March 03, 2009


By Paul McGuire © 2009

Monroe sat at the end of the bar on the last stool. He always did. He never left. The octogenarian arrived five minutes before O'Looney's opened and had to be carried out every night when one of his grandkids stopped by to pick him up. I always wondered what Monroe did in the time he left the bar and the time he arrived. He was habitually cranky, a terrible tipper, and rarely said a word unless it was to complain about the Red Sox. Even when they won, he never had a positive thing to say about those "overpaid queers who needed a shave."

What did that fucker do when he wasn't at O'Looney's?

I assumed that he passed out. Pissed himself in the middle of the night. Woke up in a pool of cold urine. Showered, and then waited for O'Looney's to open so he could repeat the process.

I told most of my friends about my fascination with Monroe's non-bar life. They thought I was losing it and refused to listen to me pontificate about Monroe. They all hated O'Looney's and everything associated with it. They always wondered why I worked there.

"It's an old man's bar," they said. "There's one in every town you're stuck in the worst one in Connecticut."

They were bitter because O'Looney's always carded them when we were in high school and college. Their grudges clouded their judgment, but the balls-to-the-wall truth was in the tip jar. I pulled in more than $100 in tips on one day a year... St. Patrick's Day... and that was it. The regulars? Those old guys didn't tip well. Some of the guys, like Jimmy Moran's father, ordered whiskey and soda which cost $4.50. Pints of Budweiser cost $3.50. I was lucky if they let me keep fifty cents. Some of them, like Monroe, only tipped a quarter when I gave them their change. I'm getting twenty-five freakin' cents to pour a pint, and it wasn't like they drank five or six in an hour. They nursed an entire pint for hours until it became warm piss.

My tips would increase substantially if the bar allowed underaged kids to drink and looked the other way every once in a while. And I wasn't talking about turning O'Looney's into a full on kiddie bar, but on numerous times I proposed that we should relax the stringent "check everyone's ID who looks under 30" policy for just one evening a week. Just think about how much more money that could have generated for till? And my tip jar could actually approach triple digits!

Alas, management wasn't going to even consider that prospect, and management was the surly and heavily intoxicated Kevin O'Looney, the son of the Shamus O'Looney, most known around New England as the barkeep who served drinks to Teddy Kennedy on the ill-fated night of the Chappaquiddick accident.

Location was always important in any sort of business. At the time Shamus O'Looney opened the bar, O'Looney's was strategically placed near an old shoelace factory. The bar was packed twice a day when the night shift ended at 6am and when the day shift ended at 6pm. On the weekends, it was a popular hangout. My father and my mother's cousins frequently drank there on Saturday nights.

The factory shut down in the late 1979 and it was demolished in the 1985 when a developer decided to build condos. O'Looney's lost their daily blue collared working class binge drinkers. A few regulars continued to drink there out of loyalty, but as they got older, the bar attracted less and less customers.

If O'Looney's was located closer to the train station, then they'd be overwhelmed with a hipper clientele. It was up on the hill instead, so the bar lacked an influx of thirsty commuters returning from the City. The lawyer and Wall Street rich-guy types attracted the gold diggers and the local college girls. Instead of hanging out inside the dirty booths at O'Looney's, they all drank and ate at Mulligans or The Glass Onion. If you saw a female under 40 years old at O'Looney's, you had to figure that she was lost, looking for change for the parking meter, or a prostitute.

One girlfriend broke up with me because I worked at O'Looney's. Becky Cohen. Man, she was a piece of work. Sure, she was great in the sack and we had some fun times together, but she was way too concerned with her image. And that included who she dated. She couldn't brag to her friends that I was a stock trader in Stamford or some hotshot attorney working in the City. She actually told me that she was embarrassed that I worked as a lowly bartender in an old man's bar. Becky often encouraged me to go back to school or look for jobs in the City. I told her that I didn't want to have to commute and living in the City was ridiculously expensive. I'd be spending 90% of my tips on renting a roach-infested shoebox in the hood.

When I wouldn't quit O'Looney's, she quit on me. Heartless cunt. She got what she deserved. Although she married a hedge fund manager and moved to Westport, a tinge of karma fell my way when I discovered that her husband lost millions in the Bernie Madoff ponzi scheme.

