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How I'd Spend $100K First, I’d Buy A Black Bay 58. Then I’d Overdose On Cartier

I didn't forget about vintage Rolex or Heuer either.

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Sarah decided how she'd spend $100,000  a couple weeks ago, and now, I'm the fortunate recipient of this fictional sum to spend on watches and watches alone.

My first move: Search recent auction results for the Rolex 6062 moonphase to see if I could afford one, since it's obviously the best watch ever made. Quickly realizing $100K still wasn't enough for my elusive moonphase, I started thinking harder about how to build a collection.

Like in Sarah's first installment of How I'd Spend $100K, prices are approximate, rounded, and tax-free, because what's a few grand between friends? That said, I did not assume I could just walk into my local Rolex AD and plop down a fresh $15,000 for a Daytona (or something like it) at retail – even my fantasy world isn't that fantastical.

As I built my collection, I consulted our in-house expert advisor and vintage nerd, Rich Fordon, for his opinions and advice. Rich and I are both from Chicago and go way back, bonding over a mutual love of vintage Movado and the Chicago White Sox before either of us ever worked for Hodinkee. I figured if I'm going to have an advisor help build a collection, it should be someone who knows my taste – and honestly, who shares it.

Okay, let's get to spending.

Tudor Black Bay 58 Navy Blue
black Bay 58 navy blue

I still think about when James paired the Black Bay 58 with an MN-style NATO strap in his hands-on review

In my Midwestern practicality, I'm going to start with an everyday watch (For this exercise, I'm assuming I have nary a watch to my name, not even two G-Shocks to rub together.) But since I suddenly now want to spend $100K of my not-so-hard-earned money on watches, I'd better start with something I actually want to wear every day. For that, I turn to the Tudor Black Bay 58 Blue. I own the Black Bay 58 now (in black), but I like the blue more, and since we're starting from scratch that's my choice. On the bracelet, of course. Cost: $4,000. Remaining: $96,000

Cartier Tank Asymetrique Yellow Gold CPCP
Cartier Tank Asymmetrique Yellow Gold CPCP

I prefer this 1996 CPCP Asymetrique to the 2020 limited editions because of the smaller size and the cleaner look of the traditional lug-strap attachment.

When I asked Rich to advise on my collection, he said I should spend "$15,000 to $25,000 on a nice dress watch." Perhaps Rich underestimated my love for dress watches or perhaps I'm just one of those clients who should better heed the advice of his expert advisor, but I decided to spend substantially more on a Cartier Tank Asymetrique in yellow gold, specifically the limited edition of 300 Cartier made in 1996 as part of its CPCP collection.

With apologies to the Cartier Crash and my own Cartier Tank, the Asymetrique is my favorite dress watch ever. I figured if I have $100K to blow on watches and watches alone, I'd better at least have my favorite dress watch in my collection.

And here's what else Rich might not know: I actually wear dress watches a lot, like four to five days a week a lot – what can I say, I think dress watches pair well with sweatpants. So while I might have that Black Bay 58 as my "everyday wear," I'll wear my Asymetrique just as much.

Yes, it's way too much money to spend on a time-only Cartier in yellow gold, but I love it. I love the skewed shape, the guilloche dial, the fact that no other watch looks like it. Cost: $40,000. Remaining: $56,000

Rolex Datejust 6305 in Steel
rolex datejust 6305 steel

Red "Datejust" text, an original roulette date wheel, and a white-gold bezel – the details that make an early Datejust a timeless sleeper from the '50s. Image: Courtesy of Bonhams

At this level, many collections will have a Rolex slot, and I struggled with how to fill mine – so many options. As Sarah said, "there may be no human experience as satisfying as looking down at one's wrist and beholding a Rolex Day-Date."

I guess that's true, but perhaps I'm more of a "simple things" kinda guy than Sarah "Tutti-Frutti" Miller, because to me the simple pleasure of a steel Oyster case in 34 or 36mm is much more enduring than that of a Day-Date. So I decided to spend my money on an early Datejust. Sure, I thought about spending more on a 1016 – hell, Rich told me to buy a mighty 1016, though he did deliver this advice while checking the time on his own (I must admit, beautiful) gilt-dial 1016. So, grain of salt.

I mentioned the 6062 at the beginning, and '50s Rolex is my favorite Rolex, so I wanted something from this era, when Rolex figured out the perfect balance between sport and elegance. Why not an early Datejust, where it (kind of) all began for modern Rolex? I'd want a steel one, and with this type of cash I'm going to wait around for one with a bracelet, perfect patina, an original roulette date wheel, and a bit of extra sauce, like a honeycomb dial or red "Datejust" text, and if I'm lucky, box and papers.

Yep, something like this:

rolex datejust 6305 steel

Image: Courtesy of Christie's

rolex datejust 6305 steel

A 6305 sold through the Hodinkee Shop

Cost: $14,000. Remaining: $42,000

Audemars Piguet Ultra-Thin Perpetual Calendar in Yellow Gold
Audemars Piguet perpetual calendar 25657

An AP QP ref. 25657 in yellow gold – the reference was among the ultra-thin perpetual calendars AP produced in the '80s and '90s. Image: Courtesy of Loupe This

Perpetual calendars are so anachronistically un-useful that I feel I absolutely need one, and I still think neo-vintage offers some value, particularly when it comes to complicated watches like ultra-thin perpetual calendars. In 1978, Audemars Piguet started the whole ultra-thin perpetual calendar trend, and after trying on a lot of these perpetuals, it's still my favorite (3940 fans, I'll see you in the comments).

