My Hunt for the Italian Hustler

How do we tell apart a good and a bad choice without knowing the outcome of both?

I try to be at the gym at 2:30 p. m., every day, give or take half an hour— before it gets filled beyond capacity. Friday, however, I decided to break the routine, and that made all the difference.

After I left my house, I took out the trash, used the back exit of the neighborhood and arrived at the gym’s parking at 1:30 p. m. As I drove to the far end of the parking, I came across the usual stop sign that sits at one of the entrances. The first car that pulled in was a gleaming, black Jaguar with a young man inside. “How the hell did this kid get that car?” I thought. He pulled up next to me, and signaled to roll down my window.

“Do you speak spanish?” he asked, in an awkward spanish accent.

“Yes,” I said.

“I’m lost, how can I get to the airport?”

I noticed the line of cars stacking up behind him.

“Let’s pull up and talk,” he said.

The man wasn’t as young as I thought he was—late twenties or perhaps lucky thirties.

“I’m trying to find the airport and I don’t know which way to go”

I explained to him as best as I could while wondering how he could own the car but not a GPS. When I finished, ready to go on about my day, he told me to wait.

“I work for Emporio Armani,” he began, “and just left a conference where we made a deal with JCPenney. Come—come to my car, I want to show you some merchandise.”

I looked around, suspicious of this man’s intentions, but got off my car regardless.

“The company paid for this car?” I asked.

“No, I rented it,” he showed me the rental papers. “Come sit.”

“I’m fine here.”

“Where are you from?” he asked, with a grin.

“Colombia.”

“Oh! My girlfriend is from there.”

He grabbed three Emporio Armani bags from his back seat, each with small, black boxes inside.

“I’m from Italy,” he said. “I have to be at the airport at four so I can fly back.” He had eleven watches. “If I take these watches with me I’m gonna have to pay 32 percent tax once I get to my country.”

He pulled out his phone—a Galaxy S4—and showed me the price of each watch in the company’s website (ea-urology.com). The cheapest watch he had cost $660; the most expensive one neared $13,000. He grabbed a lighter and, with the metal part, began to hit the glass of one of the watches. “It’s sapphire—it doesn’t scratch,” he said. Then he lit the lighter and placed the flame against the band. “Look, it doesn’t burn. Even this plastic-looking band—doesn’t burn. Touch it, it’s warm.”

He handed me the watch to examine its legitimacy as he hit and burned a few more. The underside, with its transparent case back, revealed the inside of the self-winding watch, where I noticed the words “Orologio Moda Italia.” “What can you give me for these?” he asked. “Give me $500 and they’re all yours—eleven of them.”

As I thought about the great offer and a way to get the money, the vision of the 6 o’clock news coverage of the incident overlapped my optimism. I could imagine the news anchor’s announcement: “young man is robbed after an attempt to buy $10,000 worth of stolen merchandise for $500. The cops are looking for a man with an awkward accent.”

“I don’t have the money with me,” I said, making an I-wish-I-had-it, sorry-I-don’t expression.

“Do you have it at home? I can follow you. Brother, I have to be at the airport.”

“I don’t have cash at home. Let me make a call, I know someone who’ll be interested.”

“No no no—hang up, I don’t have enough time.”

I did not thoroughly examine the eleven watches, but the ones I did appeared as real as they come. Besides, if his fire show, the strong smell of leather and the smooth, oscillating movement inside the watches was not enough, I didn’t know what else to look for.

“What type of phone is that?” he asked after I hung up.

“An iPhone 5.”

“Let me see it, my sister wants one of those.”

I didn’t hand it to him.

“You have to understand my skepticism,” I said. “You’re gonna lose a lot of money by just giving me those watches for so cheap.”

“I’m not losing anything,” he said. “They were given to me. If I take them to my country I have to pay about $2,000 in taxes. I don’t want to pay that much money just so I can give them away to my family.”

I made another call. When my friend answered I gave him a quick recap of the situation. “Do you have $300 cash?” I asked.

“I need at least $800, man. This is a lot of stuff” the man interrupted. “Trade me your phone. My sister wants an iPhone because she says the Galaxy is too bulky.” He pulled out a brand new Galaxy Note II and turned it on. “Look, I’ll give you this phone and the watches, just trade me your phone.”

For some reason, trading my phone seemed murkier than getting the money. When I offered to instead call someone who could meet him at the airport and buy his watches, he refused, said it was a pleasure to meet me and parted.

I called back my friend and told him the whole story. I told him about my certainty that the watches were real, about the Italian’s back story and the many reasons I didn’t give in to his offers. But as I spoke, a feeling of regret began to creep into my mind, intensifying with every word. Reasonable choices seemed like excuses, labored and lame, that kept me from benefiting from an otherwise timely stroke of luck. Could I have negotiated differently? What if the watches were fake? Was it stupid not to take the deal? I called back my friend—“let’s go look for him.”

My friend and I were about 15 minutes behind, under the assumption that the man’s story was true, that he was lost and followed my directions. The same street that led him to the gym is the same street that would lead him to the airport, but in between there are many marketplaces and shopping centers. If he’s trying to get rid of those watches, I thought, he might stop by one of the parking lots. The plan was to find the car, tell him “never mind” and negotiate.

After looking around the area with no luck, we debated whether going to the airport was a good idea. We looked up the phone numbers for car rentals at the airport hoping to figure out which one rented Jaguars. The task was arduous; we agreed it was a bad idea, that we wouldn’t find him there. At 4 p.m., ignoring the man’s story, we drove to other areas of the city. I don’t know what we were thinking at this point, but I know we didn’t want to give up our optimism.

We drove for three hours before coming home. We visited a total of eight different places, including parking lots, malls and even a Jaguar dealership. At one point we chased an Infinity before catching up to bitter disappointment.

I told this story to five different people and all of them had differing comments. One assured me he was a “scam artist,” but I argued he could have made a lot more money by individually selling each watch; someone else said perhaps he was working with or was watched by the police; the friend with whom I rode said perhaps he was so rich he didn’t want to go through the trouble of paying taxes and selling the watches, and instead wanted quick cash; someone expanded on the idea that it was, indeed, too “weird” to understand; the most compelling comment argued that, even if they were fake, each watch could have been sold for at least 100 dollars.

I didn’t verify whether his 32 percent claim was correct, nor do I want to—many details of his story were inconsistent. Part of me regrets not finding a way to make a deal with the man, but I believe I was right with the majority of my decisions. Looking for him around the city went over the top, but I was satisfied to let my curiosity pursue the answers speculation will never obtain. I should’ve just asked for the one logical thing at the time: his passport.