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'Antiques Roadshow' guest struggles to speak after expert reveals the value of his 1958 sports flag

The history attached to the flag is tragic, and it personally affected the guest.
PUBLISHED MAR 30, 2025
Screenshots showing the expert and the guest on "Antiques Roadshow." (Image credit: YouTube | Antiques Roadshow PBS)
Screenshots showing the expert and the guest on "Antiques Roadshow." (Image credit: YouTube | Antiques Roadshow PBS)

Any sports fan is emotionally attached to memorabilia and merchandise related to a star or a team in a way that others can't understand. That was how it was for a self-proclaimed ‘speedway sparkplug,’ which means a motorsports fan who appeared on “Antiques Roadshow.” The guest brought the signed checkered flag of the 1958 edition of the Indy 500.



 

The Indy 500 is one of the biggest events in motorsports anywhere in the world. The Indianapolis Motor Speedway, also known as the Brickyard, has played host to some of the greatest races of all time, during this event. The guest grew up only a couple of miles from the track, and motor racing was his passion. This checkered flag that he brought had the signatures of 31 drivers who took part in the event that year, along with those of 18 former winners and dignitaries.

Screenshot showing some of the signatures on the flag. (Image credit: YouTube | Antiques Roadshow PBS)
Screenshot showing some of the signatures on the flag. (Image source: YouTube | Antiques Roadshow PBS)

“As far as I know, it’s the only flag of its sort,” the guest said. However, it had a tragic story attached to it. Motor racing is perhaps the most dangerous sport in the world, and back in the ‘50s, driver safety was nowhere near the level that it is today. In the 1958 Indy 500, a driver named Pat O’Connor lost his life as a result of a freak accident on the very first lap.



 

It turns out that the guest knew O’Connor as well, thanks to his father, who did taxes for some of these drivers. The late driver was one of them, and one day, he and his mechanic came to his house to get their taxes done. The year was 1956, and that year, the guest was taking part in the Soap Box Derby. As a result, he had to build his own car.

O’Connor and his chief mechanic, Ray Nichels, not only decided to take a look at his car but also fine-tuned it as much as possible, especially with the tyre alignment. “They spent time, and they got my tyres aligned, and I raced my car, and I got more speed out of it in Soap Box Derby thanks to Pat O’Connor,” he revealed.

Screenshot showing the expert and the guest on
Screenshot showing the expert and the guest on "Antiques Roadshow." (Image source: YouTube | Antiques Roadshow PBS)

His passing must have been hard for the guest, who clearly had a lot of respect for the driver. That Indy 500 was won by a driver named Jimmy Bryan. While all the over drivers and other people had their signatures in the white spaces of the flag, the race winner had it inside the red pegasus in the center. This was odd since usually, everyone signs the flag, and then the winner signs it once again in the center.

However, there was no autograph by Bryan on it, apart from the one in the center. The signing of these flags took place a few days before the race. This was proven since O’Connor’s signature was in one of the white spaces. “To this day, I don’t know,” the guest said when asked about it.



 

It was now time for the flag to be appraised. The owner had purchased it from a photographer for around $1,000 and believed it to be worth $3000 to $4000. The expert, however, said that he would put a value of $10,000 on it. The guest was in disbelief upon hearing this as emotion took him over. “Wonderful, wonderful,” he said. “Well, it’s a part of my growing up, and it’ll be passed on to my son.”

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