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The Top 5 Holy Grail Watches of All Time
I’ve been really looking forward to this one!
One of the best things about horology is there is nearly always another target to aim at. For many seasoned collectors, it is the thrill of the hunt which drew them to the activity in the first place.
You spend weeks, months or even years in search of that specific model, from the specific year, with the specific dial color or font variation. Finally you track it down and secure it, usually spending cringe-inducing sums of money in the process. Then, human nature being what it is, in time the novelty wears off and it’s on to the next one. And rinse and repeat ad nauseum.
But there’s always that one. That somehow unreachable white whale of a watch; the one which is just too rare, too valuable, too impossible to even imagine possessing, the only one you would never tire of.
These are the ultimate Holy Grail watches. They differ from standard collector targets in that, for many of us, a picture might be the closest we get to ever seeing one in the flesh, let alone buying.
If you’re anything like me, you do a lot more daydreaming about watches than purchasing of them. Some days, I tend to do more daydreaming than actual wearing. And it is the Holy Grails which spend the most time in my head.
The Top 5 Holy Grails
Obviously, and perhaps even more than normal, Holy Grail choices are extremely subjective. For some people (the lucky ones) it might be a humble, mass-produced digital selling for a few hundred bucks.
For our purposes, however, I’m going to stick to the more industry-accepted use of the term; the vanishingly rare, the stupendously expensive and the practically unobtainable.
We’ll be looking at each entry on the list in their own dedicated articles, but for now and in no particular order, here are our top 5.
The Rolex ‘Paul Newman’ Daytona
The whole furor around the Daytona once belonging to Paul Newman coming up for auction hit not long after my own interest in horology started.
It was something of an eye-opener. When you first get interested in luxury watches, generally the only thing you know about them is that they are expensive. You look at the prices of your favorite Rolex or Omega or even Patek and—while they are likely even pricier than you thought—owning one is not out of the realms of possibility at some point in the future, given the breaks.
Then Newman’s Newman goes for the best part of $18m and you realize there are levels to this whole thing. And your own are a long way down the scale.
That 2017 auction was a strange occurrence. The astronomical sum was clearly not paid for the watch itself but because of its former keeper. Had it once been owned by Joe Schmoe, no one would have bid. But Paul Newman was amongst the most famous and charismatic stars of his or any generation and, had my name been Sheikh something-or-other and eighteen mil was neither here nor there to me, I’d have had my hand up too.
Alas, I have to be more conservative with my millions and so the watch went to an ‘unknown buyer, possibly from Asia or the Middle East’ as sources quote.
What has the unknown buyer got themselves though? The Rolex Daytona ref. 6239 with its exotic dial was an unpopular variant of an unpopular watch when Newman’s wife Joanne Woodward bought it for him at some point between 1968 and 1972.
The full stainless steel chronograph was likely purchased at Tiffany’s New York for the princely sum of around $230. As it was a gift to celebrate Newman’s entry into the world of professional motor racing, Woodward had the back engraved with ‘Drive Carefully, Me’.
And that’s about it.
Those first generation Daytonas were something of a sales disaster, hampered as they were by their mechanical hand wound calibers, coming at a time when quartz movements were starting to rear their disruptive heads. Coupled with that, this one had a weird three-color, Art-Deco style dial, its numerals in a non-standard font and with big squares at the end of the totalizer hash marks.
Of course, these days we have quartz technology to thank for steering mechanical watches in a new direction. Transformed out of a Swiss survival instinct into status symbols rather than appliances, chances are those early ‘exotic dial’ Daytonas would have become highly sought-after anyway, what with their scarcity. But with the backing of Hollywood royalty, what are now known as the Paul Newman Daytonas are still some of the most valuable vintage collectors’ items in the business. From their peak around 2023, buying even the least expensive one today still entails parting with six-figures.
Yet, there is only one owned by the man himself, still the second most expensive wristwatch ever sold at auction and, to some, the holiest of Holy Grails.
The Patek Philippe Nautilus ‘Tiffany’
The fabled Patek Philippe Nautilus ‘Tiffany’ came out in 2021 and contributed to a sort of mass hysteria in the watch world.
It consisted of a ‘standard’ ref. 5711 (is there is such a thing as a standard Nautilus) outfitted with a double-stamped dial, featuring both the Patek Philippe and Tiffany & Co. signature, on a face painted in Tiffany Blue; the brand’s proprietary color.
The limited edition model was a meeting of two anniversaries. The unimaginably popular ref. 5711 was released in 2006 to commemorate the 30th anniversary of the Nautilus model itself, while 2021 marked the 170-year collaboration between Patek and the upscale retailer.
