Ryan Bennett is Chair of Willkie’s Restructuring Group. He splits his time between Chicago and New York.
Ryan has more than two decades of experience guiding sophisticated corporate debtors, investors and other key parties through some of the nation’s most complex restructuring cases and transactions. He focuses on protecting and advancing the financial interests of corporate debtors and secured and unsecured creditors in the various transactional and litigation-related aspects of the debtor-creditor relationship. His clients have included public and private companies, private equity sponsors, investors, and major creditors across industries such as manufacturing, logistics, technology, automotive, hospitality, retail, and financial services.
In addition to company-side representations, Ryan regularly counsels leading private equity and investment fund clients, both in and out of court, on acquisitions of distressed assets and investments and corporate governance matters related to client portfolio companies.
Ryan also represents large, multinational corporations in distressed supply chain, acquisitions and other commercial matters involving distressed counter-parties.
Ryan has been consistently recognized by Chambers USA, The Legal 500, and Turnarounds & Workouts, among other organizations, for his industry-leading work. In the 2023–2025 editions of Chambers USA, sources noted “Ryan’s a true trusted advisor in bet-the-company matters,” “he is super skilled, incredibly accessible and knowledgeable” and “he’s extraordinarily client-oriented, extremely commercial and excellent technically.”
Experience
- Recognized in the 2023–2025 editions of Chambers USA. Sources noted “Ryan’s a true trusted advisor in bet-the-company matters,” “he is super skilled, incredibly accessible and knowledgeable” and “he’s extraordinarily client-oriented, extremely commercial and excellent technically.”
- Recognized among 500 “Leading Global Bankruptcy and Restructuring Lawyers,” Lawdragon, 2024.
- Named one of “40 Under Forty,” Chicago Daily Law Bulletin and The Chicago Lawyer, 2015.
- Recognized as a Bankruptcy “Rising Star,” Law360, 2014.
- Named an "Outstanding Young Restructuring Lawyer,” Turnarounds & Workouts, 2012.
- Chicago Learning Exchange (Board of Directors, 2022–Present)
Publications
- Contributing Editor, Norton Journal of Bankruptcy Law & Practice
- Co-author, “Chapter 11 "101" — Professional Retention and Compensation,” American Bankruptcy Institute Journal, February 2005
- Co-author, “Turning Off the Lights: Safely Shutting Down an Insolvent Subsidiary,” The Corporate Counselor, Volume 19 No. 4a, September/October 2004
- Co-author, “Chapter 11 "101" — What Every Unsecured Creditor Should Know About Chapter 11,” American Bankruptcy Institute Journal, June 2004.
- Assistant Editor, “Use, Sale or Lease of Property Under 11 U.S.C. § 363,” Norton Bankruptcy Law & Practice, West Group 2003 – 2004 editions
- Author, “Safeguards of the Republic: The Professional Responsibility of the American Lawyer to Preserve the Republic Through Law-Related Education,” Notre Dame Journal of Law, Ethics and Public Policy, 2000
Seminars
- Speaker, “The Nuts & Bolts of a First Day Hearing,” Financial Poise, April 2025
- Co-moderator, “Distressed Hedge Funds,” Wharton Restructuring and Distressed Investing Conference, New York, February 2019
- Moderator, “Sparking Transformation: Energy Restructurings,” Wharton Restructuring and Distressed Investing Conference, New York, February 2019
- Speaker, “Board Members & Insolvent Companies They Serve,” Private Directors Association, March 2017
- Speaker, “Energy Master Limited Partnerships: Eye on Sabine Oil and Gas and What Will Follow,” Essential Power Sources: Managing Energy Deals and Legal Counsel, sponsored by Bloomberg, Houston, Texas, October 2016
- Speaker, “Energy Restructuring & Bankruptcy,” Energy Law Seminar, University of Chicago Law School, May 2016
- Panelist, “Panic In Detroit: Chapter 9 Bankruptcy Process from Soup to Nuts,” American Bankruptcy Institute Annual Spring Meeting, Washington, D.C., April 2015
Energy
- Hornbeck Offshore Services, Inc. — Represented Hornbeck Offshore Services, Inc. and its affiliates, in its Chapter 11 restructuring in the United States Bankruptcy Court for the Southern District of Texas. The Hornbeck Chapter 11 cases were filed with a prepackaged plan of reorganization that contemplated a $75 million in debtor-in-possession (DIP) financing and a fully backstopped $100 million rights offering.
