How Aspen’s Boogie Weinglass went from broke to a billion

“Their Generation,” an ongoing series profiling longtime locals of the Roaring Fork Valley, runs every other week in The Aspen Times.

Born in a black neighborhood in Baltimore, Leonard “Boogie” Weinglass got his nickname for his dance moves.

He was rough, dirt-poor and good with girls. He bounced around from school to school. In one instance, he was expelled for stealing a few hundred blank report cards and selling them to his classmates.

He was an all-state basketball player at an all-black high school. As a fight-picking, girl-getting teenager, Boogie would show up on the big screen in 1982, with Mickey Rourke portraying him in “Diner,” a breakout role for the actor.

At 21, Boogie was married. At 22, he was divorced. He didn’t have enough money to make it through college, so he found a job working in a basement at a women’s clothing firm in Baltimore. But all the girls were on the first floor in the accounting department, so he didn’t always stay in the basement.

“The boss said, ‘Boogie, you come up here one more time, I’m going to fire you,’” Boogie, 72, recalled last week over an omelet at his diner on East Cooper Avenue.

The day he was fired, Boogie, with long hair and filthy clothes, found his way up to the second floor, above accounting, and knocked on the president’s door. Boogie introduced himself as Lenny Weinglass, and the president said, “You mean Boogie?” The man’s nephew had played basketball with Boogie.

“Sir,” Boogie said, “I think I would like to sell the clothes that I’m packing.”

“Well, have you ever sold before?” the man asked.

“No sir, but I can sell anything,” Boogie responded.

The man phoned the sales manager in New York, and an interview was scheduled for the next day. After training and a month on the job in Atlanta, Boogie was one of the company’s leading salesmen. But two years in, Boogie “got screwed” out of around $6,000 in commission, by today’s standards. Despite the hard-headedness he developed as a child, Boogie didn’t quit. He kept working until he developed the concept for Merry-Go-Round — a clothing store he would open and turn into a billion-dollar chain.

The idea to open the first store came from a visit to The Different Drummer, a hippie boutique store in New York with a sign out front asking, “Tired of the same old shit?” Boogie walked in and was met by two saleswomen, wearing short pants, high heels and tight T-shirts. They took his sport coat off and dressed him in a pair of jeans and a T-shirt.

“And I liked the way I looked in these jeans and this T-shirt,” Boogie said. “I realized I had a good body, and I looked good, and she said, ‘That’s a lot better.’”

He brought the idea back to Atlanta in 1968, when few locals had ever seen bell-bottom blue jeans or see-through mesh shirts. He also sold head-shop items at the store, which was two blocks from Georgia Tech and other schools. Merry-Go-Round was successful immediately, selling out of almost everything in the first two weeks.

Taking a sledgehammer to the wall, Boogie expanded into the next-door space in less than two months. The store was unique, and it was profitable. Boogie bought vintage U.S. Navy peacoats, cleaned them up for about $3 apiece and sold them for $35 each. Kids also liked his floppy hats, trendy boots and store-made sandals.

Demand for Merry-Go-Round continued to rise, so he opened a store directly across the street called Sexy Sadie.

“I basically carried the same shit,” he said of the two competing stores. “I didn’t have to even look at new stuff. All I did was change colors.”

By 1970, he was running four stores, and a friend from Baltimore, Harold Goldsmith, showed up. This led to a partnership that landed Merry-Go-Round a retail space at Atlanta’s famed Lenox Square shopping mall.

While Boogie, the merchant, dealt with the longhairs and continued opening stores, the younger, more clean-cut Goldsmith complemented him by signing leases and dealing with banks and computer systems.

Boogie previously had tried for a space at Lenox on his own. But the mall manager was unimpressed with Boogie, who, by his account, looked like a “second-class drug dealer” pedaling bell-bottoms and hippie culture.

Goldsmith lined up a second interview with the manager, and this time, he had Boogie cleaned up and wearing a suit. With his charisma and knowledge, Boogie came to an agreement with the man, who owned another 80 upscale mall locations.

By the early 1990s, they had 1,500 stores, a 1 million-square-foot warehouse in Baltimore, and they had reached $1 billion in sales, which by Boogie’s estimate is around $3 billion today.

Boogie jokes that it was a woman who brought the billion-dollar firm down, but it was a series of events. Gabrielle Pepper, whom he had been with on and off in Baltimore for three years, was in Aspen. Boogie chased after her in the early 1980s and asked her to marry him.

She said, “If I say yes, can we live in Aspen?”

In 1987, he opened Boogie’s Diner, a view-blocking structure his detractors called the “Boogification” of Aspen. Because it was independent from the Merry-Go-Round corporation, the building is the lone survivor of the chain’s collapse in 1996.

One of the reasons for the decline was the 1991 death of Goldsmith, whose private plane crashed on Boogie’s property in Aspen, which runs parallel to the airport. He and two others who were killed had departed from Las Vegas.

Running the business solo from Aspen, Boogie was no longer looking at any of the clothes. By the time he traveled to Baltimore, it was too late. The warehouse was filled with about $30 million worth of outdated bell-bottom jeans and peasant tops, clothing that had been irrelevant for decades.

There was also Merry-Go-Round’s acquisition of 500 Chess King stores, a major bust due to the retailer’s bad locations and old stores. Boogie said that it could have been overcome had the Merry-Go-Rounds been doing business. But they were competing with a new trend: preppy stores like Abercrombie & Fitch, J. Crew and Eddie Bauer.

Boogie owed the bank about $200 million, and money wasn’t coming in. By then, he had seven or eight Boogie’s Diners attached to stores in Los Angeles; Las Vegas; Chicago; Washington, D.C.; and New York, among other cities. The diners, along with 536 stores, were shuttered in February 1996.

Well-known for his generosity toward diner employees, Boogie has been a steadfast supporter of Aspen’s Buddy Program, as well. According to the organization, which honors him with Boogie’s Buddy Race on the Fourth of July, Boogie has raised and donated millions to his various charities and foundations, with a focus on the Buddy Program.

It wasn’t until May 2012, when he decided to make time for travel, that Boogie stepped away from his Aspen diner and its Lil Boogie’s counterpart. Because his three kids — Sage, Skye and Bo — weren’t ready to take over, he handed the reins to three local restaurateurs who had impressed him with their work at Over Easy.

Six months later, Boogie was diagnosed with cancer and took a harder look at the future. With Over Easy management failing to wow, Boogie turned to his kids, who have been managing the businesses since.

“If my diner, if this business doesn’t run smoothly without me, I’ll be forced to sell this building,” Boogie said. “I want people to come in and see good clothes and eat good food and have fun.”

What he would like to see is an expansion similar to Merry-Go-Round.

“If I were your age and I was younger,” Boogie told his son Bo, “I would take this public. But you’ve got to learn this business. You’ll learn it.”

herk@aspentimes.com