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Cafaro grew up in a family that loved Pittsburgh sports and she has often said that watching professional sports with her family helped to shape her as a leader. In December 2016, Cafaro became an owner and member of the Management Committee of the Pittsburgh Penguins, a National Hockey League team, who won the 2017 Stanley Cup for the second consecutive year.

Cafaro's initial actions at Ventas were to restructure the bank debt, lead a global consensual restructuring of its main tenant Vencor so it could emerge from bankruptcy (renamed Kindred Healthcare, Inc: NYSE: KND after it emerged from bankruptcy in April 2001) and negotiate a settlement with the Department of Justice on its whistle blower suit. Once Ventas stabilized in 2002, Cafaro hired an executive management team and initiated a growth and diversification strategy. In 2003 she was named the company's Chairman of the Board. The Company completed several small acquisitions and then began a series of sizable transactions including the $1.2 billion acquisition of Provident Senior Living in 2005 and the $2 billion acquisition of Sunrise Senior Living REIT in 2007 as its total number of assets grew to more than 500, with an emphasis on diversifying into private pay senior living communities. In 2010 and 2011, Ventas completed more than $11 billion of acquisitions, doubling the company’s size to nearly 1,400 properties and establishing its role as one of the largest and best performing publicly traded REITs, with total shareholder return for the ten years ended December 31, 2011, of 721.3 percent. During that same period it consistently outperformed the S&P 500 Index for each of the 1-, 3-, 5- and 10-year periods. Meanwhile, Kindred's contribution to net operating income by early 2014 was reduced to 12 percent from nearly 100 percent 15 years earlier. Growth continued and in early 2014, Ventas once again expanded its international presence with the acquisition of private hospitals in the United Kingdom. On June 2, 2014, Ventas announced $3.5 billion in acquisitions that has expanded its presence in senior living and medical office buildings. In 2015, Cafaro announced two strategically innovative transactions. First, it spun off most of its post-acute care portfolio into a pure play real estate investment trust called Care Capital Properties Inc. (NYSE:CCP), which will allow Ventas to focus on its private pay portfolio and its potential for higher growth. And, it acquired the real estate of top-ten hospital company Ardent Healthcare Services, Ventas's first push into the hospital sector. That was followed by the announcement in the spring of 2016 that Ventas would move into the life science asset class with the $1.5 billion acquisition of Wexford Science & Technology.

Under Cafaro’s leadership, Ventas was named the most successful financial publicly traded company for the first decade of the new century and in 2018 was voted as one of the world’s most admired real estate companies by Fortune magazine. Ventas is well-regarded for sustaining long-term performance; for the 19 years ending 3/31/2019, Ventas total shareholder return was 5,342%, compared with 669% percent for the MSCI US REIT Index and 180% percent for the S&P 500 Index. The Company's compound annual total shareholder return (TSR) has exceeded 23 percent since January 1, 2000.

Cafaro was hired as President and Chief Executive Officer to rescue Ventas, a healthcare REIT, in 1999 at a time when the company was on the verge of financial collapse. Its primary tenant – Vencor, Inc., which accounted for nearly all of its revenue – faced a serious cash squeeze and was unable to pay all of its rent. In addition, Ventas had $1 billion of bank loan debt and faced significant whistle blower claims related to Medicare fraud. Its portfolio of 271 senior nursing facilities and hospitals were largely dependent on Medicare payments to cover rent, at a time when the federal government’s reimbursements were declining.

Cafaro received her J.D. cum laude in 1982 from the University of Chicago Law School, where she was named its Distinguished Alumna in 2011, and her B.A. in government economics magna cum laude from the University of Notre Dame in 1979. During Law School, she was the research assistant for Edward H. Levi, the former President of the University and Attorney General of the United States, who had been appointed by President Gerald Ford to "restore trust in the Justice Department". She had summer associate stints at the law firms Jones Day in Cleveland (1980), Debevoise & Plimpton in New York (1981) and Cleary Gottlieb in New York (1982). In 1982–83 Cafaro served as a judicial clerk to the Hon. J. Dickson Phillips, United States Court of Appeals for the Fourth Circuit. Her two co-clerks, Bill Johnson and Tim Hester became the CEO of Duke Energy and the TVA, and the managing partner at Covington & Burling, respectively. She joined the firm Levy and Erens in 1983. She then helped found, as its only associate, a law firm currently named Barack, Ferrazano, Kirschbaum, & Nagelberg, LLP in 1984. From 1983 to 1997, Cafaro practiced real estate, corporate and finance law, Cafaro also taught real estate transactions and finance from 1988 to 1992 as an Adjunct Professor at Northwestern University Law School. She joined Ambassador Apartments Inc. (NYSE:AAH), a multifamily REIT as President and a Director, in 1997 where she helped to complete the successful sale of the company.

Cafaro was born in Pittsburgh, Pennsylvania to a working class Catholic family; she has one younger sister. Her mother, Dee Francis, was first generation Christian Lebanese who grew up in an Arabic speaking household in Washington PA; she graduated as valedictorian of her high school class. Her father was born in Pittsburgh to a first generation Italian family with 13 children. His immigrant father and mother owned restaurants and bars; her father worked as a letter carrier for the US Postal Service. In 1966, her father began to learn about rare coins. Pretty soon, he would take his post office paycheck and have it cashed in silver dollars. Then, the entire family would go through the coins to identify the valuable ones. By 1970, he was able to open his own rare coin store in the Grant Building in Downtown Pittsburgh. Cafaro, who was the first in her family to go to college, said that her father used his earnings from the coin store to pay for her undergraduate education at University of Notre Dame. She has said that her hard-working, close-knit family has been the inspiration for her work ethic as well as her love of sports, especially the Pittsburgh Steelers. Cafaro said that when she was 16 she became transfixed with the Watergate hearings and decided she wanted to be either a lawyer or journalist. Her father introduced her to a prominent criminal defense attorney, Tom Livingston, who introduced her to his son Terry, then a high school student who had decided to attend Notre Dame, which Cafaro was also interested in attending. Cafaro and Terrance K. Livingston married in 1983 and are the parents of two adult children.

Debra A. Cafaro, born December 15, 1957 is an American business executive, who is Chairman of the Board and Chief Executive Officer of Ventas, Inc.(NYSE:VTR), an S&P 500 healthcare real estate investment trust (REIT) with enterprise value of $37 billion that owns approximately 1200 healthcare properties located through the U.S., Canada and the UK. Cafaro joined Ventas in 1999 as CEO and President when the company’s market cap was about $200 million and was in dire financial shape. She has been widely credited with the Company’s turnaround and its subsequent success.