Timepiece Crime and Traveling with Watches, Africa Watch Loadout, Part II

Timepiece Crime and Traveling with Watches, Africa Watch Loadout, Part II

In this week's Dispatch, we continue our exploration of the massive uptick in watch-related crime and discuss traveling with watches. 

Africa Watch Loadout- Traveling with Watches

See Part I, Criminal Rolex Gangs and Traveling with Watches

In early 2022 I planned a return trip to Africa–a continent where I’ve spent much of my life and a place where I feel at home. Like most things in the life of a former CIA Case Officer, it was to be part pleasure, part work: a mix of business meetings, reconnecting with old friends and some time on safari in the bush. I planned to spend most of the trip in rural areas that were deemed safe by most standards, but would travel through Johannesburg and Nairobi–two cities notorious for petty crime that can sometimes turn violent. 

My view is that a relationship can be developed with seemingly inanimate objects through shared experience, and this particularly applies to watches. It wasn’t a question of if I would bring a watch, but which watches I was going to bring. This might seem risky because “Africa is dangerous.”  Despite the ignorance of generalizing a continent of 54 diverse countries, there is some truth to this statement. As we explored in Part I, watch-related crime has skyrocketed globally over the past few years and traveling anywhere with a luxury watch requires certain considerations. That said, I believe many parts of Africa are safer for watch aficionados than London, New York or Paris.

Decades from now when I’m telling my grandchildren stories about my watch collection, I would rather tell them that their grandfather’s watch was stolen at a bar in Maputo instead of admitting that the watch sat in a safe for 30 years and remains in pristine condition. Watches are tools. I am willing to risk the potential loss or damage to use them for their intended purpose.

Watches of Espionage W.O.E.’s Personal Rolex GMT 16710W.O.E.’s Personal Rolex GMT 16710, Photo James Rupley

Rolex GMT- The Case Officer’s Watch:

Had it been 2019, I would have brought my Rolex GMT-Master II, an early 2000s black and red “Coke” ref 16710. For years, I have said that the Rolex GMT, any reference,  is the ultimate CIA Case Officer’s watch– a classy and refined tool that signals to others you are a man of culture, yet don’t mind getting your hands dirty. The ideal Case Officer has been described as a “Ph.D. that can win a bar fight,” and I have always envisioned this persona wearing a Rolex GMT.  (Full disclosure, I don't have a Ph.D, and during my last bar fight–which was more than a few years ago–I was likely wearing a Breitling.)

When hopping time zones, the quick-change date and GMT functionality are useful for confirming the time back home, and a simple wrist check is easier than pulling out a phone. The watch also captures the nostalgia of the romanticized vision of the Rolex GMT, originally developed in the 1950s for commercial Pan Am pilots. While all my watches are insured, I still questioned the wisdom of traveling to Africa with a watch worth significantly over $10,000 and engineered by one of the world’s most well-known brands, Montres Rolex SA.

I’ve heard that one of the tests for Rolex models is that all designs must be recognizable from 20 feet away. While I am not privy to Rolex internal company practices, this feature seems to be accurate in the real world. A semi-trained eye can recognize a Rolex from across the room in a dimly lit bar, and thanks to social media (See Part I), in 2022, semi-trained eyes are all over the place. A criminal call out scanning the arrivals hall at Nairobi Jomo Kenyatta International Airport could do the same, immediately pegging the Rolex wearer as a potential target. 

Sure, in an emergency, I could potentially trade the Rolex for a plane ticket, ride to the airport or facilitate a border crossing, but at a certain point the watch is more likely to get you in a bad situation than out of one.  It is a liability, not an asset.  The Rolex was out.

Affordable Watches:

The logical decision–the “school solution”-- was to travel with one watch, something that would not draw attention and be durable enough to make it through any expected or unexpected adventure. It needed to be waterproof to a certain extent so that I would not have to take it off for a dip in the ocean or hotel pool, something that I could keep on my body at all times. An automatic movement mitigated the possibility of battery failure–something that always seems to happen at the worst time, i.e. day 2 of a 3 week trip. It had to be replaceable, from both a monetary standpoint but also from a sentimental point of view. Insurance solved the former, but the latter ruled out some watches that could not be replaced, such as a Jordanian Breitling Aerospace–a gift from the King of Jordan.

Watches of Espionage - Affordable SeikoAffordable Seiko, Photo James Rupley

Something like a sub-$500 Seiko 5 Sports would satisfy these requirements and provide a great travel companion for any scenario. That said, I wanted to step it up a notch and bring a couple of unique pieces for my journey. 

The Decision:

I posted the following picture on Instagram @watchesofespionage and solicited W.O.E.’s (then) 60,000 followers for advice. 462 comments contained everything from “Bring the Rolex” to “Leave them at home and wear a Casio.” These comments were indicative of the scenario: the correct answer is, “It depends.”

Watches of Espionage - Africa Travel

In reality, I had already returned from Africa when I posted this pic. If you think a former Spook turned watch influencer posts his travel plans in advance, you’re smoking crack.

The Load Out:  

Ultimately, I decided to travel with two watches, one “formal” watch that could be worn with a suit and one “informal” watch for adventures in the bush– something perishable and under $1,000.

Tudor Black Bay 58 in its element; sundowners in the bush.
Tudor Black Bay 58 in its element; sundowners in the bush, Botswana.