O'Looney's and I had a unique relationship. It was an integral part of some of my most favorite childhood memories. During my first year in Little League, we were sponsored by Angelo's Pizza. The owner gave us free pizza when we won our games. His pizzeria was located on the same block as O'Looney's. I loved it when my parents drove by O'Looney's after dark when the different neon colored beer signs were lit up in the windows. Those series of odd colors from the fuzzy illumination of the neon were nothing like the shades that I found in my 64 pack of Crayolas. That's when I developed a fascination for neon beer signs which would eventually get me in trouble when I was 21 years-old and a part-time student at Central Connecticut College.

One random evening, I drank an entire bottle of Jagermeister with a couple of friends of mine. We stumbled into the local bar and consumed endless rounds of Goldschlager shots with a gaggle of hot sorority girls. At that point, I blacked out. During that lapse in both memory and judgment, I pushed through the crowd and grabbed one of the neon Bud Light signs off the wall. I marched out of the bar with the neon sign under my arm and flipped off the bartender on the way out. I went back to my apartment and hung it up on the wall before I passed out on my couch.

A knock on the front door woke me up the next morning. It was the campus police. I quickly apologized for my drunkenness and offered to bring the sign back personally. The cop drove me down to the bar and the owner of the bar chewed me out for twenty minutes.

After his rant about the decline of the work ethic of young Americans, he offered me a job as a bar back. The job didn't pay much and it sucked watching all of your friends around you get shitfaced when you had to work. However, I realized that the job was a perfect front to deal drugs. I dropped out of school that semester and sold weed and ecstasy in the alleyway. My clients met me next to the dumpster. It was a perfect cover because I frequently had to go outside to throw out trash.

When the owner found out that I was dealing, he wanted a cut. If not, he was going to rat me out, so I immediately quit. I was out of work and dropped out of school. I bummed around a bit as a plumber's assistant. The hours sucked but the pay was pretty good. The plumber that I worked with used to stop at O'Looney's every night on his way back to the shop. That's when I starting drinking there regularly. Shamus O'Looney remembered my father and my uncles, so he offered me a job bartending at O'Looney's. I quickly quit my job in the plumbing business. That was almost ten years ago.

I met a marijuana grower from Vermont through a mutual friend of ours. We frequently played poker together at Foxwoods and he told me that he was looking for someone to help him unload some product. I expected to meet an hicky farmer type who looked like Greg Allman or a young hippie kid with dreadlocks. My assumptions were wrong. The grower, Mr. Blue, looked like an investment banker. Short hair. Clean cut. Fresh cologne. Black Berry. He always wore a nice suit (minus the tie) and drove a Mercedes. He practiced the art of deception perfectly and loaned me several philosophy books by Sun Tzu and Machiavelli. He was the last guy you'd pull over for suspicion of drug trafficking.

Mr. Blue dropped off a couple of pounds every few months and the next thing I knew, I was back to dealing. Except, it was on a much larger scale. No more dime bags out the side door. The bar's location was the perfect front for me to deal. O'Looney's was such a boring place that nothing ever happened there. The cops left us alone because they knew we did not serve underaged kids and that none of the old guys ever got into fistfights. Maybe once a year, we had to call the paramedics because one of the customers had a heart attack or stroke, but that was it.

Most of the time, Monroe just stared off into space or watched the TV above the bar. The old guys preferred watching CNN during the daylight hours. As soon as it turned to dusk, I flipped over to NESN or wherever the Sox were playing. While they argued about sports and politics, I conducted business right under their noses. The old farts had no clue what was up. Random pothead friends met me in the parking lot behind in the back. We'd smoke a joint and complete the transactions. A couple of the delivery guys who worked at Angelo's were my biggest customers. They often gave me free pizza and meatball sandwiches in exchange for quarter ounces.

Shamus O'Looney had been dead for two years and Kevin was completely out of the loop, but I always suspected that Monroe knew a lot more than he was letting on. He often sneered at me after I returned from completing a deal outside, like he knew that I just sold weed on the side to supplement my income. I guess that's why he only tipped me twenty-five cents sometimes. Why tip a drug dealer?

Paul McGuire is a writer originally from New York City and currently residing in Los Angeles, CA.

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