How a Local Third-Generation Barman Does New Orleans

Photos Quest Meeks / Quest Shot It

New Orleans bars are in Trey Monaghan’s blood. At one point, his grandfather, Jim Sr., ran somewhere around 30 bars in the city (you can tend to lose count after a couple of dozen). Trey’s been out there, seen what the rest of the world has to offer, but is back home in New Orleans, in the family business. Safe to say, he’s got a pretty good read on the city. We looked to him for some picks on what to do and see in the Big Easy. First, let’s get to know him a bit better, shall we?

Tell us about your connection to New Orleans and what you do there now:
Nearly 50 years ago my grandpa (Jim Monaghan Sr.) and his wife Carol started a bar called Molly’s. In his time my grandpa is credited with running or owning somewhere around 30 bars. When he died in 2001 my father took the helm. Anytime I get asked about what I do, I think about the scene in Casino where they want DeNiro to say he runs the casino. Let’s just say I oversee day to day operations of my family’s business along with co-captain a run crew called The 504th, volunteer with a couple of great nonprofits, and have a sushi restaurant with a few friends.

What’s your definition of “true adventure?”
Along with the family business, my friend Quest (the same Quest that shot these pics) and I started a podcast called “The Truest Adventure.” We define a Truest Adventure as going beyond yourself imposed boundaries. You think about how overused the phrase adventure has become and you realize quickly that the feeling of adventure comes from a certain level of risk, and stepping outside your own comfort level.

The currents will suck you away in a second, or a ship will chop you up.

An adventure you’ve had in New Orleans:
Several years ago my cousin brought her entire college water ski team (yes that’s a real thing) to New Orleans before a tournament that was happening just outside the city. We ended up in a bar that has no windows and lost track of time. We come out at first light and are pretty wrecked. What had started as a joke in the bar about going for a swim in the river quickly got real as we all decided to ditch our clothes on the exposed sandbar. As a local, you hear that this point in the river is the most dangerous stretch of water from the headwaters to the gulf. The currents will suck you away in a second, or a ship will chop you up. So my adrenaline spikes the second I dive in knowing that not only is it dangerous it’s also illegal. If NOPD catches you, they make that arrest. So we come out pretty quick all feeling like champs and smelling like the ass end of the country. It’s a couple years later and I’m lucky enough to meet Chris Ring (Retired Navy SEAL, first American to swim the entire length of the Mississippi, google him), he lets me know that those dangerous currents in that spot are a myth.

What makes for a good cocktail?
Balance. If you don’t want balance order a shot.

What’s the biggest challenge running a bar in New Orleans?
The hours. Molly’s is open 20 hours a day. It doesn’t give you a lot of time to get things cleaned up and set for open. Now add in a few more bars you have to make sure get open and that window of time keeps getting smaller. People think it’s crazy that I get to the office at 6 a.m.

Something that sounds touristy, but is actually good?
Walking Bourbon St.

I always tell first-timers that it would be like going to Vegas for the first time and not going to The Strip. You gotta do it. Best way to see the street is to start at Lafitte’s Blacksmith Shop (one of the three oldest bars in the country) with a VooDoo Daiquiri. Walk from there down Bourbon St. until you get to Conti St. On Conti is a bar called Erin Rose. In the back is Killer Poboy. Grab a whiskey grilled cheese sandwich and a Frozen Irish Coffee.

Where to Eat

Meaux Bar

The same crew that is behind Sylvain and Barrel Proof have this great restaurant on Rampart St. that has this Louisiana Gulf Fish Amandine that my girlfriend and I can’t get enough of. Go


Tons of places in the city do good local fare. Very few of them do it as a vegan restaurant. Southern Fried Poboy and a cup of their gumbo will feed the soul. This is the reason you needed to take that obligatory street car. It’s right off the Erato stop, on the St. Charles line. Go

Bywater American Bistro

Chef Nina Compton and her husband/partner Larry Miller have opened another top-tier restaurant. I’d recommend that you don’t wear your best clothes—sometimes the train cuts off the Bywater and it’s easier to just jump through. My favorites currently on the menu: Jerk Chicken Rice, Hogs Head Boudin, and Stemmed Red Snapper will give you a taste of the future of New Orleans standards. Go


You’ll feel like you’re in a Scorsese film when you’re sitting there waiting for a dozen raw oysters. They specialize in the oysters, and because of that they close down for summer break as the Gulf heats up and the oyster season closes. Go

Where to Drink

Molly’s at The Market

The people make Molly’s, from the DJ that just got done spinning on WWOZ, to the skaters, to the tourists, to the window crew. Something for everyone. And that shows in the jukebox as well. Go

The Sazerac Bar

A bunch of specialty cocktails trace their roots to New Orleans. The Sazerac would best be described as the grandfather of all of them. The bar itself can get a little stuffy so I like to ask G-Stunna to stop there when we have everyone on the bounce bus (another New Orleans staple). Go

Black Penny

Is a beer bar right on the edge of the Quarter. Some of the best bartenders in the city are working behind the bar here. If you tell them what you’re in the mood for, they will find the best beer to match the mood. This spot is right across from Congo Square, so no matter what beer you drink take it to go and step across the street to pay your respects at the birthplace of jazz. Go

Old Point Bar

Take the ferry across the river. You’ll find the best view of the city and a great neighborhood bar. You’re not going to find umbrellas in ice-cold daiquiris here. I like to keep it simple with a 7 and 7 for the warm ferry ride back across the river. Bonus, if you somehow lose track of time and miss the ferry, get another drink down the street at The Crown and Anchor. Go

What to Drink

Jim Monaghan’s Frozen Irish Coffee. Perfect when it’s hot. Perfect dessert after dinner at Meaux Bar. Better than a Bloody Mary in the morning. Mid-day drink boost. It’s everything you need it to be.

What Else to Do

You are going to eat, you are going to drink, and hear great music. That’s a given. Take some time to check out our art scene. From Ashley Longshore’s studio on Magazine St to Katie Leese in Jackson Square to BMike in the Bywater.