The Starboard's Monty talks crushes, celebs after 20 years of ownership in Dewey Beach

On any given night, ESPN SportsCenter host Scott Van Pelt might very well drop a reference to one of Delaware's most famed watering holes, The Starboard, or its co-owner and public face, Steve "Monty" Montgomery.

Van Pelt, who grew up in the Washington, D.C.-area and has been visiting Dewey since he was a kid, is a regular visitor to the bar that made the Orange Crush so popular that it could be the state drink.

Whether you're a local, a weekend warrior or a well-known television personality, it's easy to be drawn into the cult of The Starboard — a Dewey Beach world of Montgomery's creation.

He's the man responsible for thousands of hangovers and they love him for it.

Montgomery's Starboard is a place where it is not uncommon for people to stay longer than an average work shift, happy to not only pay the ensuing bar tabs, but also post them on social media to brag about their Starboard fandom.

It wasn't always like that. That's all Monty.

Montgomery, who celebrates his 20th anniversary this year, has turned what was once a small beachside Italian restaurant into a constantly evolving behemoth of a bar with yearly upgrades that keep his diverse mix of customers coming back.

At The Starboard, no one even flinches at the sight of a man born in the 1930s slamming a shot with recent college grads in the hodgepodge bar that sits on Del. 1 along the same strip of roadway as other go-to bars such as the Bottle & Cork and The Rusty Rudder.

And that is part of The Starboard's secret. While other bars in Dewey Beach heavily target customers in their 20s, The Starboard draws all ages at almost all hours. That's how Montgomery and his bar first got their hook in ESPN's Van Pelt and why he comes back.

"For us, now that our Dewey glory days are decades in the rearview mirror, the beauty of The Starboard is that we can find a spot there where we’re still very welcome and we’re not in anyone’s way," said Van Pelt, 51, who has his own sandwich on the menu: The Scott Van Melt. "Our time has passed, but there’s a bit of an element of time standing still there."

As former Starboard owner Chip Hearn puts it, "Monty knows the D.C. crowd, the Wilmington crowd, the Baltimore crowd and the locals. What other place in Dewey has that mixture? Every place in Dewey has a following, but Monty is the only one who has all followings."

Van Pelt isn't the only famous face that knows the way around the shark-themed bar. 

Everyone from Sandra Bullock and Denzel Washington to Luke Wilson and BET founder Robert Johnson have tipped one back at The Starboard.

"Sandra is one of my sister's very best friends. She used to change my diapers, for God's sake," Montgomery says of his one-time babysitter.

Like Walt Disney, but with alcohol

Montgomery and partners Dick Heidenberger and Jim Weisgerber, owners of The Bottom Line in Washington, D.C., at the time, bought The Starboard from Hearn and his family in 1999 after they had owned it for 13 years.

Others wanted it, but Hearn knew Montgomery and his zeal for the bar. When Montgomery rounded up his partners, it was his.

Since then, long lines have been forming, a seemingly endless number of oranges have been squeezed for crushes and Montgomery has morphed from a bar owner into something closer to a mascot.

"When you sell a place that gets better, that's the greatest thing that can happen. You feel good," says Hearn, 65, who marvels at what Montgomery has done to his old haunt. "It makes you go, 'Yeah, my legacy is secure,' while they just keep improving."

Whether he's in his bar or out in the community, Montgomery is an instantly recognizable face for the thousands who flood his bar each year.

When there's a line on a hot summer night, you'll invariably hear someone tell the doorman that they know Monty. Everyone does, so it doesn't work. So much so that it's a joke — one that has even landed on official Starboard merchandise.

"When he leaves for work, I tell him have fun shaking hands and kissing babies. He really knows how to market himself really well," said Dee Dee, his wife of 14 years. "I'm always known as Monty's wife. I sometimes wonder if people know I even have a name."

Even though he seems to revel in it, Montgomery says he would actually rather be in the background.

"I hate being in the spotlight. If I could have two-way mirrors and just watch people have fun and make sure everyone is having a great time, I'm happy," he said.

