New Year’s Adventures at my Midtown Penthouse

You read that right. I once shared a “deeeluxe apartment in the sky” with my brother.

So what if it was technically a poorly constructed addition built across the roof of two tiny brick buildings with absolutely no heat in the winter and hallways so narrow we could never get adult-sized furniture up the stairs?

The mailbox read “PH.” It was a penthouse.

The flat was located exactly two blocks away from Times Square, Crossroads of the World, in a neighborhood dubbed Hell’s Kitchen.

Clinton — the area’s less colorful designation — was once a notorious Irish and Puerto Rican slum that slowly gentrified over the decades. The transformation dramatically picked up steam when Times Square shifted from a sleaze pit into a family-friendly tourist trap…um, attraction…in the 1990s.

The only thing “hellish” about the area these days is the traffic heading into New Jersey and the heart-stopping rents.

Of course back when I lived there, it was still a bit rough and tumble (just the way I like it) and never more so than on New Year’s Eve.

If you weren’t blessed with the opportunity to grow up in New York City I’ll let you in on a little secret: Most dyed-in-the-wool “New Yawkers” wouldn’t be caught dead in Times Square on a New Year’s Eve.

What you have in the area every 12/31 are tourists and the bridge-and-tunnel crowd freezing their asses off, acting like fools and getting blind-stinking drunk.

Not necessarily in that order.

My first New Year’s Eve at the penthouse was relatively uneventful— once we cleaned up the debris from the eight-foot copper pipe some drunken jackholes smashed through our skylight.

The next year my brother and a few of his more burly friends acted as sentries by the roof door while I toiled away at work. As I battled my way home through the revelers, I caught site of a guy in the small entranceway of our building.

I could only make out his top half since the door was one of those half-glass, half-metal jobs popular in the “iffier” areas of the Big Apple at the time.

He was bracing himself with his hands against the inner and outer doors in a half crouch, alternately looking down at the floor and staring at the ceiling. I made a quick dash toward the door thinking, “This putz is NOT gonna take a dump in my doorway.”

As I made my approach, ready to drag this slob into the gutter, an older woman, of shall we say “questionable morals” who plied her trade in the area, suddenly popped up from down below and gave me a wave and a wink through the glass.

She very casually walked out leaving mystery-man fumbling with his pants.

I’d see her work the corner of 43rd Street and Eighth Avenue most nights on my way home from work and she greeted me with her usual line.

“Honey, you are so cute, I’d do you for free.”

To which I gave my standard reply: “Coco, my heart couldn’t take it. You are too much woman for me.”


The Times Square revitalization continued unabated and as a result, the drunken year-end slobs became noticeably less shabby.

As I headed home from another late holiday shift, I was ready to party like it was 1999 (it was) and I was hoping the party my brother was hosting was still in full swing at 3 a.m. (It most DEFINITELY was.)

While the last stragglers stumbled home from the bacchanal, my brother and I made a quick garbage run to the basement where we found a guy passed out between two of the filthier pails down there.

This dude was not your run-of-the-mill wasted schmo.

He was wearing what appeared to be a $5,000 tuxedo, plus a real Rolex and gold and diamond cufflinks that probably equaled the Rosado brothers’ combined yearly salaries.

I’m proud to say we resisted the urge to roll him and, like the good Bronx boys we were, proceeded to poke him with a broom handle and yell obscenities until he woke from his slumber.

Richie Rich gave us a slight bow from the waist and stumbled out of the building. He never uttered a word.

Class and good breeding always shows.

The most memorable New Year’s Eve at the penthouse was actually the last one I spent there. The specter of massive Y2K computer meltdowns had most Americans fearing a global collapse of both the banking system and the electrical grids.

With true New York moxie,  my brother and I had a “Y2Chaos” celebration on the roof of our fabulous penthouse. The lights stayed on and our money didn’t go poof but the spectacular view of the fireworks going off directly over our heads is a memory I will carry with me forever. A real New York City moment.

I really do miss that place.  Hmmm…I wonder if I’m still cute enough to qualify for the Coco discount?