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“I MADE THE MISTAKE, NO ONE ELSE,”  says former Hollywood power agent Michael Ovitz of the several dozen custom watches he commissioned from Patek Philippe about six or seven years ago. It was the first time Ovitz, who has been collecting for 35 years, placed a bespoke order, but his goal was ambitious: He requested several different references, each in a variety of metals, with one-of-a-kind dials. “They were terrific,” he says of Patek, “and accommodated everything I wanted.”

His regret is not foreseeing two problems. The first was misunderstanding his own psychology: Too afraid he’d bang up his special treasures by wearing them, he never even took some of them out of the packaging. In hindsight, he says he would stick to one version of each reference. “My second mistake was that I didn’t ask them for an exclusive on the design,” says Ovitz. “So I saw a lot of [Patek] watches showing up with my design, and I didn’t want that. I wanted unique pieces.” (Patek Philippe declined comment, citing clients’ privacy.)

Navigating the pitfalls of the world of bespoke watchmaking can be tricky, even for experienced collectors like Ovitz, who also has a major trove of modern and contemporary art. Commissioning can lead to the ultimate in bragging rights—influence over a genius creator’s oeuvre and legacy—or total dejection. Nearly every luxury firm is capable of taking customization to the next level for those willing to spend whatever is required, which can run to millions, but when the client’s and the brand’s expectations are not aligned, the project can backfire.

Ovitz’s response has been to part company with some of the Pateks, recognizable for his “MSO” initials discreetly placed at six o’clock. Several have quietly popped up on the market, both privately and publicly, through notable auction

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