If the citizens of Sarasota have a defining characteristic, it’s reinvention. After a successful career in business or the arts or education, they decide it’s time for another challenge. All that expertise they acquired over the years is still there, itching to be used, and the timidity and insecurity of youth have long been forgotten. Now it’s time to flex their muscles and do something really worth doing. It’s time for a great second act.

The astonishing turnaround at the Westcoast Black Theatre Troupe is the latest example. After bouncing around for 10 rocky years, with critical and popular respect but shaky financial support and management, WBTT has suddenly become the model of how to run an arts organization in Sarasota. And the turnaround has given three longtime Sarasotans the role of a lifetime. For Howard Millman, the former producing artistic director who led the Asolo Rep back to success after it faltered in the mid-1990s, it’s turned quiet retirement into a chance to work his legendary magic once again, establishing him as the Grand Old Man of Sarasota theater. For former banker-turned-politician Christine Jennings, rescuing the troupe has helped redeem two failed congressional campaigns. And for WBTT’s founder, Nate Jacobs, it’s been the rush of seeing his ragtag theater troupe, after a decade of performing on risers in arts centers and church basements, become the hottest act in town.

The Westcoast Black Theatre Troupe began backstage at the Asolo one night in 1999, in the mind of Nate Jacobs. He was performing in a play at Asolo Rep. Over the previous several years he had done several plays there. As an actor he had a wide range, and when you needed an African-American in a part, Nate was usually the first person you thought of.

While Nate considered himself fortunate for his success, other aspects of the situation bothered him. There was a lack of diversity in the Sarasota arts scene. The African-American population of the county was only 4 percent, and opportunities for a black actor were limited. As he waited to go onstage that night, the only dark face in an all-white cast, playing to an audience that was almost 100 percent white, he made his decision. “I won’t be back at the Asolo,” he told himself. “I’m going to develop a platform for people who look like me.”

Nate was an unlikely candidate for social and artistic change. A shy, introverted kid, he grew up in Tampa and Daytona Beach. His parents were musical—his father ran a touring gospel group—but the theater wasn’t a part of his upbringing. He remembers the first play he attended, Hansel and Gretel, when he was in third grade. “I thought it was the most wonderful thing I’d ever seen,” he says, his eyes still lighting up at the memory.

But his shyness kept him away from performing until he entered Florida A&M University in Tallahassee. He’d always made up stories to entertain his siblings—nine brothers and a sister—and now the talent came in handy for making friends. The stories were mostly about a naïve 16-year-old girl named Emmeline and how she looked at life. Nate would act out all the parts and, encouraged by the laughter, the stories soon became little plays. A teacher saw them, and when an actor in a college play dropped out, talked Nate into playing the part. “You’re a natural,” the teacher told him.

After college he moved to Sarasota to teach art at the Westcoast Center for Human Development, a church and school run by a prominent minister in the African-American community, Dr. Henry Porter, and his wife, Cynthia. There Nate discovered another gift—for teaching and mentoring. Acting in local productions soon followed, capped by the establishment of the Westcoast Black Theatre Troupe in 1999. Dr. Porter’s ministry was largely a musical one, and the congregation provided a steady stream of talent for WBTT shows.

Over the years Nate had developed a style all his own. At its core is his encyclopedic knowledge of African-American musical styles over the past 80 years—his first show was a Cotton Club revue. A small cadre of Sarasota theater lovers began seeking out the talented young performer and his new troupe. It wasn’t always easy for the troupe’s fans, as the company was nomadic, changing venues from season to season, sometimes in obscure locations. And it took a while to get the mix of shows right, too. Audiences tended to respond more to the musicals (including Dreamgirls and Five Guys Named Moe) than the dramatic plays WBTT occasionally did. Musical revues, providing lots of memories for Sarasota’s typically older audiences, tapped into the natural talents of the performers and were also crowd pleasers—the more the atmosphere resembled gospel or Motown, with the audience clapping and swaying along, the more successful the evening.

But if audiences took to them, they still had trouble finding and following them. For a while the troupe performed at the Historic Asolo Theater, but the venue was expensive and not really suited to their high-energy style. A move to Art Center Sarasota showed that a more intimate setting, with the audience right in the middle of the performance, was a better solution. But the center’s own needs for the space required that the set be taken down each night, then reassembled the next day for the next performance.

There were other problems as well. An artistic dynamo who produced, sometimes wrote and directed and acted in all the shows, Nate also had to tend to the business side of running an arts organization—a full-time job in itself, and not his strong suit, as he is the first to admit. But with Nate and the board and a group of volunteers having to do everything, from selling tickets and creating publicity to paying bills, crucial details started to fall through the cracks. The troupe began to get a reputation for being disorganized as well as poorly funded. The board, though supportive, was not raising enough money to sustain the company, and little was being done to address long-term planning or growth. Howard Millman, who joined the board in 2007 at the urging of volunteer Eva Slane, sat through the meetings, watching the turmoil as things got worse and Nate became more discouraged. Finally, in 2008, he asked Nate to join him for coffee at Starbucks.

