Guy’s Vegas Diaries: Act 1
By Guy Shepherd

Follow the misadventures of our man Guy. If anyone can find joy in a lost weekend, it's him.

Guy’s Vegas Diaries: Act 1


Mr. Shepherd grabs a passing tiger by the tail on a Wednesday...

and lands on his feet just in time for Monday morning.

Welcome to the tail end of a week that promises to be an epic.

I am embarking on the tail end of a week that promises to be an epic.  Palm Beach to DC, DC to New York, New York to Vegas for a UFC fight—and then a redeye run home to Palm Beach so as not to miss the Sunday celebration of my buddy J’s 60th birthday and his 30-year wedding anniversary for time happily served.   J is a man who brought to my ears the smooth-listening narcotic that is “All I Know about Girls.”

Welcome to the tail end of a week that promises to be an epic.

It’s Wednesday and wheels-up from Palm Beach to our nation’s capital.

A nice, middle-seat lady asked me “what brings you to DC?”

“I’m going to visit my—our money—at work.”

I did not have the heart to tell her it was for work.  The status of the 202 area code is not doing well among The People. All that said, work is good.  I enjoy it and do my best to bring joy to what I do.  (See my essay Douché! Let’s Keep it Clean)

I wonder if diary and diarrhea are etymologically related?

I am a fan of chance.  I met J above—a friend that I couldn’t imagine life without—in a hot tub.  If you are not a stranger-talker you are missing out on a lot.  Gladwell wrote a good book on Talking to Strangers.  However, today I’m thumbing through my Vegas diary on my iPhone.

There are more outlandish lines in my repertoire but they’re not suited for a nice lady in the middle seat:

“I’m an arms dealer” is one such line that produces quiet time.

The best worst:

“I’m going to our nation’s capital—to be there for my son. He was sexually assaulted. (Long pause.) A senior female official used her position, the way Harvey Weinstein used his casting couch….” I act like I’m an inch away from getting a little verklempt. I bite my bottom lip—which white men like to do when they’re dancing—and, then I turn my head away and remain silent.

Squirrel! When I say “Squirrel!” it’s my way of saying to myself, and to you, that I just remembered that I was trying to make a larger point but now find myself in a pleasant, what-were-we-talking-about moment.  Going forward, I’m going to collect these under the heading Guy’s Nuts.

Ah, I went back and the frame is capturing the awesomeness that are the next few days.

I’m flying American Airlines today.  (So far so good)

Pre-Pandemic, I was a default Jet Blue guy.  Once upon a time—and I hope soon again—Jet Blue crushed the 561 to 212 and 202 iron triangle. Jet Blue was—and will be again—Guy Shepherd’s hustle shuttle.

Jet Blue is currently underserving Palm Beach—which is not in my — or their — best interest.

Palm Beach is becoming the de facto capitol city of Florida.

If you follow the migratory patterns of the rich and famous— Palm Beach is it.

Jet Blue ought to serve the sucking sound that is the blue state diaspora.

In New York— the Capitol of Capital—corporations are moving headquarters and traveling down to serve a growing state whose secret sauce is how it taxes income and that it stays open.

And then there’s Palm Beach’s growing political economy.  Orange man bad—and holding court at Mar-a-Lago —is a bipartisan business import.  The army of consultants is everywhere.

Squirrel! So, like I was saying, I was flying on American Airlines from PBI and a nice, masked lady asked me if I wanted something to drink.

Of course, I say, do you have any rum?   I had two double captains-and-diet in the Palm Beach YETI cup that fits perfect in my Tumi backpack.   Sorry, no we don’t.  How about vodka?   She shakes her head. What do you have for booze?  Nothing, sir.

Ugh—how long is Covid is going to be used as an excuse? I asked myself.  Also, I had this full YETI to draw from, which violates some tenet of airline Faucism.

Before takeoff, a customer with her nose hanging over her mask was being escorted off the plane and I expect that she was being enrolled in the no-fly Karen registry.

I wouldn’t dare express displeasure to my mask representative.  Before takeoff, a customer with her nose hanging over her mask was being escorted off the plane and I expect that she was being enrolled in the registry. After this passes we have talk about a cultural reset on consumer relations.

I was particularly looking forward to restocking my YETI because during taxi and take off a young kid was screening bloody murder. When another kid joined the scream fest, I remarked to the nice lady in the middle seat that my wife and I use to call Benadryl —Jägermeister-for-kids.   Also, the moment they cease to be infants, my policy is that if I need to bribe to them in the sky to keep them from screaming bloody murder, I will give them something to scream about when we’re on the ground. Follow-through is very important. My kids have the comportment of service dogs.

I asked for a diet soda and the nice masked lady recommended a Diet Dr. Pepper.  Never tried.  Pretty tasty on its own.  Mixed with the Captain and Diet Coke that I was rocking in my YETI, it was noticeably improved.  SoCo, OJ And DDP would mix well.  Maybe a good mid-level bourbon would  be nice.   With Scotches and Bourbons—never use the good stuff in sweet drinks.