Black Bay 58:  As a big proponent of Tudor, I believe The Shield produces the best modern luxury tool watches. I quickly decided that the Black Bay 58 (BB58) would make a great travel companion. It was in. The watch had traveled with me to a few countries but was still relatively new and I had no real emotional ties to it. A classic steel sports watch, it was tough and had many of the benefits of a Rolex but without any of the drawbacks, and could be easily replaced for under retail price if needed. The BB58 is a relatively simple watch and an homage to the Tudor Submariners of the 1960s, which had been worn by Special Operations units both in the United States and abroad.

CWC SBS Toyota Landcruiser - Watches of Espionage
Two tools, CWC SBS and Toyota Landcruiser.

CWC SBS: I had recently acquired a Cabot Watch Company (CWC) SBS with a Tritium Dial from the late 1990s. The SBS was originally developed for the British Special Boat Service (SBS) in the late 1980s and is still issued to select British units today.  The watch was designed to military specifications, with a quartz movement and day/date feature. As a bonus, unless you are a “watch-guy,” the CWC is unremarkable and unlikely to stand out in a local market or hotel lobby. 

It was unnecessary to bring two watches on the trip but they complemented each other well. I found myself wearing the (more affordable) CWC and the day/date feature was generally useful for everything from filling out customs forms to reminding myself the day of the week in the time warp that is African bush. The CWC has fixed spring bars, so I brought several straps along and changed them out frequently and with ease. The Tudor–one of my favorite watches– paired nicely with the CWC, but with no date or GMT feature, it was less practical as a travel watch. 

Brodinkee and Watches of EspionageOriginal Brodinkee Meme making fun of W.O.E.

I can already visualize the “first world problem” @Brodinkee memes about the difficulty concerning the decision of what luxury watches to bring to the developing world. But for someone who is truly passionate about timepieces as a hobby, this is what collecting is all about. Shared experiences with these inanimate objects are what brings them to life. When I left for Africa, these pieces had little to no sentimental value.  

But now, as I reflect on these tools, I remember wiping the dust off the crystal of the CWC as I scanned the sky for the Cessna Caravan that was late to the remote dirt airstrip, standing on the edge of Victoria Falls with mist drenching the Tudor dive watch and striking up a conversation at the hotel bar with a former British military officer that started with “Is that a CWC?”

I never felt unsafe or targeted for wearing a watch, and in hindsight, I could have brought my Rolex GMT; it would not have been an issue. In fact, traveling to parts of Africa with a luxury watch is likely safer than walking the streets of London, Miami or Barcelona. That said, there were a couple of times that I pulled down my sleeve to cover the watch, and once or twice, I took it off and put it in my front right pocket with my passport and wallet. 

Overall, the trip was a success and my watch choices proved to be perfect.  The watches are tools, like my Emerson knife, Swarovski binoculars, or Palladium boots. They are an extension of my persona, and had one been stolen, misplaced or damaged, I would have recovered. The risk/reward balance was there. 

I did find myself needing a better travel case, which ultimately resulted in the creation of the W.O.E. Travel Pouch.

EDC Africa Watches of EspionageA few other necessities for travel to Africa.

Looking back at my selection, I would have appreciated having a GMT feature on either the Tudor or CWC.  Tudor makes a Black Bay Pro that would have satisfied this requirement and there are a number of sub-$1,000 GMTs on the market, including a new Seiko 5 Sports GMT for $475.

I guess it's time to buy another watch.



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Read Part I, Criminal Rolex Gangs and Traveling with Watches

Watches of Espionage - Tudor Black Bay 58

This newsletter has been reviewed by the CIA’s Prepublication Classification Review Board to prevent the disclosure of classified information.


@rich thomas – great comment. I work in Uganda and am often checking I’m not being overt with wealthy objects (I’m far from rich, by western standards, but by Ugandan, more than better off than most).

I even go as far as to not clean my running shoes so as to not look too good when running with my local friends. (Though I do take good care of them so they last..).

Its about decency and emotional intelligence of your surroundings and friends, I think.

Walton Hemingway

Love your content! As a proud owner of a Coke GMT, I echo your comments.

My current travel watch is a Tudor Pelagos 39 on a rubber strap. It is my favourite in the modern catalogue (even over the Black Bay) and I’ve grown to love it so much it now what I wear every weekend and a lot of days in between as well.

Tudor is what Rolex was.

Scott G

I did a business trip to London and Amsterdam this past fall, and had the same internal discussion. The Rolexes stayed home in the safe. I brought the ‘modern’ black bay Pro GMT you mentioned as the ‘dress’ watch (always with a sleeve) and the cool G-Shock GA-B001SF-7AJF for ‘street’. No issues at all, other than trying to get INTO a watch shop in central London, asked to remove my hat and sunglasses (too incognito apparently). P.S.: Recently picked up an inexpensive quartz Dunhill Dunhillion 8033 chrono, which has GMT functionality, may go into the rotation! (Enjoy your content!)

George C

For a special birthday in 1978 I ordered a Rolex day-date in gold (later known as the President’s Watch). It was gaudy and I foolishly wore it on vacation to Jamaica. In a market I was offered heroin! It was due to the watch. On return to the US I was taken in a small private room at O’hare where I was searched. I decided to never wear it again and I sold it. Since then, I am very careful both here in the US and outside to wear only plain vanilla watches like my Seiko Mod, which I love anyway. I do not need to show off. I feel secure in my own self and I have no need to impress anyone. Of course, I am older and hopefully wiser too.


What shirt and sunglasses are those? They’re great.

As for a watch, my Breitling Emergency is my GADA watch. It ever leaves my wrist and I don’t plan on it going anywhere unless some machete-weilding moped riders chop off my arm.

Great write up!


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