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'Let Me Grab That Bag For You': Confessions of a Bellhop

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The author, who asked to remain anonymous, worked as a doorman/bellhop at a boutique NYC hotel from 2004 until late 2006. Here now, for Hotels Week, he shares some tales.

"If I give you fifty dollars, will you go get me cigarettes?" asked the naked woman in the hotel room doorway. My answer, after picking my jaw up off the floor, was "absolutely." And not just because she was naked. It was about 2 a.m. and I was the only doorman (or bellhop) working at this chic, Manhattan boutique hotel. A pack of cigarettes meant a three-block trek to the bodega, leaving the front door abandoned. But $50 was a serious tip, especially on an overnight, and as a hotel doorman, every motion I made, every word I spoke, was fueled entirely by the desire for cash.
From the moment you check in, the hustle begins. What seems like friendly four-star service is a carefully orchestrated plan. A doorman is waiting for you to arrive and immediately grabs your bag. Before you have a chance to say, "No, I can grab this tiny, wheeled piece of luggage myself," he's already loaded it onto a cart and introduced himself during the short walk to the front desk. The bag is then handed off to the bellman, whom the doorman introduces you to and pauses just long enough for you to realize a tip is expected. The doorman may not stand there with his palm open, but he might as well. At that point the bellman has your bag(s) and you're with him through the rest of the check-in. After the awkward elevator ride, he gives you the long, unnecessary hotel room tour—"And this is the sink"—that you never needed. His time and service is worth a buck or two, right? Right.

That's the hand-off. And it happens in almost the same way at checkout. You come down to the front desk and the bellman asks to help you grab a cab. You say "yes" and he walks you to the doorman, who actually gets you the ride. It's the fastest way to double your money. The more people touch the bag, the more people get paid.

And for every obvious tactic, there are at least two moneymaking moves that you don't see. When that airport-bound bag gets walked to the curb, the guest isn't the only person that's expected to tip. Every cabbie loves an airport fare and every doorman knows it. So if we're handing them a $45 to $50 trip, we expected to be handed something in return. A cab to LaGuardia is $2 or $3. JFK is $4 or $5. Newark is a wildcard because NYC Taxi & Limousine Commission (TLC) doesn't allow the return trip. So we'd grab a cab and tell them we needed something on our end. Usually they're quick to comply, discreetly palming it to us, or throwing it in the trunk as they pretend to help with luggage. If they refused, we sent them on their way and flatly lied to the guest as to why they drove off: "That guy really didn't want to go to the airport." There were a couple times when I almost came to blows with a coworker who damn near caused a guest to miss their flight because he couldn't find a cabbie to pay up.

Beyond that little tip shakedown, most hotels have town cars lingering in the wings, waiting to be called upon. Whether it's a short ride downtown or a trip to the airport, someone at the hotel gets a kickback.

We're also good at turning a loading zone into a premium parking spot. Midday in midtown Manhattan didn't leave much parking, so we'd sell what we had, usually a spot or two costing anywhere from $20 to $50 an hour. It seems like a lot until you realize these people are paying twelve bucks for a couple ounces of Riesling at a power lunch. Those were the ways we squeezed cash. We recognized a scenario and we called the plays that we'd been taught. And if it wasn't in the playbook, we improvised. I once got a twenty for unwedging a rotten apple from underneath the driver's seat of an SUV. Ever get paid $100 to make a run to Junior's for a cheesecake? I have. If they're paying, we were always willing. Well, almost.

There were times when things got weird. I had to file a formal complaint against a guest that routinely requested the help of a bellman, only to answer the door wearing a small washcloth. One night, one of the Jackass guys paid me $20 to go buy him a battery for his vaporizer. When I brought it to his room, he grabbed me by the collar and asked, "Who the fuck stole my grass?" So, sometimes the twenty wasn't worth it.

But most celebs were low-key. There was the Law & Order star who casually walked around in underwear as I loaded luggage onto a cart. Or the Grammy winner that was constantly high and happy and tipping like she wasn't a one-hit-wonder. My favorite was the Oscar-nominated heartthrob who always tipped big, whether you helped him or not. No ego. No diva-esque demands. Just big bills and a haze of cigarette smoke. From check-in to checkout, we were required to address him with the fake name his manager provided. "Thanks, Mr. Thompson," I'd say with a smirk.

But even with the A-listers and the big spenders, the doorman gig grew into a grind. The crazy stories became pedestrian. I was there for two years. Two years of escorting hookers to guest rooms. Two years of valet-parking Maseratis. Two years of having so much under-the-table cash in my pocket that I forgot my ATM PIN. But also, two years of opening a door for a living. As much fun as I had, it's not the life I'd wish on a friend, and that's why now, when I check in to a hotel, I'm always tipping big. And you should, too.

Bellhop photo: lafotografica/Shutterstock; confidential stamp photo: Shutterstock

· All Hotels Week 2013 posts [Curbed National]