Rich had tried to sell me on Breguet perpetual calendars from this era, but to me the AP's design is just better. The Jacqueline Dimier-designed case, with its stepped bezel and short, curved lugs, is perfect. Forget Genta, give me a Dimier design every day. Cost: $17,000; Remaining: $25,000

Heuer Carrera 2447N
heuer carrera 2447n

A Heuer Carrera 2447N from the 1960s 

I hate the cliches that say "oh you need a Speedmaster or you're not a real watch collector," or whatever else it might be. But a collection without a chronograph, specifically in my case a manual wind vintage chronograph, felt like an omission. I love winding them. I love wearing them. I love timing random stuff.

To me, the Heuer 2447N has always been the purest expression of a mid-century chronograph. Clean dial, no bezel, sharp case, and a design straight from the hand of Jack Heuer – it's all you need.

"It's the best chronograph," from this era, Rich said, adding that, with the $15,000 I've allotted here, I can wait around for a particularly sharp or unpolished example with original lume intact. As a now-discerning collector, this is important to me. He also mentioned that I didn't yet have a black dial in my collection, so the 2447N fills another gap, one I didn't even realize I had! Cost: $15,000. Remaining: $10,000

Cartier Santos Carrée Ref. 2960

At this point, I realized I didn't have a modern-ish watch with a more-or-less integrated bracelet, so I decided I needed one of those. Cartier Santos it is. The sharp lines and square shape of the original Santos ref. 2960 is a favorite of mine, and since I've got the cash, I'm splurging for a rarer example with a ruby-red dial:

Cartier Santos 2960 red dial

Image: Courtesy of Subdial

It's thought these examples, with the deep red lacquer dial and matching ruby cabachon, were produced to celebrate the Santos' 75th anniversary in 1979. And this Santos is my second Cartier, so I guess you can call me a "Cartier collector" now? Cost: $8,000. Remaining: $2,000

Apple Watch Series 2
Apple Watch series 2

I'm going to let you in on a secret. I wear an Apple Watch every day I go to the gym (no, that's not every day). I got a Series 2 way back in 2016 and it still works just fine for me. Prices are hard to find, but it looks like I can snag one on eBay for 50 bucks or so, so I'll grab one of those. Cost: $50. Remaining: $1,950


Collection Conclusions

Two-thousand bucks left feels like the perfect amount to stock up on some straps, or maybe just play keno with Sarah. I've mentioned before that six feels like the perfect number of (mechanical) watches for me, and more than that feels less like "collecting" and more like hoarding — which, to be sure, the two have a line thinner than the case of my new AP QP separating them anyway.

I realize this collection is far from complete, and the reality is I'm neurotic and my tastes will change as soon as I put the final period on this article.

I ended up with a Tudor, Rolex, two Cartiers, a Heuer, and an AP. Patek is the glaring omission (still holding out for my 3970), but I suppose I can visit Sarah and try on her Ellipse if I need it. To date though, I've personally owned a handful of Rolex, Tudor, and Cartier watches similar to the ones I chose here, so I suppose this makes sense – it's nice to know that becoming $100K richer hasn't changed me much.

The only other limit I put on my collection was trying to choose one watch per brand per decade, and really choosing a watch that, to me, defines that brand and defined that decade: '50s Rolex, '60s Heuer, '70s AP, '80s and '90s Cartier (whoops), and modern Tudor.

And Now A Few Words From Our Expert Advisor Rich Fordon

After consulting Rich initially about how to build a collection with $100,000, I followed up with him for his thoughts on my final fantasy collection. Here's what he said:

We have similar taste in watches and you answered the question in a similar way to how I would've answered it, starting with something I can wear every day and then going across the spectrum of where I'd want something different after I've identified that.

My first overall criticism is with your everyday watch, the Black Bay 58: You don't always just want a value pick for your everyday watch. I might've put a little more money towards my everyday pick, maybe buying a Rolex.

We also divert in how much you spend on Cartier, but at least the Asymetrique is a great watch, from the 'expert perspective.'

The vintage Datejust was an unexpected pick, even knowing your taste a little. I might've expected a 1016 or something in 34mm, so this one was really interesting to me. It's kind of hard for a Datejust to stand out, particularly in steel, because it could look like it's from the '90s just as much as the '50s. I'd look for some details like an original roulette wheel or dial variation to make it stand out to vintage nerds like me.

I'm also in your camp that I eventually want to own a perpetual calendar, and these neo-vintage AP QPs are popping up more and more. I'm particularly interested in the rectangular-cased examples because of the references they make to early 20th-century AP designs.

Black dial watches are the most attractive to me, and you don't have a black dial outside of the 2447N, so I think this is a great pick. Perhaps more people are going to start talking about these throughout the year with the 60th anniversary of the Carrera, but regardless, it's a great watch for the money. While the Daytona is the best sport chronograph from the era, this is the best pure chronograph, because on your wrist it doesn't really wear as a sport watch.

Finally, the Santos is an interesting pick. I've been looking into this era of Cartier a lot, because there's still a some value to be found – if you're spending less than $10,000 '90s can still offer a ton of value. Personally, the Tank Americaine is a favorite of mine, but it's all a matter of personal taste and the great thing about Cartier designs is there's something for everyone.

To Rich's point, I thought about something like an Aquanaut 5066 as my daily wear instead of the Black Bay 58, but for a similar price, I just like the Asymetrique more. And if his primary other criticism is that I "spent too much on Cartier," well, that's a reality I already live with every day.