Renowned for its elegance and exclusivity, the Mercedes-Benz 280 SE 3.5 Cabriolet has long been celebrated as a modern classic. Combining timeless design with exceptional engineering, it delivers superb road manners and effortless performance, making it a perennial choice for those seeking a classic with style and substance.

In the summer of 1971, Frank Sinatra accompanied his daughter Tina to a Beverly Hills Mercedes-Benz showroom in search of a special gift for her 23rd birthday. Once inside, they were immediately captivated by this 280 SE 3.5 Cabriolet, a sought-after late-production example equipped with a floor-mounted shifter. As it was the only model present in the dealership with that feature, Sinatra made sure his daughter drove that very car home, beginning a cherished 15 years together.

Over the years, Tina Sinatra enjoyed her gift conscientiously, adorning it with personalized license plates reading “IT!”—a subtle nod to her Italian heritage. In 1981, after reportedly sustaining damage while in Palm Springs, she chose to have the car refinished in black, replacing its original Tobacco Brown. Sinatra continued enjoying the car until about 1985 when she sold it to her neighbor, Hollywood producer Lawrence Gordon.

Gordon kept the Mercedes through about 2002, reportedly entrusting its care to respected Southern California Mercedes-Benz specialist Scott Meinick. Following a change in ownership, Mr. Meinick continued to care for the car both cosmetically and mechanically.

Thoroughly enjoyed and lovingly maintained, the car’s Cognac leather offers a rich, inviting patina while its odometer shows 44,531 miles at cataloguing time. It is accompanied by a Cognac convertible top boot, tool kit, and owner’s books and manuals.

As more of these legendary cabriolets emerge freshly restored, it is a pleasure to find a lovingly kept Southern California example—especially one with the provenance of a true American icon.