Philanthropy: Carole Crosby Joins Forces with The Community Foundation of Sarasota County

By Sylvia Whitman
March 2021

As you might expect from the president of the Asolo Repertory Theatre board of directors, Carole Crosby cares deeply about arts and culture. It’s “what makes me tick,” she says. 

She credits her parents, particularly her late mother, Ruby, for nurturing this passion. Today, the former professional harpist—turned lawyer, turned philanthropist—celebrates that heartfelt legacy and her own personal drive to connect with others through the Ruby E. and Carole Crosby Family Foundation and the many people and organizations it supports. 

A First Career in Performing Arts

Crosby grew up in Silver Lake, Ohio. When she was five, her dad headed to Chicago on a business trip, and her mother told him to bring home a harp. It was a curious request. 

Not that Carole didn’t get plenty of presents. She was an only child, a late-in-life boon, “so unusual back in those days,” Crosby says. 

Her parents appreciated the arts. Her dad was very talented and “very, very, very literate,” into theater and Shakespeare, Crosby says. “We did all of that; we used to go to the Cleveland Playhouse.” And her mother traveled the 35 miles into Cleveland with friends to enjoy the opera during the week The Met came to town. Still, Carole had never seen a harp. She thinks her mom “just wanted something special for me, maybe something she felt she never had in her life, so she wanted something like that for me as an introduction.” 

It was love at first glissando.

Crosby attended part of third grade in Sarasota, where Ruby and her twin sister decamped for some winter sun, but otherwise she remained an Ohio girl. As a teen, she earned a spot at the Curtis Institute of Music, alma mater of Samuel Barber and Leonard Bernstein, among many notable alumni. One of great philanthropic ventures of the 20th century, the Philadelphia conservatory waived tuition for all its students, whom it selected solely for their talent and promise. For four years, Crosby practiced and performed among some of the greatest musicians of her generation.

She joined the Atlanta Symphony and after a year moved to the Detroit Symphony, becoming principal harpist. On the side, she played strings and rhythm at Motown and even played background on recordings for Marvin Gaye. After marrying Larry Wickless, Crosby settled in the suburb of Bloomfield Hills to raise their two boys. She had her career in music, and Wickless had his career in medicine as an osteopathic gastroenterologist and internist. When they could, they visited Crosby’s parents, who had landed in Sarasota’s museum district.

A Second Career in Law

After a friend applied to law school, Crosby owned that she shared the same interest, long-simmering since high school. So, she enrolled in night classes at Detroit College of Law. She had two preschool children and her symphony job, but Orchestra Hall was less than a mile from the college. “I was able to kind of cover all of that in one trip. If I had a concert, like on Thursday, I would just skip out of class a little early and drive on down and, you know, walk onstage and do my thing.”

When she graduated summa cum laude from law school, valedictorian of her class, she interviewed around town. Decision time. She couldn’t juggle a harp and a briefcase forever. She accepted an offer from a large Detroit firm. 

Even though Crosby stopped performing, she continued to support arts and cultural organizations as a patron and donor. When she and her husband needed to get away, they visited her parents and aunt and uncle in Sarasota. Or they flew to Europe, where they had an apartment in Paris, and for a while a little chalet in the Italian Alps on the other side of Mont Blanc. “I like exotic,” she says.

Their kids did well; one son became a doctor, the other a lawyer. When professor and practitioner Wickless assumed the presidency of the American Osteopathic Association (AOA), the couple moved to Chicago. There Crosby served on the board of the Chicago Alliance Française and headed the national Federation of Alliances Françaises. She also became a Life Antiquarian at the Art Institute of Chicago. 

A Third Career in Philanthropy

Chicago winters awakened the inner snowbird in Crosby and Dr. Wickless. “Trying to be open-minded,” they visited Naples, where they had friends. Then they drove to Sarasota, where Crosby’s parents and aunt and uncle are buried. Even though Crosby and Wickless hadn’t been back in a while, when they exited the highway, they drove straight to South Shore Drive, the museum district. “We went right to the old house,” she says. “I just knew that was the neighborhood we wanted to be in. And we’re still in that neighborhood although it’s our second home here.”

Once the couple settled for good in 2010, Crosby got involved in the arts and culture community, donating from her family foundation and investing her time, starting with the local Alliance Française. (She took on the national presidency for a second time, too.) She joined the Fine Arts Society, now Arts Advocates, where she eventually became board president. She patronized the orchestra, of course. Living almost next door to Asolo Repertory Theatre, she crossed paths with a number of theater-loving Detroit ex-pats. “It just kind of connected, that’s all,” says Crosby, “one connection to the next.”

Asolo Rep invited her onto the board. Theater spoke to her performing arts background. “Each performance is truly unique. It’s live one time, and even though actors may repeat the same lines, it’s never exactly the same twice,” she says. The level of artistry at Asolo Rep also impressed her. “It’s remarkable to have such a high-quality organization right here in Sarasota.”

Asolo connected her to the Hermitage, the Englewood artist retreat that awards the Greenfield Prize to a theater artist. As friends sponsored events there, Crosby attended dinners and lunches and programs. The Hermitage “is where art originates,” she says. “It allows artists to produce new works—as they say, The Art of Our Time.” She joined that board, too.

As Crosby dove deeper into local arts and culture, she appreciated how the Community Foundation champions philanthropy by connecting donors and nonprofits. Although Crosby had “pretty well determined” which organizations she wanted to support, moving the Ruby E. and Carole Crosby Family Foundation under the Community Foundation umbrella was “worthwhile,” she says. She trusts the Community Foundation to manage the endowment and alert her to new groups and projects in her areas of interest.

Partnering with the Community Foundation has freed Crosby to focus on leadership during this trying year. Arts organizations—“the heart and soul of the community”—depend on the moral support of their boards as they retrench and seek ways to connect with audiences at a distance. 

The Hermitage is holding outdoor programs on the beach, so popular now that there’s a waitlist. “They’re making a real impact,” Crosby says. “I’m delighted to be involved with that.” And the Asolo has created the Terrace Stage outdoors. “It’s like opening a brand-new theater,” Crosby says, “with lights and whatever and figuring out the seating and the ticketing. It’s been a real project.”

These days it feels good to have a purpose. Arts and culture keep her ticking.