Throughout school, she stayed in touch with Livingston. The summer after her second year of law school, he called to talk about a tour he had taken of western states and the mountains, and they began dating.
After law school, Cafaro landed a job as a law clerk in the 4th U.S. Circuit Court of Appeals in Durham, N.C. The couple was long distance for about two years and began talking about marriage.
"We thought about going to New York, where I had been working; we thought about going to Pittsburgh, where our families are and where he had been working," Cafaro said. "And we decided on a city that we both would feel happy about, which was Chicago."
It was a compromise, she added, "our first of many."
Career path opens up
They married in 1983 and had their first child in 1989. At the time, she was a partner at Barack Ferrazzano Kirschbaum & Nagelberg, where she worked for 13 years. Her husband, now retired, worked as an attorney for the Chicago Board of Trade.
Howard Kirschbaum, Dennis Ferrazzano and Peter Barack brought her along in 1984 when they split from Levy & Erens. Cafaro worked there with them as an associate.
Kirschbaum calls Cafaro a great businesswoman with a keen sense of which risks are worth taking. As a leader, he adds, she has a "magnetic charisma."
Cafaro developed one of the firm's major clients, Equity Group Investments, run by billionaire financier Sam Zell. He is also chairman of Tribune Co., which owns the Chicago Tribune.
During those years, she met Sheli Rosenberg, the founder of Rosenberg & Liebentritt, which served as Equity's internal law firm. Rosenberg, one of Chicago's most experienced female deal makers, became Cafaro's mentor.
"I met her when we hired her firm to do some legal work. They assigned this young, exceedingly smart lawyer to (be) part of the assignment," Rosenberg wrote in an email. "It was clear she could do the work, so I continued to ask for her when we engaged her firm. I knew I would get a good product, and because she was young, her hourly rate was considerably less than her more senior colleagues. Good work at cheaper rates — that's a bargain."
Cafaro left the firm in 1997 to lead Ambassador Apartments, a multifamily real estate investment trust.
"She said she didn't know for sure if she could do it, but it was important to try, important to grow," Kirschbaum said.
A year later, Ambassador was acquired for $682 million in stock, debt and other considerations. After selling the company, Cafaro was looking for her next project. Ventas board member Douglas Crocker, a former president and CEO of Equity, had met Cafaro through her work at Barack. After Ambassador, Crocker said, Cafaro got high marks for her honesty, understanding of the complex REIT business and her toughness. He called her.
"I said to her, 'Are you interested in taking a "mission impossible?"' That's what I called it then," he said.
She was offered the top job at Ventas in early 1999, a year after it spun off from Vencor Inc. and became the owner of most of the nursing homes and long-term care hospitals Vencor operated.
Cafaro, raising two preteens, took some time to think about the offer. The company was then based in Louisville, Ky., so she had long conversations with her parents, husband and even her baby sitter about how she would commute, about the companies being in trouble and whether the job would be good for her career.
"I took a big-picture view about the benefits of what I was doing, the sacrifices that we were all making as a family," Cafaro said. "I felt that it was worth it, and over time it would be the way that it is now, which is that I am in Chicago all the time."
When Cafaro took office, Vencor was in trouble. It defaulted on its rent several times before filing for federal bankruptcy protection that September amid rising debts and declining Medicare revenue. To keep Ventas from following Vencor, then its only tenant, Cafaro delayed paying dividends to shareholders and restructured a $1 billion debt.
Debra Cafaro, CEO of Ventas