“The talent is coming from everywhere,” said Cutler, 84, who is planning to pick up the bulk of an estimated $2 million tab unless other sponsors step forward to help.

The millionaire philanthropist is resurrecting Outside the Box, his free, multiday event, which will return to Boston this summer following a yearlong hiatus prompted by management woes and spiraling costs.

Cutler said that since launching the festival, which drew thousands to Boston Common and City Hall Plaza in 2013, he has been honing his vision for the event, building partnerships, and scouring Boston and beyond for top entertainment talent.


“How do you judge performing arts? I’ll tell you how I do it: Good is good, and bad stinks. That’s all,” said Cutler, who works closely with his staff but has ultimate say over which acts are invited to perform.

This year’s festival, though slimmed down from 2013, will still be immense: a six-day extravaganza featuring more than 70 acts on three outdoor stages, July 14-19. Headliners have not yet been named.

Cutler has created a partnership with Greater Media Boston (which owns radio stations Country 102.5 WKLB, 105.7 WROR, Magic 106.7, and WBOS Radio 92.9) to feature national musical acts. They plan nights devoted to country music and classic rock, and will incorporate Radio 92.9’s EarthFest, an annual concert staged at the Hatch Shell in the past. In addition, the event will feature two nights of music performances programmed by the Emerson College radio station WERS.

“Teddy explained his vision for Outside the Box going forward, and I loved it,” said Rob Williams, vice president and market manager for Greater Media Boston. “He said he wanted this to be here a generation from now.”

Cutler said his festival will also feature everything from local theater and dance troupes to international acts, and a sprawling section for children that will feature arts education.


Arts patron and philanthropist Ted Cutler. Pat Greenhouse/Globe Staff/Globe Staff

“Our festival plays to everybody in the city of Boston,” Cutler said. “It’s family entertainment.”

For Cutler, a Dorchester native who made his fortune organizing technology trade shows, the festival is a singular passion: an opportunity to give back to the city he loves.

“We found out that a lot of people from the city of Boston, that was their first concert,” Cutler remarked of the 2013 festival, which he said hosted more than 650,000 visitors. “It’s just showing . . . how important it is to take these kids who should be studying the performing arts and giving these kids a chance to see it.”

He estimates that producing this year’s festival will cost roughly $2 million.

“I have no partners on this. We are out there raising money. It’s going to take time,” he said. “But we do have people waiting in the wings.”

During a wide-ranging conversation in the wood-paneled den of his tony Back Bay home, Cutler said it was his late wife, Joan, who first inspired him to become a philanthropist and arts benefactor.

“She said, ‘Why don’t we help other people who have not been so lucky,’ and from that day on I’ve not taken a paycheck,” said Cutler, pointing to a portrait of him and his late wife prominently displayed on one of the room’s walls.

He added that after the first festival, people have been stopping him on the street to ask if the event would return. “‘When are you coming back? Are you really coming back?’” he said, recounting the conversations. “These people can’t wait, and I can’t wait to give it to them.”


When it debuted in 2013, Outside the Box featured more than 200 acts performing over nine days on seven stages on the Common and City Hall Plaza, including such crowd-pleasers as the Mighty Mighty Bosstones and Los Lobos.

But the festival had difficulty attracting outside sponsors and ended up personally costing Cutler nearly $6 million. Internal strife among staff added to the turmoil, which became public after the festival’s artistic director and associate curator resigned in advance of the event.

“They couldn’t get along with the guy who was running it,” said Cutler, who now works with a core staff of six. “The first thing we did was change our staff, because the staff has to get along together, and that staff did not get along together.”

Cutler has rehired Georgia Lyman, who resigned as associate curator in 2013, as the festival’s artistic director.

“The focus this year is definitely honed and a little more streamlined,” said Lyman, who added that the work environment this time around is “wonderful.”

Cutler says he has also worked to bring costs down, working with Greater Media Boston to provide talent and shrinking the size of the festival, which will now take place only on the Common.

“We can’t just put $6 million to work every year,” he said. “I want to make it sustainable so one day the city might take it over, or the state might take it over.”


This year, he has personally pressed ahead with programming, working with several foreign consulates to provide international music and dance troupes. Closer to home, he’s signed everything from the hip-hop dance group the Floorlords to a children’s juggling act, the Aerial Comedians.

“The children’s section is particularly vibrant and very interactive,” managing director Susan Shields Darian said. “One thing we’ve all gotten from Ted is that without access and exposure [to the arts] there can be no inspiration.”

Matti Kovler, composer-in-residence at the Elie Wiesel Center at Boston University, will be presenting the English-language premiere of his musical “Ami & Tami,” and Jacqui Parker is creating a one-hour performance that combines spoken word and movement to explore the African-American experience.

“I’ve made a study of these people. They’re not good — they’re great,” Cutler said. “But they’re playing in the cellar of a church or a synagogue or some little broken-down place. We want to give these local people the opportunity to get up onstage, and don’t play to 40 or 50 people: Play to 4,000 people.”

To demonstrate the point, Cutler said he had just seen a duo at a restaurant on the Cape. One man played the guitar. The other played an “electrified thing.”

“They were terrific. They’re in the restaurant; everybody was applauding for them. I took their card,” he said. “I want to put them in as a filler.”


Malcolm Gay can be reached at malcolm.gay@globe.com. Follow him on Twitter at @malcolmgay.