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“Peg is the consummate professional. Extremely responsive, patient, knows the market, detail orientated but also sees the big picture. She strategized how to approach our transition and was a true partner in listing, marketing and closing the sale.” acclaim between the late 1930s and late 1970s. The artist had a part-time home and studio on Siesta Key and frequented the Crescent Club, where Condon (then Monica del Carmen Castro) was a bartender. Her time there lasted nine years, from 1970 to 1979, ending when it was time to become a first-time mother.

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A native of Chile who came to the Milwaukee area at age 4, and then eventually to Siesta Key where she lived in a variety of spots that included a little house across from Siesta Beach, Condon would next follow her husband’s career all the way to Toronto for a 30-year stay.

With each return visit to the Key throughout the years, however, she’d marvel at the fact that her portrait still shares the place with the patrons.

“I’d say to myself, ‘How can this still be here?’ I’m humbled, but also kind of embarrassed,” said Condon, now 77. “Mostly, I’m just amazed. I was just a bartender. A bartender gets a portrait?”

Nonetheless, it’s certainly an historic conversation piece for many, and even an inspiration for others.

Take Crescent Club general manager Mary Pisano for example, who started a few years ago as a server and worked her way up the ranks.

“I love seeing Monica’s picture continue to grace the walls,” Pisano said. “The nostalgia it adds to our 74-year-old bar is extraordinary.

“I love when she visits us to this day and shares her great stories. I hope one day I can share the honor of having a picture right next to hers and build a legacy and reputation as wonderful as hers.”

Visiting the bar is easy these days for Condon, considering that in 2015 she and her husband, Frank Condon, moved into the Palm Bay Club condo she had owned but had mostly rented.

She swears it’s just coincidence that she typically sits right in front of her portrait, mostly because a handful of regulars take the seats at the other side of the semi-circle bar. Of course, it lends itself nicely for striking up conversations with people who ask the bartender “Who is the gal on the wall?”

Often, people will even ask Condon, after a few looks back and forth, if it’s her.

“I get it a lot,” she said. “Especially from young people.”

Then there was the customer on a recent weekend who, within earshot of Condon, declared that he knew the person in the picture was dead.

“No, she’s not!” Condon jumped up and exclaimed. “I’m right here!”

Sadly, the only other woman whose portrait remains, right next to Condon’s on the left, has indeed passed. It’s Patty Keegan, who died while still working at the club. She spent 25 years there.

Two other bartenders (Linda Needs and the late Patty Gergen) had their portraits done by Elvgren, and both took them at the time of their departure. In Condon’s case, she was also given the green light to take the original, but tavern owner Charlie Walker asked that she replace it with as good a copy as copy possible. And she did.

“Just don’t tell anyone,” Walker, according to Condon, said to her.

“Well, I guess now the secret is out,” Condon added.

A certain mindset

“He never believed in finding bartenders, but in finding the right people,” Frank Condon said of Walker. “None of the girls back in those days had ever bartended before. And most have never bartended since.”

That includes Monica, who at 24 was recruited away from her waitress job at Red Lobster. Since then, she has been a school teacher for a second time and a marathon runner – including years of involvement with the annual Sandy Claws 5K run and walk event on the Key.

Despite being a bartending novice, Condon learned to improvise and make a name for herself.

“When my mother was in one day, she said she wanted to try these two drinks she had heard of – a pina colada and a margarita. The place was beer and shots only,” Condon said. “So, I had to bring in my own blender because Charlie wanted nothing to do with it. Well, they were a hit and added to the menu.”

Meanwhile, there was no better method to advertise that this sudden smash-hit-ofa-bartender was on duty than Condon’s yellow convertible, always parked out front. It caught many an eye, including that of her future husband, then living in a different unit of the Palm Bay Club as a bachelor.

“It was mostly locals back then, and everyone would look for that car,” Frank said. “There it is! Monica’s working! Time to stop in for a bloody Mary. ‘

“Trying to date Monica was tough. She was quite popular.”

So, it made sense that Elvgren sought her out as one of his models. Condon recalled that it took three or four sessions to get it right – he would almost be done but say

“That’s not you,” Condon said, causing him to start again.

Part of the challenge, she said, was that Elvgren was known for accentuating breasts and curves in his drawings. In the end, Walker suggested that the portraits be classy and, hopefully as a result, more timeless.

“Charlie didn’t even want any cleavage,” Condon said. “And I think he was right in that thinking. All the girls were so important to him.. We were like daughters to him.

Elvgren was the same way, despite his ooh-la-la reputation.

“He said, ‘I wouldn’t want something that didn’t feel right, if it was my daughter, on the wall forever,’” Condon said of Elvgren’s mindset.

Walker also treasured the pictures as much as anyone, so when he sold the bar after 25 years of ownership to longtime employee Julie Brown in 1990, part of the clause, Condon said, was that the interior of the club did not change. Soon thereafter, not a drawing but a beautiful photograph of Brown would join the other girls on the wall. Elvgren died early that same year, so matching a portrait of Brown with the others wasn’t to be.

The tradition continues

When Brown in turn sold the Crescent Club to Gary Kompothecras in late 2018, he too embraced the traditions and decided to leave the old-world interior intact, including the cigarette machine and phone booth, and especially the pictures.

The new, state-of-the-art outdoor sports bar would be built shortly thereafter, giving customers the feel of entering different dimensions when going through the swinging saloon doors.

“There was a rumor around town that I would level the building or make drastic changes to the inside. It was never my intention to change anything inside the bar, as it was what I loved most about the structure,” Kompothecras said. “It’s a locals’ bar and I wanted to keep it that way.

“Way too much history in that old bar. It’s my happy place.”

In fact, then-general manager Keith Green put out requests for people to bring in artifacts that showcase the history.

“I really appreciate how they kept the history in place, and so do many others,” Condon said. “And I love the outdoor area. It’s the best of both worlds.”

And, when she gazes at that stunning portrait that will likely outlast all of us, what crosses her mind?

“Well, I’m just glad something was documented from that time,” she said. “What would I say to it? I’d say, ‘You were OK back then.’” with his new windows shut, said “None of you would approve this if it were in your neighborhood.”

She’s got the picture to prove it.

Smith, who resides on Siesta Key near his establishment, has stated that he loses business when patrons leave at 10 p.m. because the live music stops.

Three other Village establishments have been granted special exceptions for live music past 10 p.m. – The Hub Baja Grill for indoor live music (granted in 1992) when the business was the Fandango Cafe, the Daquiri Deck for indoor live music (1992), and the Siesta key Oyster Bar (2001), whose permit allows both indoor and outdoor live music. However, its live shows end at midnight on Fridays and Saturdays when the business closes.

Both the Daiquiri Deck and

Siesta Key Oyster Bar are directly across the street from Gilligan’s.

The Beach Club has also had live music past 10 p.m. grandfathered into its operations. Its music is played in an indoor setting.

In a move that caught commissioners off guard, attorney Casey Colburn during the meeting’s closing public comment segment, told them that the staff report on the topic had inaccuracies. Thus, he asked them to rescind their vote, readvertise the matter, and discuss and vote again on the Gilligan’s proposal. Otherwise, the establishment would have to start all over again with a new application, which costs $7,500.

The board voted 3-2 against the request, with Smith and Detert in support.