500 West Madison Street Suite 3700, Chicago, IL USA 60661
Brett Winterstein focuses his practice on mergers and acquisitions, venture capital transactions, growth equity transactions and loan transactions, with an emphasis on middle-market transactions. Brett’s clients include, among others, food and beverage companies, trucking and logistics companies, telecommunication companies, technology start-ups, including software companies, domestic and international manufacturers, travel and leisure companies and commercial banks. Additionally, Brett routinely advises venture capital funds, growth equity funds, independent sponsors, family offices and private equity funds.
In addition to his transactional practice, Brett serves middle-market businesses nationwide as outside general counsel, advising on a range of business matters, including corporate formation and governance, equity issuances, commercial contracting and employment matters. Prior to joining the firm, Brett was a partner and Chair of the Business and Finance Group at HMB Legal Counsel, a well-established, corporate-focused law firm based in Chicago, Illinois.
Clients call on Brett to help them grow, diversify and monetize their businesses. He prides himself on being available 24/7 and providing sound, practical advice.
Brett was recognized as an Illinois “Rising Star” in 2019 and 2020 for Mergers and Acquisitions by Super Lawyers magazine and played a crucial role in Kilpatrick’s Corporate/M&A and Private Equity – Illinois group becoming Chambers ranked in 2025.
Experience
Mergers and Acquisitions
Represented Project Management Advisors (“PMA”) in connection with its partnership with Brailsford & Dunlavey, a national real estate advisory and program management firm headquartered in Washington, D.C. The partnership expands PMA’s capabilities in strategic planning, project leadership, owner’s representation, and operations consulting for social and institutional infrastructure clients and large asset owners, while adding national reach and enhanced sector expertise.
Represented Mexpress Transportation, Inc., a provider of cross-border freight transportation services between the U.S. and Mexico, on its partnership with Energy Transport Logistics, via its financial sponsors EVE Partners, Northwood Ventures, Ocean Avenue Capital Partners, Tin Goose Partners, HighVista Strategies, and Apogem Capital.
Represented Middleton Partners on its partnership with Bevan Cellars, a leading Napa Valley winery offering highly-rated wines across both accessible and highly limited, single-vineyard, ultra-premium price points.
Represented Benton Technical Services, Inc., a national leader in aerial and underground telecommunication construction, on its partnership with Triage Partners, via its financial sponsors, Broadtree Partners, Mars Equity Partners and TPE Boulder. By adding construction to Triage Partners’ portfolio, Triage Partners can now truly act as a one-stop partner supporting projects from start to finish with the same quality and commitment that its customers already know it for.
Represented HTL Freight, fast-growing third-party logistics (3PL) company, in its acquisition of TS3 Logistics, a California-based freight brokerage with specialized expertise in temperature-controlled and LTL reefer transportation. This acquisition marks a strategic step in the HTL Freight’s expansion into high-value, niche logistics services and broader geographic coverage.
Served as US counsel to MyVenue, Inc. (“MyVenue”), a worldwide leader in event venue point-of-sale technology, on its partnership with family office and growth equity firm, Greater Sum Ventures. The funding will provide MyVenue additional capital and specialized resources to accelerate global growth and R&D initiatives.
Represented Bosworth Capital Partners on its partnership with Dynamic Rubber LLC, a leading manufacturer of inflatable seals and rubber products intended to serve various industries, including aerospace, auto manufacturing, chemical manufacturing, medical, and others.
Represented ID Label, Inc. (“ID Label”), an industry leader in variable information barcode labels and warehouse signage, on its partnership with River Associates Investments, L.P. This strategic partnership will enhance ID Label's capabilities and market reach, while maintaining the ID Label brand.
Represented Horwitz, LLC (“Horwitz”), a Midwest-based mechanical, electrical, and plumbing (MEP) specialty contractor, in its acquisition of Preferred Electric, an established electrical contractor specializing in commercial and industrial sectors. This acquisition is a critical step in Horwitz’s strategy to become a more comprehensive specialty service provider, significantly enhancing its ability to meet the evolving needs of both current and future clients.
Represented Hartwig Mechanical Inc., on its partnership with Crete United. Since 1958, Hartwig has become one of the most reliable full-service mechanical firms in the Midwest. Its partnership with Crete will broaden its services to include plumbing, alongside its established HVAC and electrical capabilities and extend its operational reach to Northern Illinois, the North Side of Chicago and Southern Wisconsin.
Represented Svoboda Capital Partners, on its partnership with Axiom Advisors Group, LLC. Axiom is one of California’s leading and fastest-growing government relations and public affairs firms. Its partnership with Svoboda will enable Axiom to sustain its growth trajectory, by re-investing in its current team members and valued clients while exponentially expanding personnel and issue expertise, as well as coverage to additional California markets.
Represented Northeast Contracting Corp. ("NECC"), on its partnership with RCap Equity Partners ("RCap"). NECC is a full-service commercial roofing business focused on replacement, maintenance, and new installation. It operates within the mid-Atlantic and serves a variety of end markets, including education, government, multi-family, and industrial. With RCap's support, NECC will continue to invest in its team, expand its service offerings and footprint, and pursue strategic acquisitions.
Represented Kiddleton, Inc., a subsidiary of GENDA Group, with the purchase of 100% of the equity interests in National Entertainment Network (NEN). NEN is one of the largest amusement and vending operators in the U.S. with over 30,000 cranes and bulk vending machines.
Represented Svoboda Capital Partners, on its partnership with Highdive Advertising, LLC. Highdive operates as a creative-first advertising agency specializing in the strategy, development, and delivery of high-profile marketing campaigns for prominent brands. Highdive provides a fully integrated service offering, primarily providing strategic, creative, and production services, across a variety of advertising channels, including digital, TV, print, earned activations, and more.
*Represented BestRX, a leading pharmacy management software company, on its successful sale to RedSail Technologies, a strategic buyer backed by Francisco Partners.
*Represented Craftable, the hospitality industry’s leading SaaS platform, on its partnership with Gauge Capital, a leading middle-market private equity firm based in Dallas, Texas. This strategic investment further enhances Craftable’s position at the forefront of cutting edge technology shaping the hospitality industry.
*Represented Bully Pulpit Interactive, a strategic communications and public affairs agency, on its investment from Broad Sky Partners. BPI is an outcomes agency at the intersection of business, politics and policy. Through Broad Sky’s network, industry expertise, and robust value creation capabilities, the firm aims to help BPI expand its services base and enter new markets organically and through M&A. The investment will also support further development of proprietary platforms to measure impact and the growth of BPI’s employee base as the agency continues to build momentum on its industry-leading talent advantage.
Venture Capital Transactions and Growth Equity Transactions
*Represented Swag Golf in $10,000,000 growth equity investment by Verance Capital. The investment is intended to bolster Swag Golf’s innovative product lines, increase its presence in the Asia-Pacific market and accelerate its production capabilities to meet growing demand.
Lending Transactions
Represented commercial bank in $275,000,000 loan to professional sports team.
Represented contract manufacturing company in $200,000,000+ loan from commercial bank.
*Experience gained by attorney prior to joining Kilpatrick
Insights View All
Entrepreneurship Through Acquisition-Search Funds
Venture Capital and Emerging Companies
Joint Ventures & Strategic Alliances
Washington University School of Law J.D. (2009)
University of Maryland B.A. (2005)
Illinois (2011)
New York (2010)
Jewish Council for Youth Services, Board of Directors, Alumni
Northmoor Country Club. Legal Committee, Member
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