The Airborne Aristocrats: Vintage Aircraft Flyovers at Famous Horse Racing Events

Moreno Aguiari
Moreno Aguiari
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“Vintage Aviation News staff did not write this article; the content comes via our partners who wish to help support our website.”

Can you imagine a bigger flex than flying over a major horse racing event? Most of us can’t even afford tickets to these races unless maybe we are willing to sell some bone marrow to buy the ticket. And there’s the richest of the rich, literally looking down on the rest of us, from their own private airplanes. Absurd? Maybe. Over the top? Sure. Lots and lots of fun? You bet. Luckily you don’t need to fly over to know how to bet on Kentucky Derby today as it is available online. Nonetheless, come with us as we take a look at well-known airplane-related stories that have emerged at famous horse racing events.

Flying Michael Jordan At The Kentucky Derby

This is possibly the very best Kentucky Derby story of all time—at least when you consider moments that don’t actually involve horses. For those of you who do not know, Michael Jordan is famous not just for his skills on the basketball court, but also for his enthusiasm for sports betting. He actually received considerable criticism for this in the 80s. Professional athletes betting on sports is always at least a grey area. The situation never developed into a Pete Rose scenario, though, and when you are the best basketball player to ever live you don’t need to worry much about critiques. In retirement, Jordan’s love for sports betting developed into a particularly prominent passion for horse racing. At one point, he even owned his own competitive horse. This story takes place on the day of the Derby. Keep in mind, this is an event that sells out MONTHS in advance. It doesn’t matter who you are—getting a last-minute ticket is next to impossible. Or is it? Michael Jordan put this idea to the test when, on the day of the Derby, he decided he wanted to attend. He flew his private plane into Louisville. Was met with a police escort to the event. There at the ticket booth, his assistant was initially denied seats. There simply weren’t any. MJ walked up to the booth. “Hey! Is there any way you can help us out?” Within minutes, the NBA legend was seated in his own private box. Catered and everything. It’s nice to be the GOAT.

A Jet With Tom Brady And The Pats

Michael Jordan isn’t the only All-Star who shows up to Triple Crown events in style. Tom Brady is yet another sports icon to have developed an intense love for horses. In 2017, Brady flew his entire team out to the Derby in his private jet. No, they didn’t pull an MJ and arrive without tickets or any type of advanced notice. Yes, they did dress in the traditional pastel-colored blazer. Even eight years later, photos of this legendary trip are still widely circulated—particularly this time of year, when the Derby is soon upon us.

Other Airplane Connections

At the end of the day, the best horse racing events are more about what happens on the ground than what happens in the sky. Still, there have been other notable connections over the years. Yes, celebrities and other elite guests often arrive in private aircraft. Some events also make a point of showcasing famous aircraft on or near the venue. They have to find something to do. People come in from literally all over the world for races that take only a couple of minutes at the very most. While these displays are not necessarily a fixture of any Triple Crown Event, they are something to keep an eye out for. There is always lots to do during the week of any major race. If you’re lucky enough to attend, be sure to keep an eye out for fun opportunities in the community.

Enjoy Racing Your Way

It’s so easy to get into the mindset that horse racing is only for the richest of the rich. Tickets to the Kentucky Derby can easily cost several thousand dollars. Other Triple Crown events are more of the same. At these races, celebrities pack the stands in silly outfits that cost more than your mortgage and car payments—combined. In this environment, it’s easy to forget that the vast majority of horseracing is really a blue-collar affair. Average, everyday people heading to the track on the weekend for cheap beer and small bets. Yes, rich people enjoy racing. They might be the ones who can afford to show up to the biggest events in designer clothes, and quite possibly impractical airplanes. That doesn’t mean there aren’t fun racing opportunities for the rest of us. The first leg of the Triple Crown is soon upon us. Plan a fun viewing party. Get some good Kentucky bourbon. Maybe learn how to mix a killer mint julep. Have fun.

 

“Vintage Aviation News staff did not write this article; the content comes via our partners who wish to help support our website.”

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Born in Milan, Italy, Moreno moved to the U.S. in 1999 to pursue a career as a commercial pilot. His aviation passion began early, inspired by his uncle, an F-104 Starfighter Crew Chief, and his father, a military traffic controller. Childhood adventures included camping outside military bases and watching planes at Aeroporto Linate. In 1999, he relocated to Atlanta, Georgia, to obtain his commercial pilot license, a move that became permanent. With 24 years in the U.S., he now flies full-time for a Part 91 business aviation company in Atlanta. He is actively involved with the Commemorative Air Force, the D-Day Squadron, and other aviation organizations. He enjoys life with his supportive wife and three wonderful children.
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