[9][10][11] The couple spent an extended honeymoon in Europe, where Cunningham won a concours with a Mercedes Benz SS delivered to him personally by Rudolph Caracciola.

During World War II (WWII) he tried to enlist in the US Navy but was deemed ineligible due to a combination of age and a pre-existing condition.

[15] At seventeen he joined the Pequot Yacht Club and began to race Star Class boats.

[3] Cunningham bought the schooner Brilliant from the Coast Guard after WWII, and modified it in an attempt to increase its speed.

Cunningham was part of the syndicate that commissioned construction of the 12 meter sloop Columbia to contest the first post-war America's Cup race in 1958.

[20] The original choice to skipper Columbia in the America's Cup was Cornelius "Corny" Shields, but when he was sidelined by heart troubles Cunningham stepped in and led the boat and crew to victory.

[25] Cunningham's racing team arrived at the track accompanied by a large transporter that was both extensively and lavishly equipped, along with the drivers, a retinue of professionals and mechanics, and the cars.

[26] 1955 was the last year that Cunningham built his own cars, the company having run out the five-year grace period that the Internal Revenue Service allowed low-volume manufacturers to become profitable.

His final professional race was in a Porsche Carrera GTS (Type 904) at Sebring in 1966 with John Fitch and Davey Jordan.

The car had a custom frame and was powered by a Ford Model T inline four-cylinder engine with a 16 valve, double-overhead camshaft Frontenac "Fronty" cylinder head.

[30] Cunningham had Phil Shafer modify the car by lowering the Buick Straight-8 engine and moving it back in the chassis.

The body and radiator came from a wrecked Mercedes Benz SSK, and were adapted to the Buick chassis by Byron Jersey.

After receiving a 1949 version of the Straight-8 and chassis modifications suggested by Buick's vice president of engineering Charles Chayne, the car appeared at Watkins Glen the next year with Cunningham driving to a third-place finish.

[36][12] Changes to the car were minimal, and included a dual-carburetor intake manifold, brake cooling ducts, a second fuel tank, and extra lights.

[40] To prepare for his next attempt at Le Mans, Cunningham bought the Frick-Tappet Motors company and relocated the operation from Long Island, New York to West Palm Beach, Florida, renaming it the "B.S.

[47] The final B. S. Cunningham company car model abandoned the Chrysler V8 for a 3.0 L four-cylinder Offenhauser from Meyer & Drake.

Cunningham's supercharged MG TC appeared alongside the Bu-Merc at the inaugural Watkins Glen Grand Prix in 1948.

In 1949 Cunningham partnered with Alfredo Momo, and bought Ferrari 166 Spider Corsa 016-I from Luigi Chinetti.

[27][50] This was the second Ferrari in the US, the first being a Tipo 166 MM Touring Barchetta, chassis 0002 M, sold to Tommy Lee in Los Angeles in the first quarter of 1949.

At the 1954 24 Hours of Le Mans Cunningham fielded a Ferrari 375 MM with experimental water-cooled drum brakes.

[54] Chassis 3053 finished third overall on its debut race at the 1955 12 Hours of Sebring, driven by Bill Spear and Sherwood Johnston.

In 1958 Cunningham fielded two Lister-Jaguar "Knobbly"s. Prepared by Alfredo Momo, the pair delivered an SCCA C Modified championship in 1958.

[56] For 1960 the displacement rules for Le Mans were changed to permit cars with engines larger than 3.0 L. With GM's tacit support and with assistance from Zora Arkus-Duntov, Cunningham began preparing a trio of Corvettes for the race.

[57]: 293–299  As a trial before Le Mans, two Momo-prepared Cunningham Corvettes were entered in the 1960 12 Hours of Sebring, but neither car finished.

In August 1960 Cunningham bought a Maserati Tipo 60 "Birdcage", that he drove in the 1961 24 Hours of Le Mans with co-driver Jim Kimberly.

The entrant of record is the Momo Corporation, and the car was driven by Walt Hansgen, who crashed on lap 14 of his F1 debut.

[59] A Fiat-Abarth 1000 Bialbero Competition coupe owned by Cunningham, prepared by Alfredo Momo's Momo Corporation, and driven by Bruce McLaren won the 1961 3 Hours of Sebring for Grand Touring cars up to 1 L.[60] Cunningham entered two Maserati Tipo 151 coupes in the 1962 Le Mans, along with a Jaguar E-Type.

Over the course of his life Cunningham amassed a large and varied collection of automobiles, including many of his own former racing cars.

After relocating to the West Coast, he purchased a property at 250 E. Baker Street, Costa Mesa, California and established the Briggs Cunningham Museum to house his collection.

Expected changes to capital gains tax laws prompted Cunningham to consider closing the museum in late 1986.