Howard had recently retired from running—some say “saving”—the Asolo theater. When he took over in 1995, the venerable Sarasota institution was on the verge of bankruptcy and had lost its sense of direction. Howard put together a coalition of Sarasota movers and shakers, turned it around financially, and re-established it as one of the country’s leading regional theaters.

He hadn’t said much so far during the WBTT board meetings. He spent his time listening and evaluating, putting the pieces together.

Nate was in a gloomy mood that day. “It looks like we’ll have to shut down,” he said. “Shut down and start up again later.”

“I guarantee that if you shut down you’ll never reopen,” Howard replied. “That’s what always happens.”

“Then what should we do?”

The coffee at Starbucks changed the two men’s lives. Howard was a few years into a well-deserved retirement, guest directing at various theaters around the country and being half of one of Sarasota’s power couples—his wife, actress Carolyn Michel, has long been active in the local arts and philanthropic scene. Now, with a distinguished career behind him, he could rest on his laurels, play golf, help Carolyn learn her lines, accompany her to the many benefits she was involved in, and travel the globe. But he’d always reveled in the excitement and fulfillment of the theater; he wasn’t exactly bored, but after his adrenaline-fueled career, life sometimes seemed a little bland.

He also had the perfect background to save the Westcoast Black Theatre Troupe. He’d done it before, at the Asolo. Could he do it again? Did he even want to? What made the troupe worth saving?

The answer to that question was simple. “Talent,” Howard says emphatically. It was a career-launching kind of place. One of the performers, Teresa Stanley, had gone on to appear on Broadway in The Color Purple, and more recently 14-year-old Chris Eisenberg had done a great job on the TV show America’s Got Talent, making it to the semifinals. (A few weeks ago, Eisenberg was back with WBTT in a new show based on the life and music of the legendary Cab Calloway, playing the young Cab.)

But for Howard, it was mostly faith in the talent of Nate Jacobs. Nate had a showman’s instincts, and onstage he was fearless. Audiences had long been delighted with his one-man show featuring his “Aunt Rudele” character, a potent black matriarch along the lines of Tyler Perry’s Madea, and he had performed her to great acclaim, both locally and at theater festivals. Just last season, when an actress dropped out of Jar the Floor, a comedy-drama by Cheryl L. West, days before opening, Nate stepped in and played the part. It was much more than a comedy performance in drag, critics reported.

A plan was forming in Howard’s mind. The first step was a meeting with Debra Jacobs, at that time the head of the Selby Foundation. “What Nate needs is a full-time executive director,” Howard told her. “He needs to be freed up from running the organization so he can concentrate on the artistic aspects.”

Debra Jacobs made a suggestion. Before approaching funding sources, she said, they should have a definite person in mind for the job. Several names were brought up. Sarasota is home to many competent arts administrators, and the talent pool was definitely there. Then Debra had an idea. “What about Christine Jennings?”

Howard laughed. “You think she’d be interested?”

Christine Jennings is one of the most recognizable names in Sarasota. Legendarily hardworking and upright, she had raised herself through the ranks of the male-dominated banking industry. When she saw that few women ended up running banks, she founded her own—Sarasota Bank, which grew and prospered and was sold to Colonial BancGroup in 2003 for more than $40 million. Conservative, stiffly coiffed, and often dressed in expensive St. John suits, she had succeeded in a very Republican industry in a very Republican town, but she came from a blue-collar background and was a lifelong Democrat. After selling the bank, she decided to put her political beliefs into action and run for Congress against current representative Vern Buchanan. She put herself through exhaustive training in fund raising and organization. The first campaign, in 2006, was a bruising experience. In the final vote count Buchanan was 373 votes ahead, a tight margin clouded by an 18,000-vote “undercount”—ballots cast with no candidate selected for the Congressional seat. After lengthy and exhausting recounts and court cases, Buchanan’s victory stood.

A second campaign in 2008 was less of a toss-up, with Buchanan well in the lead. The entire process was five years of grueling work and broken dreams. And now that it was over, it left Jennings in a difficult position. What to do next? Retirement held no appeal. (Jennings is in her mid-60s.) An ordinary job would seem pointless at this stage in her life and after all her accomplishments. Her foray into politics had boosted her self-confidence but left her frustrated.

Jennings listened carefully to Howard’s proposal. When she heard the troupe’s only answer to its financial problems might be bankruptcy, she bristled.

“I hate that word,” she said vehemently.

She asked for some time to think about it. The more she did, she realized the possibilities. True, she had no experience with a theater. But she had served on many nonprofit boards —including the Ringling Museum, Sarasota Film Festival and Sarasota Ballet—and she had run a bank. She had also long sympathized with minority challenges and causes. And two political campaigns had turned her into an extraordinary fund raiser. She knew when to charm, and when to twist the arm. And she, like Nate on stage, was fearless.

