Frank Chester is having a week-long going away party this year: Pride. As he steps down from his position as executive director of Pride Toronto, his staff and board want to make sure that he enjoys this year’s event as much as possible.
Chester, 49, was the first staff person hired by Pride back in 1999, and has transformed that position from a part-time secretary to a full-time ED in just a few years. Pride has grown exponentially since then, and has even won an award for best festival in Canada.
“Frank has really gotten us organized,” says Pride cochair Fred Pitt. “We’re running a bit like a business now, more so than in the past.
“For Frank to be able to do that in the context of our communities, with everybody watching what Pride does and working all with volunteers is pretty amazing.” Pitt cites Chester’s work on building and strengthening Pride’s roster of sponsorship relationships as an example of his leadership.
Chester came to Pride after being on a sabbatical from his former career in computer processing. With the support of his partner, Joel Rotstein, he decided to take a year’s break after 23 years in IT.
His sabbatical saw him get involved with AIDS Committee Of Toronto, the Out And Out recreation club, the Triangle Program alternative school and Meals On Wheels for seniors. His friends looked at him and said, “Must be nice you’re not working.” He always replied, “I am working very hard. The difference is that I don’t collect a salary.”
“My one-year sabbatical, with support from my partner, ended up being a five-year sabbatical,” says Chester. “I decided to go back into the workforce not seeking out a new career, but rather I wanted to do something that wouldn’t take up all of my time and would leave me time to do the things I wanted to do in the community.”
He found Pride. And found himself in an all-consuming job that has filled many days, evenings and weekends.
“I consider myself a Pride widow,” says Rotstein, Chester’s partner of 23 years. “I’m looking forward to a break as well.”
Rotstein jokes that Pride obtained a two-for-one special because he himself got immersed in volunteering for Pride doing media and graphic design work.
“It was hire one, get one free,” says Rotstein. “It was hard because I was doing that. It came home a lot. There was no separation of church and state in that way.”
Over the past several years Pride has grown and financially stabilized. It is now recognized as one of the Top 50 Festivals In Ontario by Festivals And Events Ontario, and it won the Best Festival In Canada prize in April from Canadian Event Industry Star Awards.
Janis Purdy, Pride’s associate director, says this growth and stability comes from Chester’s skills, leadership and determination.
“He is a very smart man who thinks about opportunities. I often think of him as a chess player who is three moves ahead,” says Purdy, who will be interim executive director while the Pride board conducts its hiring process.
“Under his stewardship Pride the festival and the organization have grown tremendously – at a rate of about 20 percent per year. A lot of that is because of his capacity to think toward the future and to seek out opportunities and to jump on them.”
Purdy says that when Chester started, Pride’s operating budget was between $400,000 and $500,000. Last year it was $900,000.
“He’s very socially liberal, fiscally conservative. He has taken great care with the organization’s budgeting and financing. Since he has been here Pride has not run an annual deficit,” she says.
Chester is quick to point out that Pride’s success comes primarily from the volunteers.
“The contribution that I have made and been able to make is to take the ideas and the vision of the board members and the volunteers that organize the event and to see those things to fruition,” he says.
Chester, who has been known to leave scolding telephone messages for people with whom he disagrees, deflected questions about conflicts he’s had over the years. For example, the public blowup in his first year as ED with Enza Supermodel when she expressed an interest in being on the Pride board. Chester met with her to discourage her from doing so. Still, Enza says she’s sad to see him leave.
“It’s been resolved. I didn’t get on the board but I have no bitter feelings toward Pride,” she says. “We had our disagreement but we still said hi to each other when we saw each other at events.”
Purdy hopes that this year’s Pride Week celebration will allow community members to let Chester know how much he is appreciated. During the parade, he’ll be seated at the judge’s table to ensure a bird’s-eye view.
“He always jokes that he never gets to see the parade and we’re making sure that he does this year. Everyone who waves at the judges can wave at Frank as well,” says Purdy.