James C. McCaskill

Jamie McCaskill is the Managing Partner of Longleaf Law Partners, a leading boutique commercial real estate law firm based in Raleigh, NC.

Jamie focuses his practice on commercial real estate, representing clients in a broad variety of matters, including the acquisition, disposition, financing, development, leasing and management of real property across all asset classes throughout the United States.

He has represented clients with transactions worth billions of dollars in the areas of student housing, senior living, hotels and large mixed-used development projects. 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.

With extensive experience handling legal matters related to capital markets and commercial financing, Jamie routinely represents community banks, as well as national banking organizations and large credit unions. He has advised clients on multiple real estate-backed commercial loan originations collateralized by assets located throughout the country.

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.

Jamie also serves as an adjunct professor at UNC’s Kenan-Flagler Business School.

Education

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

Representative Transactions

• Represented a student housing development and management company in the purchase of multiple college and university student housing projects across the county, totaling more than $1 billion in value.
• Assisted the owner and operator of multiple senior living facilities in the development, acquisition and licensing of Continuing Care Retirement Centers.