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At a time when the healthcare real estate investment trust was on the brink of bankruptcy, leading many industry executives to contemplate their next career move, Debra Cafaro made a leap all right. She rolled up her sleeves and eagerly jumped into the REIT business. Left behind was a successful 13-year career as a finance, real estate and corporate transactions attorney.

While her departure from the Chicago-based law firm she helped found surprised some people, Cafaro believed she was ready for the move. Early in her law career, she had worked closely with Sam Zell, the Chicago-based financier who took three REITs public in the first part of the 1990s. The experience proved to be a precurser.
“The last three years of my legal career I was functioning in a somewhat hybrid role, spending half of my time on the legal side and the other half on the business side of the transactions. I enjoyed that, but I wanted to do even more,” Cafaro explained. “I believed in the business and believed that long-term care operators were performing an indispensable service in caring for the nation’s elderly. I was confident that the industry still had a future and I wanted to be part of it.”
From April 1997 to May 1998, she was president and director of Ambassador Apartments Inc. Then, she accepted the role of CEO and president for Louisville, KY-based Ventas Inc. in 1999. The company has flourished since.
Her former law partners said they still feel her absence.
“She’s one of our biggest clients, but we still miss her terribly on this end,” said Howard Kirschbaum, one of the firm’s founding partners. “She’s as effective a negotiator as anyone I’ve ever seen. She understands the big picture and has the ability to both lead and be in the trenches.”
Since Cafaro joined Ventas, her optimistic industry outlook has proved prophetic. Not only has she assembled a stellar management team and successfully reorganized Ventas’ balance sheet, she has helped build an infrastructure that has allowed the company to engage in a strategic growth and asset diversification plan.
With a $1.2 billion acquisition of Provident Senior Living Trust, which was completed June 7, Ventas’ enterprise value now totals $4.5 billion.
It is the third-largest nursing home owner in the nation, with 369 senior housing and healthcare facilities spanning 41 states. Cafaro’s success in turning Ventas around was so striking, it helped earn her the No. 10 spot on the Wall Street Journal’s “50 Women to Watch” list.
“She’s an exceptional leader,” says Ray Lewis, Ventas’ chief investment officer. “She has a way of taking a challenging situation and coming up with a win-win solution for everyone involved.”
‘One of the boys’
One may assume that being a female executive in a predominantly male-dominated industry would pose its own set of challenges, but Cafaro said she prefers a rough-and-tumble environment.
“I’ve always been one of the boys. I have a lot of energy and I’m very aggressive when it comes to what I want the company to accomplish,” she says. “I’ve never felt that I couldn’t do something because I’m [a woman].”
A self-proclaimed tomboy, she was raised in Pittsburgh by first-generation American parents. Her Italian father was a mail carrier and her Lebanese mother was a homemaker. Debra learned early on to follow her dreams and buck gender stereotypes. For example, she was one of the first co-eds at the University of Notre Dame in the mid-70s. She received her B.A. in government economics with magna cum laude honors. Then, she went on to the University of Chicago Law School where she earned her law degree with honors.
“Back then, it was the ‘in’ thing be a journalist or a lawyer,” she recalled of the period shortly after the Watergate scandal broke. “I would have been happy doing either, but law was what really drew me in. Then it was business that [caught my attention].”
So what captivates her when she’s not charting the next step for Ventas?  She likes to spend time with her family, which includes teen-agers Kevin and Katie and her husband, Terry, who works at the Chicago Board of Trade.
The foursome are sports enthusiasts who frequent Chicago Cubs and White Sox games, follow the Bulls during basketball season and root for her former hometown team, the Pittsburgh Steelers, during football season.
“I love sports. If I weren’t doing what I’m doing now or practicing law, I’d like to be a