Keeper Tim Howard is already 28, and he has not one, but two outstanding predecessors - Kasey Keller and Brad Friedel - to match or exceed.
In his five games at the helm this year, Bradley has prepared and motivated his team sufficiently to beat Denmark, Mexico, Ecuador and China, and tie Guatemala. None of those teams is close to the world's elite, which is what U.S. Soccer presumably aspires to be, and all of the games were friendlies.
Now it gets serious. El Salvador has played in just two World Cups, Guatemala has never attended the big dance. Trinidad & Tobago debuted last year. In the next week they can poke Uncle Sam in the nose by beating or even tying the regional powerhouse and most convenient political target.
The national soccer team - rightly or wrongly - bears the pride of a people when it steps on the field. And every team has at least a couple of good players who can beat you if you let them.
"Those games are never easy," says U.S. forward Landon Donovan, who draws markers almost magnetically against CONCACAF teams. "You can say we should beat them because we're better, but those are the teams sometimes we struggle against. They pack it, get everybody behind the ball, and we're not always as smart or patient as we should be."
There's are incongruities in the 23-man squad Bradley has picked for this tournament. There are players with Gold Cup experience, a la Clint Dempsey and Taylor Twellman (2005) as well as stalwarts like Donovan, Beasley, Pablo Mastroeni, Kasey Keller and Frankie Hejduk. Eddie Johnson played in the 2006 World Cup, but missed the 2005 Gold Cup because of injury.
And there are players like Watford defender Jay DeMerit, whose exclusion from any national team program until this spring renders him virtually unaware of CONCACAF except for the game he played against Guatemala in March.
"It's a matter of us playing the way we can against them, i.e., using our athleticism and height, by getting set pieces or whatever, but also by getting chances early in the game that might open up the rest of the game for us and make it easier," says DeMerit, more accustomed to sleet and speed than the heat and spice he'll encounter in the next 18 days.
"Those teams make it hard for you to break them down. That's not a simple thing to do, break down 11 men behind the ball. That's what we're working on now and we'll continue to do that and we'll be ready."
The pairing of Bradley with Benny Feilhbaber in midfield a few times this year already has numerous observers locking them into place for the next decade, but Ricardo Clark will certainly have something to say about that in this tournament if he gets the chance, and Pablo Mastroeni isn't likely to take up residence in the back line for the USA as he has done the past few seasons for Colorado. Sacha Kljestan is just one of several candidates who will make a case if they are called in for the Copa America.
Still, praise for the Benny and Michael has been deserved. Both earned assists against China, and Feilhaber raced upfield to lob the winning goal in the 4-1 rout last Saturday.
"He's very comfortable on the ball and likes to get the ball with some time and space," says Bradley of Feilhaber. "His choice of passes and where the ball to needs to go and stuff like that is all really good. I can play next to him and work hard and win some balls and then be a guy who helps get Benny the ball in the types of spots he likes to get the ball.
"We're both young and we both have a lot to learn but I think the potential for us to play together both in the national team and in the Olympic team is definitely exciting."
Take note of the Olympic reference.
As tricky as games against CONCACAF teams can be, this tournament provides Bob Bradley with a nearly ideal showcase to display his wares. His style is straightforward but not overbearing. He's meticulous without being persnickety. He will have to adjust personnel and tactics as injuries and suspensions pile up, but that comes with the job. He knows the region, the teams, and how this competition plays out.
Yet he's already raised eyebrows by declaring as many as "eight or 12" Gold Cup players could also be named to the Copa America team, after implying previously two entirely separate squads could be utilized.
Playing in both competitions would require six straight weeks of training and competitive matches and time away from their MLS teams. (Few, if any, European-based players are expected to be on the Copa roster.)
Landon Donovan was the first player to have publicly expressed his preference to play in just one competition, and he and Bradley have already voiced their viewpoints.
"I didn't want to create the impression that I wouldn't play if Bob picked me," says Donovan. "I would never do that. If he picks me I'll go and do whatever I can to help the team win, which is always the way I approach any game with the national team or the Galaxy, for that matter.
"It's a great tournament and it's an honor to play for your country there, like it always is. It's a real crazy summer with the Gold Cup and the Copa America and Beckham coming here and SuperLiga plus the league games, and I want to be with my club as much as possible. That's important for me, too."
The Gold Cup has been important springboards for several players. In 2002, Frankie Hejduk and Eddie Lewis revived their national team careers by helping the U.S. capture the regional title. Defender Jimmy Conrad's contributions to the 2005 crown landed him a spot on the 2006 World Cup team, and his play in Germany was one of the team's few bright spots.
Bradley has used 42 players this year. That number will grow as players like Michael Parkurst make their international debuts.
"It's part of a new cycle, and we've always made decisions based on what we felt was good for the long run, but we always recognize the importance of getting the results on any day," says Bradley. "We feel that so far we've been able to balance those things, and I think the roster we've put together for the Gold Cup reflects our understanding of both ideas."