Just by watching our doc, Winning,  you can get a real sense of Paul Newman’s sense of style and love of competition. That spirit lives on as his beloved Daytona watch goes up for auction later this year. The sale may result in the item being classified as the world’s most expensive Rolex watch.

On October 26th, the iconic piece will head to the Phillips’ New York Watch Auction: WINNING ICONS — Legendary Watches of the 20th Century.

Paul’s in classy company: other legendary watches on the block include those owned by Jackie Onassis, Bob Hope and even Al Capone.

This Newman Daytona was owned by Paul himself, but is actually part of an entire line of high-quality Daytona watches. It’s currently appraised at $1 million, but may generate enough excitement to demand an auction price as high as $5 million.

Celebrity-owned watches are always an exciting part of any world-class auction. However, this watch has special significance: it was never sold publicly before, and the piece Newman owned earned the mythic nickname, the Paul Newman Daytona.

Newman’s wife, Joanne Woodward, gave him this Daytona as a gift when he began auto racing in 1972. Her inscription on the back: “Drive Carefully Me.”

In helping us understand the aesthetic meaning and beauty of the watch, the online magazine dedicated to high-quality watches, Hodinkee, says:

The Paul Newman is so desirable for so many reasons, one of which is the undeniable fact that the thing is just downright gorgeous. The playfulness of the dial is so beautiful, so very un-Rolex. On the wrist, a Paul Newman is hard to match. And, because it’s so well known, they are about as liquid as any watch in the world, even at the astronomical prices that we see now.

The post also goes on to say that there is no technical difference between a Paul Newman Daytona and a basic Daytona beyond the type of dial it features. As well, there are more fake Paul Newman dials in circulation than there are real ones, so care must be taken — and expert advice sought — when purchasing.

Here’s how to tell the real thing:

Original name: Rolex Cosmograph Daytona Oyster

Reference numbers: 6239, 6241, 6262, 6263, 6264, or 6265. (6239 is the one that Newman owned.)

Color combos: there are only four of them. A “panda” dial with black background and white chronograph totalizer subdials; an inverse panda with white background and black chronograph totalizers; an inverse panda with cream-colored background and black chronograph totalizers; anthracite-colored background with white chronograph totalizers.

“Exotic” dial: a red scale which circles the perimeter of the dial.

Proceeds from the sale will go to the Nell Newman Foundation (Nell is Newman’s daughter). The foundation awards grants in ten core program areas: environment, education, arts & culture, spiritual, scientific, human services, emergency relief, animal welfare, and international affairs.

Click here to check out Winning: The Racing Life of Paul Newman. You’ll then truly understand what puts Paul Newman in the driver’s seat.