Tiffany became Patek Philippe’s first ever authorized dealer in the United States, a relationship dating all the way back to 1851. The affiliation between the two has flourished over the years, even through potentially troublesome ownership changes and the takeover from LVMH. It is fitting then that the 170 units produced of the watch were made available exclusively at the Tiffany & Co. boutiques in New York, Beverly Hills and San Francisco.
As with the Paul Newman above, it is the dial which does most of the work turning this from a merely desirable watch into a Holy Grail. By the end of the ref. 5711’s run in 2022, waiting lists were reportedly 10-years long. Those unwilling to wait could pay truly extortionate amounts on the preowned market, averaging during their 2022 peak at about $180,000, for a watch that retailed at around $35,000.
So it was certainly already a coveted model in whatever configuration it came in. But, add in the two factors of being A. a limited edition and B. associated with one of the most opulent places in the world, and there was always going to be bedlam when it landed.
And there was. The official price was laughable, even with its Tiffany Blue premium, at $52,635. The fact that only 170 pieces would be available told everybody that buying one would involve massive amounts of either luck or cash or both. Sure enough, not long after the launch, examples started changing hands for roughly 60-times the retail, with some clearing the $3m mark.
It’s calmed down a lot since then, and nowadays you barely have to spend more than $1.5m for this steel, time-and-date watch with its outdated movement.
Clearly, as with the Daytona, you are paying for what the model represents, rather than what it is worth materially.
Patek is legendary, the Nautilus is an icon, the ref. 5711 is its most famous iteration and Tiffany & Co. is arguably decadence’s last bastion. Put them all together and we get a Holy Grail.
The Omega Speedmaster CK2915
The two models listed so far technically constitute tool watches; yes, even the Patek.
However, there are tool watches and there are tool watches, and the Omega Speedmaster has always been the latter.
Even the contemporary version, if you hold it up against its nearest natural predator, the Rolex Daytona, it’s the Speedy you can still envisage actually being worn with purpose rather than for clout.
Over the years there have been more than 250 different versions of the Speedmaster, and a fair number of them could realistically be thought of as a Holy Grail for the average fan. The CK2998 from 1959, for example, was the first Omega in space, worn by Wally Schirra. The ST105.003 was the reference to pass all of NASA’s watch-killing tests in 1964 and qualify as standard astronaut issue. And, of course, the ST105.012 and 145.012 were the ones to actually make it to the moon; the former on the wrist of Buzz Aldrin.
Yet, due to its legacy and its scarcity, perhaps the truest grail Speedy is the very first of the breed, 1957’s CK2915.
Like all the greats, this is where we get to appreciate just how enduring pure design genius is. Although there are differences between this origin piece and the modern day equivalent, there are so many shared visuals the resemblance between the two eras is unmissable.
Launched as one third of a trio of tool watches alongside the debut examples of both the Seamaster 300 and Railmaster, the Speedmaster CK2915 measured 38mm, came with recessed sub dials at the three, nine and six o’clock, had the now-iconic Broad Arrow hands and, a first of its kind, engraved its tachymeter scale onto its bezel instead of printing it on the dial.
Underlining its sporty credentials, as well as that highly legible dial, the reference also had a screw down case back which granted a decent 60m water resistance.
Perhaps more significant than all of that though, is what goes on inside. While there are no shortage of watches that get to be called legendary, there are very few movements which achieve the description. The Caliber 321 inside Omega’s inaugural Speedy is one. A genuine column wheel-controlled workhorse, based on the 2310 from Omega’s movement partner, Lemania, the 321 served in the first four major renditions of the Speedmaster. Tough, accurate and beautifully detailed, it was reissued in 2019 inside the Apollo 11 50thanniversary limited edition.
The CK2915 was not limited edition. However, as it was only produced for two years, replaced by the CK2998 in 1959, it is very rare. Rough estimates put the total number produced as between 1,500 and 2000, with fewer than 1,000 likely to have survived into the present day.
That, combined with its status as the first example of possibly the most revered and celebrated chronograph of all time, mean it lives up to its nickname of ‘The Speedmaster to Rule Them All.’
The Breitling Navitimer 809 Cosmonaute Mark III ‘Scott Carpenter’
The Breitling Navitimer is another of horology’s most distinctive shapes.
Designed by pilots for pilots, the Navi was the result of a collaboration between the watchmaker and AOPA, the Aircraft Owners and Pilots Association.