- Sabine Oil & Gas Corporation — Represented Texas-based Sabine Oil & Gas and its subsidiaries, an independent oil and gas exploration and production company with approximately $2.6 billion in outstanding funded debt obligations, in their Chapter 11 cases in the Southern District of New York. Notably, in the context of Sabine’s Chapter 11 case, Ryan successfully argued for Sabine’s right to reject certain midstream gathering agreements and obtained a ruling that the covenants contained in such agreements do not “run with the land” under Texas law. See In re Sabine Oil & Gas Corporation et al., 547 B.R. 66, (Bankr. S.D.N.Y. 2016). That ruling has been widely covered in the press and has since been upheld on appeal by the U.S. District Court for the Southern District of New York. In 2017, the Turnaround Management Association recognized the successful restructuring of Sabine Oil & Gas Corporation with its “Large Company Transaction of the Year Award.”
- Emerald Oil, Inc. — Represented Emerald Oil, Inc., a Denver based independent exploration and production company that is focused on acquiring acreage and developing wells in North Dakota and Montana, in Emerald's Chapter 11 cases in the U.S. Bankruptcy Court for the District of Delaware.
- Permian Holdings, Inc. — Represented Texas-based Permian Holdings, Inc., the largest U.S. manufacturer of above-ground storage and processing tanks for the oil and natural gas exploration and production industry, in connection with its stakeholder negotiations and successful out-of-court recapitalization.
- Globe Energy Services, LLC — Represented Texas-based Globe Energy, a leading provider of oilfield services, with a majority of its operations in the Permian basin, in connection with Globe’s successful lender negotiations and out-of-court recapitalization.
- Petroflow Energy, Ltd. — Represented Calgary-based Petroflow and its U.S. subsidiaries as an independent oil and gas drilling, exploration and production company, in Petroflow’s Chapter 11 reorganization in the U.S. Bankruptcy Court for the District of Delaware.
- NRG Energy, Inc. — Represented NRG Energy, a multi-billion dollar international energy services conglomerate, in connection with its Chapter 11 reorganization in the U.S. Bankruptcy Court for the Southern District of New York. Within this “mega-case”, Ryan was primarily responsible for negotiating and obtaining court approval of his client’s sale of certain non-core assets, including the $80.4 million sale of electrical turbines to a Chinese power company and the $160 million sale of a 520 mega-watt generating power facility to an Oklahoma-based energy provider. Ryan’s role included advising on the marketing and auction process; negotiating and drafting the necessary pleadings and purchase agreements; and negotiating cash collateral agreements with the client’s prepetition secured lenders.
- In addition to the above-listed public matters, Ryan has also been involved in a number of non-public, out of court workouts and negotiations representing oil and gas companies in the upstream, midstream and oilfield services sub-sectors.
Telecommunications, Media and Internet
- Sungard AS Capital, Inc. — Represented Sungard AS Capital, Inc. and its affiliates in their Chapter 11 cases in the U.S. Bankruptcy Court of the Southern District of New York, in the fastest Chapter 11 case in history. Sungard AS obtained confirmation in less than 19 hours on May 2, 2019. In addition, Sungard AS emerged from Chapter 11 faster than any company in history—staying in Chapter 11 for less than 48 hours. Sungard AS, a provider of availability and recovery services, had approximately $1.26 billion in funded debt at the commencement of its Chapter 11 cases and deleveraged by over $900 million upon emergence.
- VER Technologies HoldCo LLC — Represented VER Technologies HoldCo LLC and certain of its affiliates (collectively, “VER”) in Chapter 11 cases in the United States Bankruptcy Court for the District of Delaware. At the time the cases were filed, VER had funded debt of over $760 million. VER commenced the cases with the support of over two-thirds of the lenders under its prepetition term loan facility, the lenders under its term loan debtor-in-possession financing facility, holders of two tranches of promissory notes, and a strategic merger partner. These parties supported VER’s Chapter 11 cases pursuant to a restructuring support agreement that provided the basis for a consensual Chapter 11 plan followed immediately by a merger of the reorganized equity into the strategic partner. In 2018, the Turnaround Management Association recognized VER with its “Restructuring of the Year” (over $500M to $1bn) award.
