The Paul Newman Daytona - next to the Submariner range, this is of the most well-known collectible Rolex watches out there. There is a sort of mythos around the watch given the ambiguous connection to the movie star/pop culture hero, and the extreme fame that the Daytona collection later had. The story of the Paul Newman Daytona is a bit convoluted and complex. There was not just one watch, and Rolex never officially called any piece the Paul Newman Daytona.
Unlike some people out there I am not an expert of Rolex watch history or Rolex collecting. In fact, the high-prices that some Rolex watches fetch at auction make me chuckle. For a better historical observation of the Paul new Daytona I will defer to my friend Jake at RolexMagazine.com. He wrote a nice summary of the Rolex Paul Newman Daytona here.
My favorite part of the Paul Newman Daytona story refers to the indeterminable nature of collecting. People today strive hard to predict what will become a collector's item - and that is really hard to do. When this watch and its kin came out, they were most sales failures. There are a few reasons for this, mostly due to the style and the movement. In the 1960s you had automatic chronographs coming out on the market - and everyone wanted one. So this watch that had a reliable, but manually-wound chronograph wasn't appealing. There is a also a reason the Ref. 6241 has what people call the "Exotic Dial." Few Rolex timepieces have dials with this style and it was a unique design for the brand. Today people generally agree that the look and feel of this (supposedly) race-themed dial is a classic.
Rolex never made that many Paul Newman Daytonas as they didn't sell well. This created rarity, which now translates into value. It was difficult at the time to guess that a watch that couldn't sell would be so desired, but that is the way it went. So if you are trying to predict what pieces today will go up in value? It isn't always a bad idea to find nice, but highly discounted watches that have something a but special to them.
The Paul Newman film Winning had Newman wearing one of these Rolex ref. 6241 watches on the poster. I believe that Newman did not wear the watch in the movie actually, but he did own one and you can see him wearing it around in various pictures taken during his life. He seemed to like it off the bracelet on a sort of bund strap.
Today this Daytona model is among the most popular collectible Rolex watches on the planet. They are very rare and go for big bucks when auctioned. This particular piece available on James List seems to be in excellent condition and was made in 1964. It isn't super large at about 37-38mm wide in steel. I have a feeling that Rolex will come out with an homage dial in the next couple of years to remind us of this classic clean style that still has a bit of avant garde style to it. The post on James List mentions "Price on Request," but I hear from the seller that they will part with it for around $90,000. See the result of a Sotheby's auction where another Ref. 6241 got 110,500 Swiss Francs (more in dollars) here.