From Bridgetown to Brickyard: Kyffin Simpson's Rapid Ascent to IndyCar [Exclusive]

Kyffin Simpson calls the island of Cayman home and began racing in Barbados, but his seat at Chip Ganassi Racing next to two IndyCar greats is where he has taken up residence.

Kyffin Simpson Chip Ganassi Racing Indianapolis 500 | Penske Entertainment: Chris Jones

Somewhere in Ohio, there is a fan of Kyffin Simpson who has now found his signature on his face two years in a row. A request like that definitely makes you slowly blink and ponder where life has taken you, but for Simpson, it's moments like these that are the most memorable interactions that he has at the track.

It's a small, funny ask, but it says something real about Simpson's presence in the IndyCar Paddock. At just 21-years-old, he has built a career in IndyCar that far surpasses what the number on his Wikipedia page may suggest. He races for a top team – Chip Ganassi – and his teammates are 6-time IndyCar Champion Scott Dixon and 4-time IndyCar Champion Alex Palou.

Long before the face-signing or the Chip Ganassi Racing seat, though, there was a young child, born in Barbados, raised in Cayman, who didn't even realize that racing was a viable full-time career, let alone one that would take him to one of the top racing series in the world.

Kyffin Simpson sat down with Grand Prix on SI to tell his story.

Discovering the Career of Racing

Simpson won his first karting championship in Barbados at nine years old, but at the time he didn't understand the full breadth of what this would become for him. Racing was a passion, but only turned into his ambition once he understood that people can actually make a career doing it – especially outside of Europe.

"I don't know if I quite knew when I was nine, but racing was kind of around at the time. I didn't really know it could be a job... but then when I found out 'oh, wait, people are making a living doing this' I was like 'well, why don't I do that?'"

Kyffin Simpson, Chip Ganassi Racing

Kyffin Simpson - Acura Grand Prix of Long Beach | Via Penske Entertainment, Paul Hurley

He credits a conversation or two with his father for this stark realization. After all, Formula 1 was the sport that he grew up watching – one with an extremely steep path up and a high barrier to entry.

As for discovering the sport of racing in the first place? That was largely thanks to his friend and now Formula E driver, Zane Maloney. He would sit and watch Formula 1 races with Maloney, looking up to the Iikes of Lewis Hamilton and the rising star of Max Verstappen.

Maloney's allegiance to Lewis Hamilton in the 'Brocedes' fallout became a running joke for the pair. For those who are uninitiated, Brocedes is the commonly used term to describe the fallout between Rosberg and Hamilton during their time as teammates at Mercedes.

Team Abt driver Zane Maloney | IMAGN IMAGES via Reuters Connect

"He's [Maloney] the one that really got me into racing. He was the biggest Lewis Hamilton fan ever, so we always tease him about Nico and mess with him because of that."

Kyffin Simpson, Chip Ganassi Racing

Behind the Hamilton-Rosberg joke with Maloney is a deeper thread to pull on, as well. Both drivers grew up in the Caribbean and found their way to motorsport at its highest level. This is a legacy that Simpson carries into the IndyCar Paddock.

Representing a Region, Not Just Himself

It is no secret that the list of drivers competing today under the Cayman flag begins and ends with Simpson. However, it wasn't just Cayman that shaped Simpson's home. Barbados did as well.

"I raced under the Barbados flag because that was my hometown. A little bit after I started racing in America, I moved to Cayman. Usually when you're filling out stuff it will say 'what's your hometown?' and I just kind of always wrote down Cayman. I still consider that home... they're both home to me."

Kyffin Simpson, Chip Ganassi Racing

Indycar Series driver Kyffin Simpson | USA TODAY Sports via Reuters Connect

This identity carries weight beyond his own career, even if he is forced to choose one nation to represent over another.

Simpson is the first driver from anywhere in the Caribbean to compete in IndyCar, a distinction that he doesn't take lightly given how many drivers from the region never got the same opportunity... including those as close to him as his best friend's home.

"It's just cool representing my country. I raced against Zane's younger brother, Calem, a lot growing up, and he was very good. Unfortunately, Zane was ahead of him. Calem was a great driver, but he just never really got the chance. There's a lot of kids like that in Barbados that unfortunately may never get the chance."