- DBSD North America, Inc. — Represented DBSD and its subsidiaries in its Chapter 11 cases in the U.S. Bankruptcy Court for the Southern District of New York. Specifically, Ryan served as the principal attorney representing DBSD in negotiating and obtaining court approval of the $1.49 billion cash investment from DISH Network.
- Telecommunications company — Represented a leading telecommunications provider in preserving the integrity of its supply chain, including with respect to a distressed supplier and provider of semiconductor chip assemblies, in Chapter 11 cases in the U.S. Bankruptcy Court for the District of Delaware.
- Twentieth Century Fox Film Corporation — Represented Fox in its negotiations with Cinram International, Fox's primary provider and distributor of DVDs, in connection with Cinram's consensual out-of-court workout.
- Cable & Wireless (USA), Inc. — Represented Cable & Wireless, a leading Internet services provider, in drafting, negotiating, and confirming its Chapter 11 plan of liquidation in the U.S. Bankruptcy Court for the District of Delaware.
- Rogers Communications, Inc. — Represented Rogers Communications, a leading North American cable service provider, in protecting its interests as a creditor and cooperative high-speed Internet provider in the Excite@Home bankruptcy case in the U.S. Bankruptcy Court for the Northern District of California. Concurrently, Ryan also represented his client's Chief Executive Officer in such officer's capacity as a former Director of Excite@Home.
Municipal
- Syncora Holdings Ltd. — Represented Syncora Holdings Ltd. and certain of its subsidiaries in connection with the City of Detroit’s Chapter 9 case, the largest-ever municipal bankruptcy case. Syncora, through its subsidiaries, insures or holds a substantial amount of the City of Detroit’s municipal finance debt obligations. The City of Detroit has reported more than $18 billion in liabilities, approximately $9 billion of which relate to municipal finance debt obligations.
Transportation
- Accuride Corporation — Representing Accuride Corporation and 15 of its debtor affiliates in their Chapter 11 cases in the U.S. Bankruptcy Court for the District of Delaware. Accuride is the one of the largest and most diversified manufacturers and suppliers of wheels and wheel end components in the world. Accuride commenced its Chapter 11 cases with approximately $485.6 million in funded debt and commitments from an ad hoc group of prepetition term loan lenders to provide nearly $103 million in debtor-in-possession financing. Accuride and its term loan lenders have also agreed on the framework of a consensual restructuring transaction which will deleverage the company’s balance sheet via an equitization of the lenders’ prepetition debt.
- Bouchard Transportation Co., Inc. — Represented Bouchard Transportation Co., Inc. and certain of its subsidiaries (“BTC”) in their Chapter 11 cases in the United States Bankruptcy Court for the Southern District of Texas. Prior to the bankruptcy filing, BTC was one of the nation’s largest independently owned ocean-going petroleum barge companies operating within the Jones Act market, possessing a fleet of 24 barges and 25 tugs that provided oil and petroleum product transportation services. During their Chapter 11 cases, BTC obtained over $100 million of new capital through a series of court-approved transactions and consummated two simultaneous value-maximizing sale transactions for substantially all of their assets that allowed their state of the art fleet to continue operating in the Jones Act market.
- Dura Automotive Systems, LLC — Represented Dura Automotive Systems, LLC and certain of its subsidiaries (“Dura”), a leading independent designer and manufacturer of automotive systems, including mechatronic systems, exterior systems, and lightweight structural systems, in their Chapter 11 cases. At the time of the Chapter 11 filing, Dura and its affiliates had operations in thirteen countries with sales from its three main product segments generating approximately $1.1 billion in 2018.
- GST Autoleather, Inc. — Represented GST Autoleather, Inc., a supplier of leather upholstery to nearly every major automaker, in its Chapter 11 cases in the United States Bankruptcy Court for the District of Delaware. The Company obtained a commitment from its senior secured lenders for a $40 million debtor-in-possession facility, the proceeds of which will be used to fund ongoing business operations while pursuing a court-supervised going concern sale. GST has operations in North America, China, South Korea, Europe, and South Africa.
