Money for Love


The documentary The Gentleman Driver follows four amateur race car drivers who pay to compete alongside professional drivers. Just as these amateur drivers spend money to race, one amateur chess player likewise sponsors an annual event where he plays chess with professionals. Some amateurs spend millions to compete in the sports that they love, money that they earned from being extraordinary businessmen.

Race cars - Photo courtesy of The Gentleman Driver
Race cars
Courtesy of The Gentleman Driver

In some classes of endurance racing, each race team must have one amateur driver. This “gentleman driver” races for a certain amounts of time, such as 45-minute stints, in his team’s race car. Endurance races range from six hours to 24 hours. For the privilege of racing cars alongside professional drivers, each amateur contributes up to $5 million to his team per racing season (8 to 10 races).

Gentleman drivers have successful careers in the business world and are seeking new challenges in racing. They enjoy learning from and hanging out with the professional drivers. One scene in The Gentleman Driver showed professional drivers walking their gentleman driver teammate around the race track, before the race, telling him how to approach the curves. In another scene, a gentleman driver mentions how great he feels when he races well and one of his pro teammates compliments him.

Track Walk - Photo courtesy of The Gentleman Driver film
Track Walk
Courtesy of The Gentleman Driver

While chess may not have multiple amateurs each contributing up to $5 million annually, it does have at least one significant patron. Rex Sinquefield made his fortune managing money and then founded the Saint Louis Chess Club. He estimates that he has contributed $50 million to chess. At the Saint Louis Chess Club, there is an annual event called “Ultimate Moves.” Two amateur players, Rex Sinquefield and his son Randy Sinquefield (owner of Spectrum Studios), lead teams of six professional players. The format is six games of game in five minutes (with a five-second increment). Within each speed chess game, each team’s players rotate after every five moves. For example, on August 16, 2018, Rex Sinquefield began with White in game one versus Randy. After they played the first five moves of a Ruy Lopez opening. Rex’s teammate Grandmaster Wesley So and Randy’s teammate World Champion Magnus Carlsen continued the game. The other professional players commented live on the current positions or, as the commentators called it, “trash-talked.”

Commentator Woman Grandmaster Jennifer Shahade mentioned that she was rooting for Rex’s team, since she is Rex’s chess coach. Like the amateur drivers, who train with racing simulators or at driving schools, Rex prepares for his annual Ultimate Moves chess games.

Thus Rex and Randy Sinquefield resemble the four amateur race car drivers featured in The Gentleman Driver film. In both chess and racing, an amateur joins a team of professionals. In chess, one Sinquefield and six professional players took turns steering their side of six chess games. In 2018, Team Randy won 3.5-2.5 versus Team Rex. Likewise, a gentleman driver takes turns driving a team’s race car with two professional drivers.

Randy Sinquefield (on left) with Grandmaster Levon Aronian - Courtesy of Saint Louis Chess Club, Lennart Ootes
Randy Sinquefield (on left) with Grandmaster Levon Aronian
Courtesy of Saint Louis Chess Club, Lennart Ootes

Among many other chess projects, Rex finances the annual Ultimate Moves event. Each gentleman driver finances his race team and one gentleman driver additionally organized an endurance race event (6 Hours of Mexico). In a video of the 2018 Ultimate Moves event, it appeared that Rex and his son Randy enjoyed competing with, learning from, and socializing with professional chess players. Likewise, each gentleman driver mentioned competition, learning, and friendships as reasons for racing. Most important, the amateurs love the activity itself: playing chess and racing cars.

The word “amateur” has a Latin root meaning “to love” or “lover.” Definitions of amateur include someone who pursues a sport on an unpaid basis. Amateur sometimes means inept. In The Gentleman Driver film, the amateur drivers were more likely than the professional drivers to crash their race cars into the barricades, sometimes causing hundreds of thousands of dollars of damage. Rex Sinquefield has likewise sometimes crashed his team’s chessmen. In game 2 in 2018, Rex blundered in the following position as Black.

chess diagram

Best for Black is to stop the checkmate with 40…Bg5, which leads to an equal game. Unfortunately, Rex chose 40…Qe5? Can you find White’s checkmate-in-one?

Magnus Carlsen and Rex Sinquefield
Rex blunders with 40…Qe5
Courtesy of Saint Louis Chess Club, Lennart Ootes
WIM Alexey Root, PhD

Alexey Root is a Woman International Master and the 1989 U.S. Women's chess champion. Her peak US Chess rating was 2260. She has a PhD in education from UCLA. You can find her books on chess on

One Response

  1. L. Reed
    L. Reed at

    What a great article! I love to watch racing (F1) and I love chess; the comparison between the two is fantastic. Very well done!