James C. McCaskill

Firm: Longleaf Law Partners
Location: Raleigh - NC

  • 2235 Gateway Access Point Suite 201
    Raleigh, NC 27607
  • Tel : (919) 645-4318
  • Fax : (919) 510-6802

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. 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 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, 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

  • Real Estate Investment Law
  • Commercial Real Estate Development
  • Real Estate Leasing & Financing
  • Distressed Debt & Workouts

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 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.
  • Advised large Washington, D.C.-based a real estate private equity fund on a number of acquisition and development projects


  • Premier Real Estate Lawyers Exclusive Featured Attorney for Raleigh NC (2020)
  • North Carolina Super Lawyers (2013-2018)
  • Business North Carolina’s Legal Elite in Real Estate (2016, 2018)
  • Jessup International Moot Court Competition, 2nd Place in Southeast


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


Longleaf Law Partners

Longleaf Law Partners is a boutique law firm focused on commercial real estate law. Our practice is comprised of experienced attorneys who made the decision to leave large, multi-specialty firms to be part of something different. Different in how we focus our expertise, work as a team, and engage with our clients.

As a highly skilled, collaborative and resourceful team, we are the opposite of a mega-firm trying to be all things to all clients. We concentrate our practice in commercial real estate law, and the size of our firm makes us nimble and efficient.

Our attorneys assist clients with all aspects of commercial real estate, including acquisitions and dispositions, title matters, land use, development, leasing, financing, restructuring and litigation. Each attorney on our team concentrates in one or more of these areas of practice, and we work collaboratively to best represent each client. Pooling our combined skills gives our clients a powerhouse commercial real estate legal team. They benefit from our extensive knowledge of the business and financial issues underlying their transactions, as well as our understanding of the market.

We are also different in the way we interact with clients. Our attorneys are real people, down-to-earth in how we communicate and connect. As a result, our clients have come to trust us and consider us part of their larger team.

We represent some heavy-hitters – entrepreneurial real estate developers and individual investors, financial institutions, nonprofits, private equity funds, and public and private companies owning and operating real estate. We often hear from these clients how much they appreciate our big firm experience and our small firm attitude.

Our attorneys draw on our decades of practical experience and strong industry relationships to provide thoughtful and principled commercial real estate legal services. At the same time, we practice client-centered problem-solving, exploring new ways to put deals together and making efficient use of technology and resources. We maintain a lean operational and organizational infrastructure to deliver the highest quality legal services – efficiently and at a reasonable cost.

We are committed to a new model of legal practice for the next generation, and we’d like to get to know you. We invite you to explore our practice areas, then contact us to discuss how Longleaf Law Partners can strengthen your position in commercial real estate.