- Japan Airlines Corporation (JAL) — Represented Japan Airlines Corporation, Asia's largest air carrier with a fleet of more than 270 aircraft, as international restructuring counsel advising JAL on all aspects of the restructuring of its global operations and represented it in connection with its Chapter 15 cases. JAL, headquartered in Tokyo, maintained $28 billion in debt at the time of its filing and operated over 900 daily flights from over 60 airports in Japan and provided international flight services to 11 million international passengers in 34 countries each year.
- Lear Corporation — Represented Lear Corporation, a leading global supplier of seating and electrical systems to the automotive industry, in achieving the first successful prearranged Chapter 11 restructuring of a tier 1 automotive supplier. Both prior to and during Lear's Chapter 11 filing, Ryan worked with Lear's senior management and major creditor constituents to achieve consensus, while preserving the goodwill of Lear's customers, suppliers and employees. In just four months after filing for bankruptcy in the U.S. Bankruptcy Court for the Southern District of New York, Lear and its 23 U.S. and Canadian subsidiaries emerged from Chapter 11, having eliminated approximately $3 billion in debt, preserved the supply base and positioned the Company as a highly competitive player in its market.
- Global Aviation Holdings Inc. — Represented Global Aviation Holdings and its domestic affiliates in all aspects of its complex Chapter 11 reorganization proceedings before the United States Bankruptcy Court for the Eastern District of New York. Global Aviation, through its subsidiaries World Airways and North American Airlines, is the largest commercial provider of airlift transport services for the U.S. military. Global Aviation also provides commercial cargo and passenger charter services, most notably for the presidential campaigns of President George W. Bush, Secretary of State Hillary Clinton and President Barack Obama. Kirkland assisted Global Aviation in deleveraging its balance sheet with more than $350 million in debt, optimizing and rationalizing its aircraft fleet of approximately 30 airplanes and renegotiating competitive labor contracts with its unionized employees.
- The Boeing Company and Boeing Capital Loan Corporation — Represented Boeing, the world's leading aerospace company and the largest combined manufacturer of commercial jetliners and military aircraft, in its joint capacity as most significant customer and debtor-in-possession lender in connection with the U.S. Chapter 11 case, Section 363 sale, and related Canadian insolvency proceedings of Northstar Aerospace (USA) Inc., a supplier of components and assemblies for the commercial and military aerospace markets.
- DURA Automotive Systems, Inc. — Represented DURA Automotive, an international tier 1 automotive supplier, and forty-one of its domestic and Canadian subsidiaries, in connection with their highly consensual and successful Chapter 11 reorganization cases in the U.S. Bankruptcy Court for the District of Delaware. Among his responsibilities, Ryan managed the day-to-day administration of the Chapter 11 process, and represented DURA in all aspects of its complex multi-billion dollar restructuring.
- Tower Automotive, Inc. — Represented Tower Automotive, a leading tier 1 automotive supplier, in connection with its successful Chapter 11 reorganization case in the U.S. Bankruptcy Court for the Southern District of New York. Among his responsibilities on this case, Ryan was principally charged with maintaining and ensuring the integrity of Tower's supply chain. In this context, he frequently negotiated trade and pricing agreements with Tower's vendors and customers, developed business and litigation tactics to counter stop shipment threats by sole-source vendors, and obtained court approval of several commercial initiatives designed to improve Tower's North American business model.
- MPI International, Inc. — Represented MPI International, a global and specialized automotive supplier, as the largest unsecured creditor and chair of the Official Committee of Unsecured Creditors, in the Chapter 11 bankruptcy case of Sturgis Iron & Metal Co., Inc., in the U.S. Bankruptcy Court for the Western District of Michigan.
- Atlantic Equity Partners, L.P. (AEP) — Represented AEP in its capacity as prepetition secured lender and proposed Chapter 11 plan sponsor in the Chapter 11 cases of BHM Technologies Holdings, Inc. et al., pending in the U.S. Bankruptcy Court for the Western District of Michigan.
- In addition to the above-listed public matters, Ryan has also actively participated on both debtor and creditor sides in several out of court workouts, restructurings, and consensual wind-downs of various "tier 1" and "tier 2" automotive suppliers.
