Cynthia A. Bergmann


[email protected]

Phone: (312) 360-6652

Fax: (312) 360-6520

As a former in-house counsel, I know that the most important skill I bring to any client relationship is the ability to put myself in the shoes of my clients –understanding their business and helping them achieve the best business solutions for their issues. This type of approach is an integral part of our culture at Freeborn.



Cindy Bergmann is a Partner, Leader of the Transportation Industry Practice Team, Co-Leader of the Corporate Practice Group and former Chair of the Firm’s Executive Committee.

She focuses her practice on the legal and business affairs of public and private companies, including mergers and acquisitions, financing, real estate and general corporate matters. Cindy assists large and mid-size corporations with the acquisition and sale of subsidiaries, joint ventures, development of new facilities and strategic initiatives, with a special focus on the transportation industry. She also has extensive experience in all aspects of commercial finance and real estate.

Cindy's finance practice includes representing borrowers and lenders in a broad range of financing transactions, including secured, real estate and construction loans, subordinated debt and equipment lease transactions, as well as representing borrowers and lenders in loan enforcement and workout matters. Cindy’s real estate practice includes representing clients in the acquisition, development, construction, leasing and sale of office, industrial and residential real estate.

Before joining Freeborn, she was U.S. Corporate Counsel for Canadian National Railroad where she managed all legal aspects of U.S. corporate, real estate and financial matters, including mergers and acquisitions, corporate governance, the acquisition and development of new facilities, the disposition of surplus assets, financing transactions, equipment leases, credit policy and bankruptcy management.

Representative Matters

Representative Matters

  • Represented Canada's largest freight railroad and intermodal transportation provider's purchase of a railroad operating in the suburbs surrounding Chicago, from a major integrated steel producer. 

  • Represented a private equity lender in providing DIP financing for a cable television operation, including warrant grants, clawback rights, PIK interest and complex FCC issues.

  • Represented a Canadian corporation and its U.S. subsidiaries in a $1 billion master credit facility from a consortium of Canadian and U.S. lenders.

  • Represented lenders and borrowers, including tenant-in-common investor groups, in numerous loan workout transactions, including the restructuring of debt for steel mills, paper mills, real estate developments and manufacturing entities.

  • Represented an ESOP borrower in the refinancing of an $85 million senior, secured-term and revolving debt facility from a syndicate of lenders.

  • Handled all aspects of the acquisition, development and construction of a 250-acre industrial facility joint venture.

  • Closed numerous railcar, locomotive, aircraft and vessel lease financing transactions.

  • Represented both lenders and developers in connection with the development and sale of industrial parks and facilities.

  • Acted as lead counsel for a Class 1 Railroad in connection with the $380 million acquisition of three railroads and a vessel transportation company.

  • Represented a major North American railroad company in $40 million acquisition of a Michigan-based short-line railroad operator.

  • Represented a major North American railroad company in the acquisition of a majority interest in a privately held railroad and transloading business for $18 million.

  • Represented large family office as lead investor in global PE / VC funds, including relating to fund agreements, side letters, co-investments and ancillary agreements and matters.

Honors & Awards

Honors & Awards

  • Illinois Leading Lawyers - 2020 (cited in multiple years)

Professional Activities

Professional Activities

  • Immediate Past President, Association of Transportation Law Professionals
  • ABA Construction Industry Forum
  • Traffic Club of Chicago
  • American Shortline & Regional Railroad Association General Counsel Committee
  • Transportation Lawyers Association