It's an unusually temperate Sunday morning in Forrest Hills, Queens, the former home of the last Grand Slam tournament on the tennis calendar. Inside one of the many parking garages dotting Queens Boulevard stands the tournament's 2003 champion. Not that you would be able to tell.

Andy Roddick is wearing a fake mustache and a wig, his blue GEICO T-shirt and GEICO baseball cap matching those of his companion, New York City influencer Danny Mondello. The duo are welcoming US Open ticket holders with free parking courtesy of GEICO under the aliases of Danny and Manny.

"This a beaut here," Andy, or Manny, tells a couple as Danny helps them out of their car. Danny slips in the driver's seat, Manny tossing him the keys before joining him on the passenger side. The director yells cut, and the two hop out and reset as the next car comes down the ramp.

GEICO Serves New York Campaign

Roddick teamed up with the largest auto insurer in New York for the GEICO Serves New York campaign, going undercover with Danny, best known for food account Meals_by_cug, to give tennis fans a free shuttle to the US Open from the parking garage along with giveaways and GEICO swag.

While on the shuttle, the duo chatted with passengers, asking them about some of their favorite players. Some fans named Roger Federer. Others named Pete Sampras and Andre Agassi when asked about their favorite Americans. One passenger even went so far as to name Robby Ginepri.

When someone brought up Roddick's name, Danny was quick to chime in. “He won once," he joked. “It’s pathetic. Win once, lose most, that was his slogan.”

The Journey to Commentating

Roddick later revealed himself to the delight of the passengers, going down the line handing out high-fives before seeing them out. It's not long before he's rushing off to Flushing Meadows for his shifts as a tennis analyst at the US Open for ESPN and ABC.

The 44-year-old has received high praise for his analysis throughout the tournament, with many fans taking to social media to applaud his high tennis IQ and express their wish for him to do more. While he makes it look easy on television, Roddick recalls his earlier experiences as a commentator being an entirely different beast. The sheer scale of the broadcast hit him for the first time when he was up in the broadcast booth watching Iga Swiatek play Jessica Pegula in the US Open quarterfinals back in 2024.

"It was just crazy to me that there was this whole kind of scene going on while they were kind of performing in a silo," Roddick later tells me.

We're sitting in a black escalade, leaving Forrest Hills for the Open in Flushing Meadows. Despite the long morning of filming, he's upbeat, offering me a seat next to him so we can talk. He's reclined a bit in his seat as we head out, adjusting his Psycho Bunny cap while steadying his backpack on the car floor.

In that moment, he doesn't strike me as the former World No. 1. He's just a man eager to share his passion for the sport that gave him everything. That passion has only grown with broadcasting.

"It's fun to actually see people with playing styles that were nowhere near what I could do or was capable of," Roddick said. "Watching Carlos and then trying to have to kind of pull back and say, ok, what would you do if you had all these options?"

Roddick admitted he reached out to several players-turned-commentators for advice, including former World No. 1 Jim Courier, whose commentating style Roddick believed "changed the commentary game." He also reached out to former professional tennis player Mary Carillo, who advised him to make sure what he said on air was important to the context of the match playing out.

"I was not shy about reaching out for advice," he admitted. "Also, [to] people that I know well so they could tell me the annoying parts of my personality I should maybe keep muted."

The State of American Men's Tennis

Since Roddick's retirement from tennis, American men's tennis has been in somewhat of a lull. The generation of John Isner and Jack Sock won two Masters 1000s titles between them. The subsequent generation of Taylor Fritz, Frances Tiafoe, and Tommy Paul brought American men's tennis back into contention, especially after Fritz' first Grand Slam final at the US Open in 2024. A younger crop of American men like Learner Tien and Ben Shelton promise even more.

"It's been fun to watch the progression," he said. "It's always fun to see the younger groups push the group in front of them like Tiafoe, Tommy, and Taylor. I've kind of fully always bought into the creation of a healthy jealousy."

Why, then, with all this talent have American men struggled to breakthrough to that coveted number one ranking? Struggled is maybe not the right word, he tells me.

"Most countries would be so happy with where we're at," he said. "When three guys take up 60 some odd slams, there's not a lot of real estate left."

This year's US Open may just be the turning point. For the first time in 31 years, five American men advanced to the fourth round of a Grand Slam.

"It's the first time we've had that many since 1995," Roddick said. "That would suggest progress...we keep having the conversation, but it just looks a lot different. There's a lot more progress being made, and I think it's good that maybe there are multiple shoulders for this conversation."

Progress is certainly one word for it. After Shelton's four hour and 28 minute five set win over Carlos Alcaraz and Tiafoe's epic comeback over Alex Michelsen from two sets to love down, an American man is guaranteed to play the 2026 US Open final on Sunday.

No American man has won a Grand Slam, much less claimed the number one spot in the rankings, since Roddick. It's entirely possible one of these men will be the first American man to lift a Grand Slam title in 23 years.

"The mental discipline of Foe and the mental discipline of Ben Shelton are the reasons why they're playing in the semifinals with a shot at a US Open title," Roddick said a few days later on his podcast Served. "Whichever one it is, they need six sets. Six sets left."