James C. McCaskill


(P) 919-645-4318
(F) 919-540-6802

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Jamie McCaskill focuses his practice on commercial real estate. He represents clients with real estate interests in a broad variety of matters, including the acquisition, disposition, financing, development, leasing and management of real property across all asset classes located throughout the United States. When working on real estate transactions, Jamie further assists his clients with the formation and negotiation of partnerships, limited liability companies, and other business organizations.

Jamie also provides services to the capital markets industry and serves numerous banks and other financial institutions in various types of construction lending and other commercial financing transactions. He has represented national banking organizations and large credit unions in multiple real estate backed commercial loan originations collateralized by assets located throughout the country, including several loans made in connection with single-tenant assets leased by the United States General Service Administration.

In addition, Jamie provides counsel to lenders on real estate workouts financial restructurings and other distressed debt transactions. In this regard, he reviews and analyzes lender remedies under loan documents and other legal papers before advising them as to the rights and obligations of all parties and assists in the repositioning of any distressed assets in receivership or acquired through foreclosure.


Practice Areas:
Contracts & Commercial Agreements
Real Estate Finance & Capital Markets
Distressed Debt & Workouts
Real Estate Investment & Development

North Carolina



Accredited as a Leadership in Energy and Environmental Design (LEED) Accredited Professional by the United States Green Building Council. He is among the first lawyers in Raleigh to be designated a LEED Accredited Professional. 
In 2013, 2014, 2015 and 2016, Jamie was recognized as a North Carolina "Rising Star" in the area of Real Estate by SuperLawyers magazine. He was also selected to the 2016 Legal Elite list for Real Estate by Business North Carolina magazine. During law school, Mr. McCaskill participated in the Jessup International Moot Court Competition, placing second in the Southeast.

University of Alabama School of Law, J.D. magna cum laude 
University of North Carolina at Chapel Hill, B.S.B.A.


Representative Matters:

Of note, Jamie has represented a student housing development and management company in the purchase of multiple college and university student housing projects across the county totaling approximately $500 million in value, assisted the owner and operator of multiple senior living facilities in the development, acquisition and licensing of Continuing Care Retirement Centers and served as local North Carolina counsel to a large Washington D.C. based a real estate private equity fund on a number of acquisition and development projects.