Robert Dempsey is an M&A and securities deal lawyer who focuses on buying and selling middle market companies with a particular focus on health care, senior living and distressed companies. Over the last five years, Robert and his team have sold over 500 healthcare and senior living facilities. Robert’s extensive understanding of the health care and senior living industries allows him to offer tailored M&A advice to companies and private equity firms in those industries. Robert structures and closes deals across the health care and senior living industries by taking into account not only traditional corporate issues, but also the additional issues of licensure and other regulatory considerations that are integral to transactions in the highly regulated health care and senior living industries.

In addition to his middle market M&A experience, Robert also has significant experience in distressed M&A. He has represented numerous buyers and sellers in bankruptcy 363 asset sales. In 2014, Robert co-developed the Polsinelli/TrBK Distress Indices, a research index which tracks the level of distress and bankruptcies in US Companies. The Polsinelli/TrBK Distress Indices have been featured in numerous national publications including Bloomberg, The New York Times, The Wall Street Journal, The Deal, Modern Healthcare, Healthcare M&A News, Healthcare Financial Management and The Daily Journal and has become one of the leading research indices tracking distress in the economy. For more information on the Polsinelli/TrBK Distress Indices, please visit Polsinelli/TrBK Distress Indices or go to

Prior to becoming a lawyer, Robert worked in corporate finance for a Fortune 500 company. 

  • Representing Kindred Healthcare in the sale of its skilled nursing division for total value of $910 million
  • Representing Elements Behavioral Health in selling substantially all of its assets for $65 million through a bankruptcy 363 sale process
  • Representing a $1.3 billion dollar revenue skilled nursing company in the sale of seventy of its facilities 
  • Representing a private-equity-funded buyer in the $80+ million purchase of four senior living campuses in the Sears Methodist Retirement Systems Chapter 11 proceedings, involving the transfer of more than 800 beds 
  • Leading the successful refinancing and restructuring of 3 tranches of $175 million in debt for a private-equity-backed senior living company on the West Coast, including a $100 million senior secured loan, a $40 million private placement, and the contingent purchase of $35 million in junior mezzanine debt
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