Creating a festive wonderland and watching people leave politics at home and let their hair down is what Montgomery says drives him. He's like Walt Disney, but with alcohol.   

When the Montgomerys were married at the Rehoboth Beach Country Club, their wedding night ended at The Starboard, with their wedding party in tow. They really had no choice. For a man some call the unofficial mayor of Dewey Beach, his customers demanded an appearance.

"We went there because people wanted to see us — just our regular customers. It was crazy — there were so many people there," Dee Dee remembers. 

He's so popular in his bar that if he did a shot with every customer who bought him one, he'd be falling down drunk nightly. He's perfected the art of the phantom shot, either doing a shot of water or pretending to drink when everyone else's heads are tipped back.

The couple live with their two children, Savannah, 11, and Brooklyn, 7, in a quiet neighborhood just outside town tucked away near Rehoboth Bay. A five-minute drive takes Montgomery from his high-octane party scene to his tranquil home with a pool out back and a sports-themed man cave in the basement complete with a full bar and wine cellar.

In addition to The Starboard, Montgomery is a part owner of Dewey's Starboard Raw,  Bethany Blues restaurants in Bethany Beach and near Rehoboth, the waterfront restaurant at Bethany Beach Ocean Suites named 99 Sea Level and Rehoboth-based Atlantic Transportation Services.

He is also a partner in the ownership group with Nick's Fish House in Baltimore with Under Armour CEO Kevin Plank and others.

And, yes, he has heard requests for a Starboard in other towns, but he refuses. It just could never be the same and he doesn't care to try the experiment. He's worked too hard to build up the brand to sully it. 

"I laugh when I hear it," said Montgomery, who turns 50 next month. "The Starboard is what it is because of Dewey Beach."

Fun is the priority

Montgomery's parents were living in Arlington, Virginia, when he was born, and his grandparents owned one of the original houses in Henlopen Acres, just north of Rehoboth Beach.

At only six days old, Montgomery first visited Dewey — a town where he has been working ever since, starting with renting umbrellas on the beach for Catts Beach Service as a teen.

It's those roots that give him an advantage — a keen feel for the town and its people, whether they live there or are regular visitors. 

As Hearn puts it, "You know how they say if you play for the Los Angeles Dodgers, you have Dodger blue blood? Well, Monty has Dewey Beach blood. I know it sounds silly, but it's not." 

Back when Montgomery was working the beaches, the rental umbrellas were used not to keep sun off the skin of co-eds, but to keep kegs cool.

That was before drinking alcohol on the beach was banned in 1986, eliminating Dewey as one of the last East Coast beaches that allowed open containers. All those people in group houses would rage on the beach, not the bars.

Montgomery was 18 in the summer of the beach alcohol ban, just starting at The Starboard as a doorman. Little did he know the implications of the ban. Once Dewey's party crowd couldn't drink on the beach, they came inside, igniting the town's now-notorious bar scene. 

The timing couldn't have been better for Montgomery to start working his marketing magic. When he took over, Dewey was in full swing.

The Starboard had been a Bloody Mary bar and still features a fierce Bloody Mary bar on Sundays, but once Montgomery brought the Orange Crush north from West Ocean City about 15 years ago, everything changed.

The 16-ounce, $8.50 drink with a heavy pour and squeezed-in-front-of-you juice has become the holy grail of cocktails in Dewey — a far cry from the buckets of Rolling Rock bottles that one dominated The Starboard back in the day.

The Starboard's Orange and Ruby Red Grapefruit crushes account for 60 percent of all alcohol sales, Montgomery said. Their crush menu now offers eight different varieties including watermelon, lemon, tequila, mango and more.

The drink, as well as the show of making it, is so important that Montgomery only lets his bartenders pre-squeeze juice on two weekends each year: Memorial Day weekend and the weekend of their Running of the Bull event in July.

He also decided to combat lines by offering VIP cards to the bar's loyal customers, giving them a separate entrance and a better shot of getting in than a random first-timer.

The bar's Running of the Bull is an event brainstormed by Starboard regulars more than 21 years ago. It's a brilliant reflection of the sometimes goofy nature of the bar: Two people in a bull costume run across the beach before returning to the bar for a "bullfight." 

