to challenge the world mile record of 3:43.13, set by Morocco's Hicham El Guerrouj in 1999. "That puts me at 28 or 29—some would say a peak age," he points out. "I hope I don't have to wait that long, but I'm willing to. I've just had the best year of my career, and I love what I do. Time is on my side."