Kyffin Simpson, Chip Ganassi Racing

He added that it is important to him that his success in IndyCar is meant as encouragement for those kids similar to him growing up in Cayman or Barbados. After all, Simpson entered the IndyCar series as 'just a kid' himself at age 17.

Kyffin Simpson, Chip Ganassi Racing, Kite Surfing | Courtesy of Chip Ganassi Racing

That type of responsibility and pull to return home is something Simpson embraces during IndyCar's off-season. Every year, it pulls him back to the beaches and the water of his home island, where he takes up his favorite hobby, kite surfing.

"I've always grown up around the ocean, always being outside and in the ocean. We just get back home around late October, early November when the windy season starts, and any day that it's windy we're out there."

Kyffin Simpson, Chip Ganassi Racing

The 'we' Simpson refers to is his family, the same people who made it possible for Simpson to chase racing in the first place.

The Simpson Family

Kyffin made it abundantly clear that none of this would have been possible without the sacrifices of his parents and sister. This is a narrative that is aired often in racing, but with Simpson racing in America and no 'top series' races in the Caribbean, the sacrifices were greater.

Racing meant leaving Barbados and then Cayman for long stretches of time, splitting the family down the middle to take care of his younger sister. It was rare that the Simpson family was able to support Kyffin and raise Sophia at the same time.

"Racing is not an easy sport to get into, and living in a different country makes it very difficult to then go race in America. A lot of times, one parent would be with me racing, and then the other would have to be home with my sister."

Kyffin Simpson, Chip Ganassi Racing

All of this to say that Simpson is lucky that it has changed now. As I interviewed him, his younger sister, Sophia, watched on in a Chip Ganassi team kit as a member of their Business Operations team.

He and his sister are now both adults, and his parents are able to attend every race together, with a circle of family - some from Barbados and some from Florida - cheering him on. That support system has grown with Simpson all the way to the top of the sport.

Simpson's Teammates of IndyCar Legend

Simpson is currently in his third season racing alongside Sir Scott Dixon, six-time IndyCar Champion, and Alex Palou, four-time IndyCar Champion, at Chip Ganassi Racing. He is the youngest (bar Nolan Siegel, one month younger than Simpson) on the grid, but when he joined the Chip Ganassi program, he was even younger.

Chip Ganassi Racing driver Alex Palou | USA TODAY Network via Reuters Connect

At only 17 years old, Simpson became a development driver for CGR, and while age is but a number, this is only intensified by the pedigree of drivers in the program he joined. For Simpson, though, being younger and less decorated isn't something that weighs on him at all.

"To me, it's always been more about experience in the series than actual age. I've been around people older than me all my life, racing and karting. You're working with mechanics and engineers who are adults... and you're 12."

Kyffin Simpson, Chip Ganassi Racing

I pressed harder on this point, knowing the rhetoric that surrounds Simpson during a race weekend. A driver without a race win in IndyCar with two of the greatest to ever do it? That must weigh on him in some capacity.

However, the point was moot with Simpson.

"We're still both out there racing for a win, at the end of the day. You can't be out there thinking 'oh that's Scott Dixon, six-time IndyCar Champion'. As soon as you do that, you might crash into him."

Kyffin Simpson, Chip Ganassi Racing

Chip Ganassi Racing driver Kyffin Simpson | USA TODAY Network via Reuters Connect

He paused, laughed a little, and added that, frankly, not crashing into his teammates is 'rule number one' at Ganassi – or frankly any team. Truly, what racing beside Dixon and Palou means to him is that he is presented with the greatest opportunity to learn, and it's not what you think.

"Being around him [Dixon] and how he works with the team, and how he's built such a great environment there alongside Mike and Chip. You learn a lot from that and how they conduct themselves with the team. You have to be the leader of the team and lead the team in the right direction."

Kyffin Simpson, Chip Ganassi Racing

When you look at the numbers, although Simpson credits his teammates for interpersonal skills, their tutelage is obvious. In his first season, he finished 21st (2024). In his second season, he finished 17th (2025). Now, he sits 15th in 2026. Simpson is, in all regards, improving as an IndyCar driver.

Simpson isn't concerned with hitting milestones on a timeline or comparisons. He's building his own legacy: One for Cayman, for the Caribbean, for his parents, and for himself... one signed face in Ohio at a time.