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A Cheapskate’s Guide to Collecting Rolexes

My introduction to Rolex watches came from the unparalleled fictional king of coolness, James Bond himself. By the time I viewed “Dr. No” (on VHS tape), every aspect of the film had been analyzed by the fanboy empire, including, of course, the Rolex Sub Mariner, reference 6358, worn by the movie’s star, Sean Connery.

Unlike chunky mil-porn watches that have come to dominate the adventure watch market these days; Connery’s Submariner combined toughness with just enough elegance to warrant an invitation from the battlefield to the cocktail party. Only two things held me back from immediately going out and buying one: as a teenager I simply didn’t have the cash, and even if I had, I was too cheap to pay retail.

Like most cheapskates on a quest, I gathered as much free information as I could. In the pre-Internet days that meant reading books, poring over magazines, and studying ads. My inquiries began with the Submariner and soon grew to embrace the Sea Dweller, then the GMT-Master models, the Explorers, the Milguass, Daytona and Air Kings. The more I dug, the more I realized I didn’t know.

Rolex Sea Dweller Ref. 126600

The model variants were staggering, with time itself adding to the collection, through unintentional variants like the “tropical” dials: those that have cracked and faded through exposure to the sun. For anyone on a budget, a hobby of the imagination provides the biggest bang for the buck!

I worked multiple jobs while attending the University of Wisconsin, scrimping and saving, and visiting pawnshops between Chicago and New York, on the hunt for a Rolex at a price I could justify. Prowling Manhattan one summer afternoon, I came across an older Air King in the window of New Liberty Loans. It was a stainless model, early 60s, on a leather strap. Its previous owner had committed the cardinal value damaging sin: he had it engraved.

The more I dug, the more I realized I didn’t know.

I entered the store and began the dance. Forty-five minutes of negotiating and I exited the store with a freshly polished Air King on my wrist. At 34mm, it wasn’t the size I was craving, but I didn’t care. It could have been 10mm as long as I could read the word “Rolex” on its face. At the age of nineteen I had finally tasted the dragon. I thought it was a bargain for $875, after seeing a similar model in the window of a neighboring shop for $1,200. I had remained true to my cheapskate core, holding out for the right price. The chase was now officially on.

Rolex Air King Ref. 116900


I wore the Air King through college, then my first job, gathering some Omegas along the way to keep the Rolex company. I adding to my knowledge base as we entered the Internet age. Everything I had wondered about was now becoming available with a few search parameters. Gone were the magazine and newsstand days, however my quest was still powered by shoe leather. I acquired a mid-1980s Submariner through a trade at the legendary Frum Jewelers in Chicago: a mid-sized Omega Speedmaster automatic and some cash put it into my collection.

My next acquisition came fast. Less than six months after picking up the Subby a buddy and I were celebrating our signing bonuses, he at a law firm and me at an ad agency. Two scotches into a 750 ml single malt lunch we found ourselves at the 5 South Wabash Jeweler’s Mall in Chicago. A minty early 1990s Sea-Dweller with a below-market price caught my eye. The Russians who ran the showcase told me “its previous owner felt that it was too big for his wrist.” I could care less how it wound up in their case, it was the end of the month and their rent was due. The watch was on my winder that evening and on my wrist the next day at my new job.

At the age of nineteen I had finally tasted the dragon.

By the close of the decade I found myself turning my knowledge into something useful: as a feature writer for International Wristwatch Magazine. This opened up the entire world of dealers, collecting and information gathering. Suddenly I had access. I traded words for watches, churning out nearly 100 stories and assembling a random collection. Ulysse Nardin, TAG Heuer, Panerai, Breitling, Dodane, Tudor, Omega, Doxa, Aquadive, Ball and a host of other not-so-known brands wove a stainless-steel snake through every available drawer in my office. And while I amassed better made, more expensive and vastly more complicated watches, I kept coming back to Rolexes.

Rolex Submariner Date Ref. 116610LV

Watch Guy

Several years later, at Book Expo in Chicago, I encountered author Jay McInerney (Bright Lights, Big City) and we struck up a conversation over his vintage red dialed Submariner. He called me a “watch guy.” I cringed. Did that mean I was one of those watch douchebags who posts selfies while wearing a Hublot Big Bang, driving a rented sports car and smoking a Partagas Churchill? He clarified, “you’re a watch guy’s watch guy.” That either meant I was a super-douchebag, or someone who transcended the category altogether, like Matthew McConaughey in Interstellar. I assumed for the latter.

What struck me through the conversation with McInerney was his approach to collecting. He didn’t wander around waiting for deals to come his way, he had a collecting strategy. He identified certain models and acquired them for any number of reasons: emotional, historical or aesthetic. Where I was a gatherer, he was a collector. I needed what he had, I needed a strategy and a guide.

Josh Halpern, President of Albert's Jewelers

Through a trade I acquired a blue-faced two-tone Submariner, which I wore for six months before seeing it on too many billboards, so Mr. Blue had to go. A fellow collector advised that I check out Albert’s jewelers ( www.albertsjewelers.com) in Schererville, Indiana, with the guidance that their pre-owned selection and pricing rivaled anything in Jeweler’s Row. One Friday evening found me at Albert’s, where I met my guide, Josh Halpern, president of the company.

Know your models, keep your eyes open, always be on the prowl.

Albert’s is a multi-generation family jewelry business, with Josh running the operation, and bringing his sensibilities as a veteran watch collector and dealer into the mix. Halpern expanded his flagship store to accommodate Cartier, Omega, Breitling and Montblanc boutiques, and a massive, dynamic pre-owned watch library that he turned on a regular basis. He was a watch guy, the good kind, so we talked.

Halpern provided his guidance based on a customer’s personal preferences, often referring to particular models that he had ready access to or would have to track down. He knew the brands, the models and the market. His inventory changed in waves, and patterns emerged. We began trading.

The first to go was Mr. Blue, replaced by a two-tone GMT Master with a black face. One day a series of six or seven Explorers showed up, in a range of ages and faces, all between ten and fifteen years old and well-priced.

Rolex Explorer II Ref. 216570A

Halpern explained that this particular model represented a great bargain for the collector. It wasn’t a watch you saw every day, and had the style of the Submariner with some bold style treatments. It was designed for rugged use and didn’t vary as much in price as some of the other models. It was the same watch Ian Fleming wore, to boot.

The curve

Through talking with Halpern I learned about the depreciation curve, the point at which desirable models become their most affordable before beginning to rise in value, as they are increasingly associated with the terms “vintage.”

Rolex Cosmograh Daytona Ref. 116500LN

For example, a ten-year-old two-tone Daytona could be had, at a relative bargain, where a current used ceramic bezel version commands nearly retail price. Twenty-year-old GMT Pepsi and Coke bezel watches have been going through the roof, as they enter the high end of the arc, and are expected to continue rising. Ten years ago they were half the price they command today. Through planning a ten or fifteen year collecting scheme, it’s possible to pay the least amount of money in a value curve for a successive range of models, acquiring each as they hit the low ebb.

Working with Halpern also provided access to a vast network of other collectors and sources for watches, with an intermediary to examine and warranty the purchase. With guidance I’ve put together a short list of models that have always intrigued me and will form the basis of a calculated collection, based on the ebb and flow of the market. Of course, with a steady influx of new product, there’s always the chance that a random bargain will come through the door, something worthy of trading for. But that’s part of the fun of the game.

So what’s the biggest takeaway about being a cheapskate Rolex collector? Find someone you can work with and trust, who has forgotten more than you will ever know. Anything after that is luck. Know your models, keep your eyes open, always be on the prowl and, above all, remember: Full retail is for rubes.

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