All the changes have resulted in a bar that draws thousands to its opening weekend in the middle of March to a 19-block-long speck of a beach town. It's so big that they erect a giant tent over the parking lot to contain the bash.

The Starboard's fandom can be measured by the number of Starboard bumper stickers, hats and T-shirts you can see not only in Delaware or the region, but across the country. In fact, after the Montgomerys got off their plane in the Bahamas for their honeymoon, they spotted the pilot disembarking with a Starboard hat atop his head.

Over the years, Montgomery has built a staff that is more like family with employees often coming over to his home to watch football games or going on getaway trips. That's the same vibe his staff gives off to their customers, making the bar as comfortable as a living room.

Keith "Toastie" Kirk began working at The Starboard at 14, spending two summers making toast for the bar's big breakfast and brunch crowds.

Mirroring Montgomery's own ascent from a teenage entry-level position, Kirk, 34, is now The Starboard's general manager and finds himself giving the same direction to new employees as Montgomery gives others. It's all about fun.

While Montgomery wants sales just like any business person — his have grown in all of his 20 years as owner and are now six times what they were in 1999 — the experience getting there better be fun or it isn't worth it, Kirk says.

In fact, Montgomery shuts down his bar on the third Monday of July while summer is in full swing to host a staff party at Fager's Island in Ocean City with three busloads of employees. It began after he noticed through the years that his staff usually hit a wall after working nearly nonstop for months, and the fun faltered.

Instead of ordering them to suck it up, he decided to throw a party. The result? His staff blows off some steam and is back the next day ready to crush the rest of the summer.

"Everyone is at their wit's end so we go home, put nice clothes on and have a couple of cocktails — six, seven, eight, nine 10 of those," Kirk said. "It's a reset, a reprieve."

How much of a grind is it working at The Starboard in the summer, where the staff swells to 100 from a year-round total of 45?

So much so that the apartment above Mama Celeste's Pizzeria next door, which is owned by The Starboard group, is where you can find a handful of overworked barbacks and doormen sleeping. Some have been known to even live there for extended periods.

Even so, once someone gets a job at The Starboard, they tend not to leave. The place is packed with employees who have been working there for more than a decade, drawn not only by the atmosphere, but the tremendous amounts of money to be made, especially for bartenders during the summer.

The diplomat of Dewey Beach

In 2011, Montgomery helped form the Dewey Business Partnership, which organizes and promotes family-friendly events to make the town more well-rounded — not just a place to party.

Events have included bonfire beach parties, arts festivals and the town's first restaurant week earlier this month in an effort to make Dewey more of a year-round destination. There have even been Christmas and New Year's Eve events.

"If you said 10 years ago that Bill Cosby was going to jail, Donald Trump was going to be president and Dewey Beach was going to have a restaurant week, which one would be more believable?" Montgomery cracks, noting that the town's culinary options are no longer just wings, pizza and burgers. "We're not changing who we are. We're just adding to it."

It all fits with The Starboard's growth. Since many customers from Montgomery's early days as co-owner are now older and married with children, it's not uncommon to see little ones running around the restaurant while the sun is up.

"There was a day when I knew everybody in there and now I know everybody's kids," says Montgomery, whose own children are also infatuated with the restaurant. "They have even asked me to see the security cameras at night because they want to watch and see what's going on."

In a small town where politics can play a big role — the town has a reputation for divisive elections and backbiting — some bar owners in town have struck back when they feel threatened.

Highway One Group, which owns Dewey spots such as the Bottle & Cork, Rusty Rudder, northbeach and Jimmy's Grille, once used one of its billboards to target a councilman up for re-election who had opposed a plan to expand the Cork.

Montgomery takes another tact. He generally tries to kill them with kindness, being active in the community, donating money to the police and fire departments. It's all part of a give and take.

"For a guy who hates politics, I'm told I'm very deep into it because I try to get everyone to get along. It's in everybody's interest," he says in his distinctive raspy voice, a side effect of acid reflux. Two surgeries couldn't fix the problem and just about everyone still thinks it is from him yelling in loud bars for more than three decades. 

