Photo of Rafael A. Ruiz-Ayala

Rafael A. Ruiz-Ayala

Senior Counsel





Loyola University Chicago School of Law, LLM in Health Law

University of Puerto Rico, Master of Public Administration

Yale Law School, J.D.

Harvard University, B.A.

Bar Admissions


Rafael A. Ruiz-Ayala is a seasoned corporate attorney with an extensive track record as a trusted advisor to domestic and foreign for-profit, nonprofit, and public sector entities operating in a variety of industries, market segments and geographic locations. He has provided counsel to clients ranging from start-ups to public companies, including health care group practices, health and assisted living facilities, home health and telemedicine providers, and suppliers of medical equipment across the United States as well as owners and lenders of top-tier companies and public instrumentalities in Latin America. 

Rafael has considerable experience in the design and negotiation of sophisticated corporate and public finance transactions, mergers and acquisitions, joint ventures, partnerships and other strategic alliances on behalf of his clients, in the health industry with particular attention to corporate practice of medicine issues, Stark and the Anti-Kickback Statute, and the evolving federal and state regulatory frameworks shaping the industry. 

Fluent in both English and Spanish, Rafael will conduct his practice in both languages on cross-border matters as required by his clients or the particulars of a transaction. Throughout his career, he has effectively interfaced with multidisciplinary executive teams, government officials, and the public, both in the United States and abroad.

Consistent with his holistic approach to lawyering, Rafael offers his clients an ongoing relationship that allows him to provide them, during all stages of the business cycle, not only superior representation on sophisticated transactions and sensitive matters but also continuous assistance in successfully managing their relationships with relevant stakeholders, meeting their principal regulatory compliance obligations, and pro-actively assessing business and policy trends from a risk and strategic perspective while promptly responding to challenges via corrective action, process development, and organizational innovation.

Representative Matters

Rafael’s extensive professional experiences include:

  • Representing a nationally recognized physician-owned medical practice in the U.S. Southwest in:
    • the design of the ownership and operational structure and in the negotiations for the capitalization, via private placements and secured financings, of a state-of-the-art proton therapy facility, and in related secured financings by affiliates of the practice
    • the design of the ownership, operational and financing structure for a physician-led ambulatory surgical center 
    • the expansion of the practice’s geographic footprint via strategic affiliations and joint ventures with independently owned hospital facilities
  • Assisting a leading not-for-profit health insurer in Philadelphia in its acquisition of control and subsequent recapitalization of the largest membership-based not-for-profit health plan and Medicaid contractor in Puerto Rico 
  • Representing a Canadian privately held group in the design of the ownership and operational structure for a U.S. national dental plan and its compliance with applicable state insurance and marketing regulations 
  • Representing the owner of a Chicago-based home health agency in the sale of its business to private equity pursuant to a management services organization (MSO) arrangement, and a physician-led startup with the organization of a medical retail clinic and affiliated management services organization in Western Illinois, and the negotiation of the terms of engagement of staff for the clinic by the affiliated MSO
  • Assisting a medical equipment supplier based in the Midwest in the expansion of its business via the acquisition of intellectual property rights over medical devices and the negotiation of agreements with third parties for the joint development of patentable inventions of complementary medical devices, and, in connection therewith, with its compliance with applicable FDA regulations and CMS’ open payments system regulations 
  • Assisting a leading medical practice and affiliated entities in Northern Illinois in the development of appropriate physician employment agreements, internal policies and procedures for the prevention, timely detection and refund of overpayments by federal health programs and other compliance with their obligations under applicable rules of participation in the Medicare program
  • Representing the acquirer of, and subsequently acted as outside general corporate counsel to, a group of privately-owned branded restaurant and catering services chains operating in Northern California, including in the group’s dealings with lenders, landlords and employees in the ordinary course of business and the restructuring of their operations by reason of the COVID pandemic and the state and federal health regulations issued as a result thereof 
  • Assisting various U.S. sellers in the sale of interests in U.S. and Dutch entities owning and operating resort hotels in Mexico and the Dominican Republic, and a renowned Chicago-based hospitality group in the sale of substantially all its Puerto Rico assets to a New York-based operator of high-end resort properties, including the negotiation and documentation of the relevant contracts in Spanish
  • Representing a major publicly owned European publishing group in its disposition of controlling equity interests in its directory publishing businesses in the Caribbean and Central America to a leading U.S. telecommunications company, and the private owner of aircraft repair and maintenance businesses in the Midwest in their sale to private equity 
  • Acting as outside general corporate counsel to a top-tier Puerto Rico-based property, casualty and life insurance group on corporate governance, regulatory compliance and transactional matters, including the expansion of its U.S. footprint via strategic acquisitions, and the capitalization of its ventures pursuant to private placements of preferred stock
  • Representing a Chicago-based bank in negotiating a secured credit facility for the digitalization of Puerto Rico’s real property cadaster, an international bank syndicate in negotiating secured construction and permanent credit facilities for the development of a first-tier branded hospitality and retail project adjacent to the San Juan Convention Center, and the Mexican state-owned oil company in lease-leaseback financing facilities from U.S. lenders
  • Assisting either issuers or underwriters in initial public offerings of NYSE listed American Depositary Shares by leading Mexican, Argentine and Chilean companies and local offerings of limited partnership units in entities in the business of refurbishing, redeveloping, and operating major San Juan hospitality properties
  • Assisting private developers in the capitalization and financing of Puerto Rico infrastructure projects eligible to be financed, on a tax-exempt basis, with private activity bonds, including, the negotiation of the terms for the issuance and defeasance of such bonds, all limited guarantees of completion by the developers’ shareholders, any letters of credit and other credit enhancements to be issued by the Government Development Bank for Puerto Rico in connection therewith and all mortgages and security interests intended to encumber project facilities

Professional Activities

Illinois Association of Healthcare Attorneys

Chicago Bar Association

Puerto Rico Bar Association


Emerging Compliance Issues in Transactions and Alignment Panel, Health Care Compliance Association 2015 San Juan Regional Annual Conference