Aaron May is respected by clients for his ability to distill complex, high-stakes real estate issues into clear, actionable strategies. Known for his sharp analysis and practical approach, Aaron brings a rare combination of breadth and depth to his practice. High-net-worth real estate investors, developers, operators and lenders rely on him for guidance in structuring sophisticated, tax-efficient transactions across a wide range of asset classes and deal types.
As Vice Chair of the firm’s Real Estate Practice, Aaron advises clients in all aspects of commercial real estate transactions nationwide. His work includes the acquisition, financing, development and leasing of office, industrial, retail, mixed-use and residential properties. He has represented the owners of some of Chicago’s most iconic commercial buildings, including the Old Post Office and Aon Center, and is widely sought after for his experience in tax-driven deals, including complex 1031 “like-kind” exchanges, REIT transactions and joint ventures.
His experience includes:
- Acquisition and sale of office, retail and industrial properties
- Financing transactions
- Office and retail leasing
- Telecommunications site transactions
- Land use and development
Aaron has been involved in hundreds of leasing transactions, ranging from ground leases for nationwide developments to multimillion-dollar deals in major downtown office towers. He frequently advises clients on tax-focused structuring, including representation of high net-worth real estate investors in sophisticated, tax-sensitive transactions. Recent professional highlights include:
- Represented investors in the contribution of a nearly $100 million multi-property real estate portfolio to a publicly traded REIT via “Down REIT” transaction.
- Represented the sellers in a $64 million multi-property portfolio sale of triple-net leased real estate assets.
- Represented a telecommunications company in a multi-site, sale-leaseback transaction, including drafting and negotiating sale documents and corresponding leaseback agreements.
- Represented a real estate investor in the acquisition of an $18 million medical office building, including assumption of senior and subordinated debt.
- Represented real estate investors in dozens of 1031 “like-kind” exchanges and related acquisition, sale and financing transactions.
- Represented a real estate investor in a $23 million office building sale through 1031 “like-kind” exchange and corresponding acquisition of 230,000-square-foot industrial building, including negotiation of purchase and sale agreements, financing documents, and related long-term, triple-net lease.
- Represented a real estate investor in the acquisition of property subject to long-term, triple-net office and retail leases, including negotiation of the purchase and sale agreement, lease amendments and acquisition loan documents, as well as review of corresponding subdivision documents.
- Represented mid-sized lender in numerous commercial term and construction loan transactions.
Aaron is an active member of ULI Chicago and serves on the Finance Committee of Saint Viator High School. He is a member of both the American and Chicago Bar Associations. Outside of work, Aaron enjoys playing basketball and golf.