Things did get a bit heated in 2014 when then-Dewey Beach Town Manager Marc Appelbaum told Montgomery that the town wouldn't accept a donation to help pay for more police on Memorial Day weekend, saying it could be considered a conflict of interest.

That was enough to set off the mild-mannered bar owner, who shot a letter to Appelbaum that read, "I have grown tired of the town's views of its businesses, and my will to communicate, compromise and help has evaporated due to your letter and belief that my contributions are viewed as a conflict. Count me out from upcoming initiatives.”

That heated moment thawed pretty quickly. Applebaum has since been ousted from office after making an agreement with the town in October after a flurry of allegations surfaced last summer.

MORE: Agreement reached about Dewey Beach town manager's future

For a bar owner, Montgomery has seemingly mastered the choppy waters of Dewey politics. He remembers seeing the Hearn family have to fight for their bar at council meetings and never thought he'd find himself so involved in such things.

House Speaker Pete Schwartzkopf, D-Rehoboth Beach, a friend of Montgomery's for 15 years, calls him "the diplomat for Dewey Beach."

"He really navigates those minefields that sometimes occur in Dewey," he said.

The upgrades keep comin'

One of  Montgomery's tactics at The Starboard that keeps bringing people back is constantly upgrading.

Over the years, he's added everything from video games attached to urinals to an outdoor fire pit and TVs showing short films of their special events.

In addition to replacing the bar's iconic electronic Del. 1 sign with a brighter $70,000 version last week, Montgomery also had the bar's hardwood floors replaced for $55,000 and installed new phone-charging stations. (If you stay at a bar for eight hours taking selfies and boasting on social media, odds are that you might need some juice.)

Hearn, who owns Rehoboth Beach's Ice Cream Store just off the Boardwalk, said, "Every time you go in there for the first time each season, there's something in there that makes you go, 'Oh cool, look! Oh wow, watch!' It never gets stale and other places do get stale, not mentioning any names. I mean, where else can you go for breakfast and have so much darn fun?"

The bar's daylong "Suicide Sunday" parties feature "Dewey Elvis" Frank Raines snaking his way through the crowd singing. He sometimes downs any and every shot a patron puts in his hands, usually making for an especially entertaining final couple of songs.

It is there among the Starboard diehards where you can see NBC golf announcer Steve Sands drinking a Grapefruit Crush at the bar when he's visiting town or sneaking a beer with Montgomery in his walk-in cooler. (You don't really "know" Monty unless you've slugged a quick pop in the cooler, away from the spectacle.)

Sands is one of many sports personalities who regularly visit The 'Board, including University of Notre Dame men's basketball head coach (and former University of Delaware coach) Mike Brey, as well as Gary Williams, former head coach of the University of Maryland basketball team. Since Montgomery is a big sports fan — golf, the Washington Redskins and the Washington Capitals are his loves — it makes sense.

Sands met Montgomery through a mutual friend three years ago and they have hit it off, with Sands even hosting the Montgomerys at PGA events.

"In terms of The Starboard and its success, it’s simple: Monty is everything," says Sands, who grew up in the Washington, D.C. area and has been visiting Dewey ever since he was a kid. "No one works harder at his craft, treats his staff with loving care and connects with his customers the way Monty does.

"Monty is The Starboard’s heart and soul."

Contact Ryan Cormier of The News Journal at rcormier@delawareonline.com or (302) 324-2863. Follow him on Facebook (@ryancormier), Twitter (@ryancormier) and Instagram (@ryancormier).

THE STARBOARD'S MEMORIAL DAY WEEKEND MUSIC SCHEDULE

Thursday, 10 p.m. — Kristen & The Noise
Friday, 4 p.m. — The Pips
Saturday, 2 p.m. — 19th Street Band
Sunday, 3 p.m. — Amish Outlaws
Sunday, 9:30 p.m. — Joe Bachman & the Party
Monday, 10 p.m. — Kristen & Johnny

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