I’m going to do my best to get a handle on how the free-market of airlines is treating booze on planes. American is a no.  (Help me! Let’s crowdsource answer the rest. Send findings to [email protected]).

Guy was not a good shepherd of time on Thursday. I flew in on Wednesday for a single-table dinner salon that I was hosting at the Jefferson Hotel.  The Jefferson is such a good location for a great conversation.  The aesthetics are perfect, the staff is the best and food-and-drink play more than a supporting role.

Dinner ended at 9, as a rule, but a few of us hung around until 12 am.  After dinner, I needed some medicine before bed so I went to get some Chinese food.   As I was approaching the door to my apartment, I realized that I did not have my key.  So there I was sitting on the stoop, eating some fried rice and wonton soup—and pulling out the bad boy’s must-have app:  Hotel Tonight.

I awoke in a nice hotel around the block.  My head was cloudy but I was chilaxxed with not having to be in New York until 5:30.  I should mention that it’s my custom not to buy tickets in advance. I like to keep it open for a chance meeting.  (I’ve made 7 figures by paying retail).  Also, New York is not the joy it once was.

Jet Blue failed me again, having not got back to the pre-pandemic level of service Guy needs.   To get to NY—I would have to go through Boston. I tried valiantly to get on a 2pm Delta.  The next best was to get a 3:20 Delta flight into JFK at 4:20. As mentioned, I had a 5:30 dinner in midtown NY. Anyone who has flown in and out of  JFK knows that that the belt parkway is a parking lot of broken dreams.  Then I remembered Blade—a five-minute helicopter shuttle from JFK to 34th Street, cost: $150.   My only disappointment is that the top-shelf bar at Blades’ JFK location is not quite as hip and well-stocked as their Manhattan helipad.  Sadly, I did not stop at a bar at the airport as a hedge.  My bad.   Upon landing, I walk into Blades’ reception area and I passed the barkeep my YETI  and he filled it up with Casa Dragones tequila.  At least $50 per pour.

Having a young woman flirt with you is kind of nice.

I arrive at my dinner, comfortably late, nicely lit and in my element of human talent and liquor. A young woman visiting from LA was at the party and she took interest in the Kavorka that surrounds Guy, until a younger man with an English accent hooked up with her. I was drinking with the fellow the night before at my dinner in DC.  This man is a Kingsman.  Having a young woman flirt with you is kind of nice.  A gay buddy of mine was watching this unfold and told me that if it didn’t work out with her, that he would be there for me.  I sent him Guy’s Guide to Gays, which he enjoyed.

After a slice of 2:30 am pizza and a couple of beers to hydrate, the host of the party and I poured ourselves into a cab to crash at his apartment in Brooklyn.  At 4am I am laying on his couch, setting my alarm for 7 so I can make the flight at 7:30. I open his fridge and pour a nice cold Modello in my YETI and stumbled down his stairs and out into my Lyft.

No problem getting to or through JFK to Vegas.  Jet Blue’s hanger has a great bar.  No auto measures or the little measuring cup that couldn’t get a Gerbil buzzed.  These guys just pour and the booze line is very respectable.

Bars are very important to human happiness.  The virtue of an airport bar is it’s a safe space for morning drinking.   If Mrs. Shepherd sees me have a morning beverage at home, there is the shaking of the head.  But when we are traveling, she is there right with me — and many others — having a delicious morning beverage.   Not knowing how Jet Blue was going to comport itself, I loaded up the Yeti with two doubles of Tito’s vodka, soda and splash of grapefruit juice.  Jet Blue is not passing out booze yet, but beer and wine was available, which as a Mosaic member, Guy gets for free.

Bars are very important to human happiness.  The virtue of an airport bar is it’s a safe space for morning drinking

I landed 12 pm.  A text from my son stated that he was outside my gate. We were traveling light and walked down to the luggage area where there was an iPad with the Shepherd name on it, and off we go to the Wynn—the unofficial sponsor of Planned Man’s “what happens in Vegas, stays in Vegas” pursuits.

Our driver brings us a Rolls-Royce Phantom—whose suicide doors never get old.  My only criticism is that there was no Grey Poupon in the glovebox. The doors open and we go to the desk to pick up key cards to the players’ suite on the 52nd-floor, facing Trump International and the snowcapped desert mountains.

Waiting for us was a bottle of Johnny Walker Black and a couple of bottles of wine.   Pored a drink in the YETI—this time to the top—and my son and I went down for pre-nap lunch.

At 6pm our host. Mr. K, would be arriving and we would refreshed and ready. Act 1 over and blacked out.

Vegas Diaries— Act 2–What happens in Vegas leaves a mark

Guy’s Vegas Diary: Act III—A Hard Landing In Palm Beach