Christine finally agreed to the job, with one proviso: that her friend and advisor, Michael Shelton, also come on board for six months as a consultant. Michael had worked with Christine before on various projects, including her campaigns. (He is now managing director of the Sarasota Ballet.)

Together they began to sort out the theater troupe’s confusing situation. “We worked night and day,” Christine recalls. “It was as much work as starting a new bank.”

Records had not been correctly kept, and the financial picture was hard to piece together (“We were going through drawers,” Christine remembers), but with the help of Cheryl Anderson, an accountant with Cavanaugh & Company who was brought on the board, they finally arrived at a reckoning. One crucial fact was clear: “There was nothing here that couldn’t be fixed.”

Christine and Michael’s first project was to put together a 30-page business plan. New board members were recruited, including local heavy hitters like realtors Michael Saunders and Roger Pettingell and philanthropist Mary Ann Robinson—who asked to join, so firmly did she believe in the group.

African-Americans also came on board, including Mike Rosario and Samuel Hicks. The board currently has 17 members—soon to be expanded to 21—and their financial support of $2,500 each in yearly dues made all the difference in keeping the group alive.

Next Christine set out to eliminate the organization’s debt, which totaled $150,000. She began negotiating with each creditor, working out a settlement or a payment plan, even if it was just $25 a month. In consultation with Nate and Howard, investments were made in lights and equipment, office space was found, and retired marketing executive Michael Gardiner funded a marketing plan that resulted in the sale of more than 1,000 new subscriptions. Ticket prices were intentionally kept low—currently $75 for a four-play season—and the results paid off. This season practically every show was sold out.

There was nothing halfway about the group’s approach. It was essential to make the theater troupe a cause célèbre in Sarasota’s small and close-knit social circle, and a 2009 season kickoff fund raiser was planned at Michael’s On East. All of the networking skills that Jennings perfected during her political campaigning were put to use, and the ballroom was packed with a Who’s Who of socialites, business leaders and arts lovers, 350 of them. She, Millman and Jacobs worked the room relentlessly, urging everyone to buy season tickets. The climax of the night was a sensational show by the troupe, a musical preview of the season to come. By the end of the evening, most of the audience—including Jennings herself—were on their feet, moving and clapping to Motown rhythms. The evening was so successful that the following year, when the party was reprised, the event was held on two successive nights to accommodate the demand—a Sarasota first.

One problem remained, though, and it had to be addressed. “We were gypsies,” Howard recalls. “Nobody knew where to find us.” A permanent home had to be found if the troupe was to enjoy continued stability. They started looking, but finding the right place was difficult.

At a performance one night, Christine bumped into an old customer from her banking days. They went out for a drink after the show, and she told him about their search. The next morning he called her and said, “I think I have the place.”

There’s a not-so-hidden subtext in the drama of the Westcoast Black Theatre Troupe, and it has to do with race. The recent murder of two British tourists in the Newtown area prompted the community to stop a moment and see where it stands. And what most people saw wasn’t good.

To begin with, Sarasota is an affluent, sophisticated town where appearances count and the right lifestyle is important. Many Sarasotans, particularly those who live on the keys, can go for months without entering or even being reminded of “the poor side of town.” Like most Southern towns, Sarasota still has a city geography based on the days of segregation—the African-American part of town is to the north and has been for generations. And it’s the complicated mix that most such places are—unemployment, inferior housing and crime and drugs side by side with strong family values, fierce civic pride and powerful churches. The cultural and lifestyle differences between the two communities seem vast.

Unless you’re at the new home of the Westcoast Black Theatre Troupe. It’s located at the intersection of Orange Avenue and 10th Street, where downtown meets Newtown. And that could describe what’s going on inside, too. At a recent performance, there was a racial mix unusual in Sarasota. Christine Jennings welcomed the crowd. She is, of course, not just white, but extraordinarily white—pale, milky skin and platinum hair. The casts of the shows are mostly—often exclusively—black. The band is half and half (sometimes with a white musical director, James Dodge II), as is the technical and house staff.

And the audience? Every theater audience in Sarasota is mostly white and mostly gray-haired. This one is no exception. But there are quite a few black faces, and the percentage is growing with each show. “Our goal is to have the audience one-third African-American,” Howard says.

There is no doubt that the Westcoast Black Theatre Troupe is on a roll. At a time when most arts groups in town are experiencing financial setbacks and hardships, it’s flourishing. It’s turned Nate Jacobs from a marginal player to someone to be reckoned with—a major talent in performing, directing and developing new plays.

“It’s a wonderful time for us,” he says. “We finally have the right combination.”

Howard Millman has the satisfaction of seeing a lifetime of hard work benefit the community in a way he never expected.

“It stirred my juices up again,” he says with a smile. “I just turned 80, and I’m still cooking.”

And it ensured that Christine Jennings landed on her feet. She had to make this work, and she did, brilliantly. They make an unlikely partnership, this trio, but working together, they reinvented themselves, and in doing so, are reinventing Sarasota.