Overview

Brent has devoted more than 30 years to advising banks, thrifts, insurance companies and agencies, securities broker dealers, and investment advisory clients on complex regulatory matters, formation and capitalization, business combinations, examination, and enforcement issues. Brent is a strong advocate for his clients, dedicated to achieving reasonable and practical solutions.

Brent’s experience is focused on the financial services industry. He began his career as an examiner with the Office of Thrift Supervision, where he also worked as a financial analyst and fraud investigator. After law school, Brent rose to senior regulatory counsel in the law department of the Federal Reserve Bank of Chicago, advising supervisory staff on complex regulatory and supervisory matters.

Brent's practice includes representation of a wide variety of financial institutions, including insurance companies and agencies, securities broker-dealers, investment advisers, hedge funds, and other private equity funds, as well as banks and bank holding companies. He advises these entities on matters such as formation, capital restructuring, mergers, acquisitions, and other business combinations as well as regulatory matters affecting such institutions, including capital requirements, licensing, registration, and examination and enforcement issues.

Brent has served as an adjunct professor of banking law at Chicago Kent College of Law since 2004.

Credentials

Admissions

  • State of Illinois
  • State of Indiana

Education

  • Indiana University School of Law, J.D., 1993
  • Ball State University, Honors College, B.S., 1987

Experience

  • Representation of numerous financial institutions in merger and acquisition transactions.
  • Represents financial services industry professionals in disciplinary matters and administrative enforcement proceedings.
  • Represented First Busey Corporation (Nasdaq: BUSE), in its definitive agreement to acquire Investors’ Security Trust Company.
  • Represented multiple sponsors in their formation of and capital raising for private investment funds, investment advisory, regulatory, and corporate matters for such funds, including, hedge funds, managed futures funds, commodity pools, and private equity funds.
  • Acted as legal counsel to QCR Holdings, Inc. (Nasdaq: QCRH) in connection with its acquisition of Bates Financial Advisors, Inc., Bates Financial Services, Inc., Bates Securities, Inc., and Bates Financial Group, Inc.
  • Assisted numerous clients with regulatory examination issues and negotiated more than 100 enforcement actions. Represented many troubled banks regarding insolvency and potential receivership issues.
  • Represented H.F. Gehant Bancorp, Inc. in its definitive merger agreement with Tri-County Financial Group, Inc. (OTCQX: TYFG), in which Tri-County acquired its subsidiary H.F. Gehant Banking Co.
  • Represented American Enterprise Bank in entering into a definitive agreement with Northbrook Bank & Trust Company, a subsidiary of Wintrust Financial Corporation (Nasdaq: WTFC), in which Northbrook Bank & Trust Company acquired certain assets and assumed certain liabilities of American Enterprise Bank.

Newsroom

Publications

Recognitions

  • Best Lawyer, The Best Lawyers in America© (2025)
    • Securities Regulation
  • bl_mccauley2025

Organizations

  • Adjunct Professor, Banking Law and Regulation, Chicago-Kent College of Law (2007-Present)
  • Member, Financial Institutions Committee, Chicago Bar Association
    • Chairman (2005-2006)
  • Member, Association of Certified Fraud Examiners
  • Member, Risk Management Association, Chicago Chapter
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