Long before the introduction of sophisticated cockpit computers, an aviator’s watch was a safety device of unparalleled importance, with accurate timekeeping an essential component in calculating distance traveled, fuel burn, navigation and a host of other metrics.
However, all of those computations had to be done in the heads of pilots already potentially working to capacity. What Breitling and AOPA endeavored to create was a watch that could do much of the work itself.
Starting in the early ‘50s, the brand drew on one of their own for inspiration, the Chronomat from 1941. The first watch to include a slide rule rotating bezel, it had been made for mathematicians (CHRONOgraph/MAThématique), allowing for quick and easy calculations and conversions.
By coopting the bezel for the Navitimer, and giving the watch a tricompax layout instead of the Chronomat’s bicompax, Breitling were able to release the quintessential pilot’s companion in 1952. Initially available only to AOPA members, 1954 saw it opened up to the general public.
One of the not-so general public who became a fan of the Navi was U.S. astronaut Scott Carpenter. He had worn a Navitimer throughout his career as a Navy pilot and when, in 1961, he was selected as commander of NASA’s Mercury Project, he approached Breitling with a request. Could they make a space flight-specific version of the watch, with a larger bezel which could be gripped with an astronaut’s heavy gloves, an hour hand which went around the dial only once a day rather than twice, a corresponding 24-hour scale instead of the usual 12-hours, and a simplified slide rule?
Breitling came back with the reworked watch, dubbed the ‘Cosmonaute’ and not the ‘Astronaut’ as you might expect, a deliberate act to symbolize humanity’s shared journey into space. Carpenter made it the first Swiss watch to go into orbit in 1962 aboard the Aurora 7 capsule.
If you look at the market, there are actually plenty of Cosmonautes on offer, and for very reasonable sums. The fabled MKIII, on the other hand, was produced only for a few months and there are thought to be only around 20 examples in existence.
The last one to see the light did so in 2019 and came from the estate of one John Glenn. The hammer dropped at $156,250.
The Breitling Navitimer is a watch that has virtually no equal. It is a true outlier in the industry, one of the toolest of tool watches. Already extremely cool, the ultra-rare space-prepared variant is next level.
The Blancpain Fifty Fathoms Milspec 1
In truth, there are a number of Mil-Spec models we could have chosen as Holy Grail pieces. There’s something about vintage watches that have been associated with the military which captures the imagination of collectors in a big way.
Probably the most famous examples are Rolex’s Milsubs, a run of lightly modified Submariner references which served with distinction among British Special Forces from the 1950s to ‘80s. Sister brand Tudor also supplied the French Navy with their own Submariner ‘MN’ (Marine Nationale) references, the ref. 7016/0 and 9401/0, for many years.
Panerai, Omega, Breguet, Longines and others have all issued military specification watches through the years. But among the most prominent remains the Blancpain Fifty Fathoms Mil-Spec 1
At its heart, it is a standard Fifty Fathoms, one of the very first dedicated dive watches ever made. The combined efforts of two French World War II officers, Captain Robert ‘Rob’ Maloubier and Lt. Claude Riffaud, and the CEO of Blancpain, Jean-Jacques Fiechter, brought us the debut reference in the mid-‘50s.
Tough as nails, easy to read, and with a handy rotating diving bezel, the Fifty Fathoms was adopted as standard-issue in the French Navy.
Yet, when Blancpain approached the U.S. military with the watch, things got a little more complicated. To begin with, the Buy American Act stipulated a 25% tariff on watches not made by American brands. That meant Blancpain could not supply the Navy directly. Fortunately, the company’s American distributor, Allen V. Tornek was able to get around the regulations by building a small testing laboratory in the States so the watches were technically tested on U.S. soil.
The other problem was one of functionality. U.S. Navy specs for their dive watches demanded they have moisture indicators to show whether the water resistance had been compromised. Fiechter’s solution was to fit a small bi-colored disk above the six o’clock, one half pale blue, the other red. If any water encroached, the blue half would also turn red, showing the problem.
As you might imagine, as these models were made primarily for the military, they are exceedingly rare. Production would have been limited to begin with, perhaps no more than 2,000 ever being made. Then you have to factor in those pieces which were lost or destroyed on active service, and those which survived are very unlikely to be in all original condition.
That leaves the remaining examples as in-demand as they come, and prices start well north of $40,000. If you find one in mint, unaltered condition, expect $100,000+.
For some, the Fifty Fathoms will always be the father of the modern dive watch. And the military grade examples remain the Holy Grails.
Featured Photo: Mixed art by Oriol Mendivil for BKT Archive.
