Dan McCaffery was about to start his ninth year as a high school principal in Canada when his bosses hinted that a promotion would send him downtown to the central office. He didn’t want to leave the students he’d taught and coached.

“I still love teaching, but more of my time was administrivia,” he recalls. His wife Iris, his confidante since junior high, suggested he try something elsereal estate, perhaps. She sold properties and knew he had the charisma and persistence to outperform.

“She schemed with her girlfriend, whose husband was a construction engineer, to have me introduced to a company that built high-rise buildings,” McCaffery says. “So, I left teaching of my own volition, with a little needling.”

He joined Oxford Properties Group, the largest development company in North America, and began a second career that seemed to be a natural evolution. “Business is teamwork, and I got a good smack of what it takes to be a leader in the classroom,” says McCaffery, 69, the man whose vision will soon transform Pittsburgh’s iconic Produce Terminal, once the hub of the Strip District. (See accompanying article about the Produce Terminal here.)

Produce Terminal Building

The Produce Terminal on Smallman St. in the Strip District. Photo by Elan Mizrahi.

Tenacious, forthright and gruff, McCaffery also is a good listener. He built a reputation as a careful developer and put thought into his motto, “Thoughtful and creative real estate solutions,” for Chicago-based McCaffery Interests, which also developed Cork Factory Lofts and Lot 24.

“We felt him to be not only an innovative and flexible and reasonable developer, but also someone who’s very patient,” says Kevin Acklin, Mayor Bill Peduto’s chief of staff and head of the Urban Redevelopment Authority. “He knew this (terminal) is a crown jewel for the city and one in which there is a lot of interest.”

Oxford moved McCaffery to Chicago from his home in Edmonton, Alberta in the late 1980s, to develop Quaker Tower, an office building, and Chicago Place, a vertical mall. His salesmanship soon made him an executive, but by the time he was 40, Oxford was selling its U.S. business and McCaffery felt vulnerable as a senior vice president.

The company chairman, a friend and mentor, helped him start the commercial real estate company that today has more than $2 billion in assets and developments. Since starting McCaffery Interests in 1991, he has built apartments, shopping centers, hotels and master-planned communities.

“Sometimes you’re in the comfortable pew, right? I think extracting yourself from that comfortable pew makes it hard, but to be honest, it didn’t stay hard for me very long,” he says of striking out on his own. “I don’t think I had more than two or three months where I worried if I was going to make it.

“There’s something beautiful about the opportunities in the U.S. and Canada to have your own company. You work a little harder, but it’s you. I love that. You don’t do it for money. It’s got to do with self-fulfillment and leading your own life.”

Produce Terminal rear

The back of the Produce Terminal Building which faces the Allegheny River. Photo by Elan Mizrahi.

‘A funky project’

As CEO, McCaffery still personally checks out any property his company might develop. Associates have described him as a take-charge businessman who can get something done with one phone call. “I am blunt,” he says. “No point in being a schmoozer all the time.”

Some thought he was crazy to take on the landmark Produce Terminal, a largely abandoned, five-block-long auction and delivery building. More than 100 years old, it edges Smallman Street from the 16th Street Bridge to 21st Street, where the historic St. Stanislaus Kostka Church sits.

“It’s a one-story buildinghow funky is that?” McCaffery says. “That building will mean a lot to the city and the Strip District if we do it rightand there’s no doubt in my mind that we will. That building has a uniqueness to it, and now we’ve got to make it successful.”

Across the street, the warehouse at 1600 Smallman that he’ll also renovate looms large and dark. “The bones of that building are so beautiful, but it is ugly as sin,” he says.

The URA chose McCaffery as developer for the terminal three years ago, and the project continues to generate debate. Numerous meetingsincluding one on January 18 at Contemporary Craftdon’t deter McCaffery. He’s had projects that required 45 public hearings.

A big, empty building “can sit there for a hundred years without someone having an idea, but as soon as you have an idea, they have more,” he says. “There are days when I want to scream. You have to live with that in development.”

He anticipates starting late this year to build retail, office and restaurant space in the terminal.

The final piece is financing, says Acklin, who estimates the project cost at more than $50 million, including infrastructure improvements to Smallman. Acklin holds weekly meetings to discuss progress. The street and utility work is awaiting approval of tax increment financing, but the city has at least $4 million in state grant money.

“The building is one piece of this redesign of the street, which we think is a transformational opportunity having that not only safe for cars, pedestrians and businesses, but a public plaza at St. Stanislaus that harkens to European squares,” says Acklin. “The public realm investment, these dollars that we’re raising, aren’t going into Dan McCaffery’s pockets.”

McCaffery family

The McCaffery family at the the 25th anniversary of McCaffery Interests in January in Chicago. This photo and above © 2016 Jason Muelver for Collin Pierson Photography.

Close family

McCaffery says it’s too long ago to think about but he suspects he and his brothers learned the value of hard work from their early upbringing.

When he was 10, the family moved from the small city of Newry in Northern Ireland to Eldorado, a uranium mining town in Saskatchewan. His father was a camp steward but he left the family a year-and-a-half later, and his mother took them to Edmonton.

Without a father, “teachers and coaches loomed big in my life.” McCaffery became a standout athlete at the University of Alberta, where he ranks in the Hall of Fame as a quarterback, defensive back and co-captain of the Golden Bears. He ran fast but weighed too little to make it as a pro when he tried in 1971, and he became a teacher and coach when the Edmonton Eskimos cut him after four games.

He still plays tennis, but says, “I’m really getting good at taking it easy. I love golf because it’s a good walk in the park, with friends and your wife. I don’t trouble myself with being good at golf.”

He and Irisgrandparents in a family that’s grown to 16own a second home in Florida. McCaffery’s oldest son and a son-in-law work for him and McCaffery has instilled in all his employees the value of spending time with family.

“We try to do small things to tell families they count,” he says. “It’s nice. They never have to worry about taking time off for a school play, or whatever. If it’s got something to do with family, we turn a blind eye. We’re very fortunate.”