Joseph Pilates designed the Cadillac, which was the largest apparatus he ever invented. Due to its size, the Cadillac was not a practical addition to a home gym. It drew inspiration from converted hospital beds and massage tables and received its name as a tribute to the luxurious automobile brand, Cadillac. Pilates himself regarded this apparatus as the finest of his creations. On the other hand, alternative sources propose a different origin for the name "Cadillac." According to these accounts, a client attending a presentation once asked, "Hey Joe, is that your new Cadillac?" when they saw the table, and the name stuck.
Pilates crafted all of his equipment, including the Cadillac, in his basement. The development of the Cadillac may have been influenced by his work with Eve Gentry, one of his clients who also happened to be a predecessor in the hospital environment following her mastectomy. Another theory posits that the trapeze component was inspired by Pilates' father, who was an amateur gymnast, or possibly by his early clientele. Regardless of its origins, it is certain that the trapeze was refined in the mid-1950s to early 1960s.
The Cadillac boasted various spring attachments for arm and leg exercises, a roll-back bar, and a wooden bar that could be pushed through the upright poles to facilitate stretching and resistance workouts. On top of the metal frame, additional attachments included foot straps for hanging exercises and a trapeze with springs. Students would often be seen "hanging" as they gripped the steel bars and secured their ankles in what resembled "padded subway straps." For more advanced workouts, the Airplane Board could be attached. Unlike the Reformer, the Cadillac offered a stable surface for exercises, allowing for a wide range of positions, including upside-down hanging.