International
- Betcorp Ltd. — Represented the Australian liquidating trustee of Betcorp Ltd., a former Internet gaming company, in filing its petition for recognition under the newly-established Chapter 15 of the U.S. Bankruptcy Code, in the U.S. Bankruptcy Court for the District of Nevada. Betcorp's petition was highly contested, but the Bankruptcy Court ultimately ruled in Ryan's client's favor, recognizing the Australian liquidation as a "foreign main proceeding" under Chapter 15. The Court issued and published a 27-page opinion on the ruling, which has been frequently cited in subsequent bankruptcy court opinions and publications. See In re Betcorp Ltd., 400 B.R. 266 (Bankr. D. Nev. 2009).
- Cover-All Holding Corp. — Represented Cover-All Holding Corp. and its ten Canadian and U.S. subsidiaries, as the once leading global manufacturers of pre-engineered building structures, in successfully obtaining an order pursuant to Chapter 15 of the U.S. Bankruptcy Code recognizing the Cover-All debtors' case under the Canadian Creditors Companies Arrangement Act (CCAA) as a foreign main proceeding. The Cover-All companies were the first foreign debtors to obtain Chapter 15 recognition in the U.S. Bankruptcy Court for the Eastern District of Pennsylvania.
Industrial (Non-Transportation)
- Archer-Daniels-Midland Company (ADM) — Represented ADM as the stalking horse bidder and successful purchaser of substantially all of the industrial and grain facility assets formerly owned by Wisconsin-based Olsen Brothers Enterprises, L.P. ADM's $49.7 million acquisition was approved, in part, pursuant to a confirmed creditor-sponsored Chapter 11 plan, in the U.S. Bankruptcy Court for the Eastern District of Wisconsin.
- Atwood Mobile Products, Inc. — Represented Atwood, a prominent manufacturer of components for the recreational and specialty vehicle industry, with respect to its Chapter 11 bankruptcy case in the U.S. Bankruptcy Court for the District of Delaware, and subsequent $160 million going-concern sale to Insight Equity, pursuant to section 363 of the Bankruptcy Code.
- J&L Specialty Steel, Inc. — Represented J&L Specialty Steel, a leading North American manufacturer of flat rolled stainless steel, in its successful out of court restructuring and ultimate acquisition by Allegheny Ludlum Corporation.
- W.R. Grace & Co. — Represented W.R. Grace, an international chemical supply conglomerate, in connection with preparing and negotiating its Chapter 11 plan of reorganization in the U.S. Bankruptcy Court for the District of Delaware.
- National Equipment Services, Inc. — Represented National Equipment Services (n/k/a NES Rentals), a national equipment leasing corporation, in all aspects of its Chapter 11 reorganization in the U.S. Bankruptcy Court for the Northern District of Illinois.
- Polymer Group, Inc. — Represented Polymer Group, a large industrial manufacturer, in all aspects of its restructuring efforts both prior to, and within the context of, a Chapter 11 reorganization in the U.S. Bankruptcy Court for the District of South Carolina.
Real Estate Development & Hospitality
- Heartland Food Corp. — Represented Heartland Food Corp., one of the largest Burger King franchisees in the U.S., as the stalking horse bidder for, and successful purchaser of, the restaurant franchise of Duke & King Acquisition Corp., in a Section 363 sale, before the U.S. Bankruptcy Court for the District of Minnesota.
- Clark Realty Capital — Represented Clark Realty with respect to identifying and analyzing distressed real estate investment and development opportunities.
- Global Hyatt Corporation — Represented Hyatt in connection with its interests as a significant creditor and contract counterparty of the Cosmopolitan Resort in Las Vegas, Nevada.
- Global private investment firm — Represented a private investment firm focused on real estate in connection with analysis and potential acquisitions of distressed properties.
Healthcare, Retail and Consumer Services
- Prima® Wawona — Represented Prima® Wawona and certain of its affiliates in their Chapter 11 cases in the United States Bankruptcy Court for the District of Delaware. Prima®, then the largest producer of stone fruit in the United States, entered Chapter 11 in October 2023 to address its approximately $1 billion total debt load. Pursuant to Prima®’s confirmed Chapter 11 plan, Prima® consummated an equitization transaction that transitioned ownership of Prima®’s real estate owning entity to its “PropCo” secured lenders and the ownership of its operating assets to a liquidating trust for the benefit of its “OpCo” secured lenders, and effectuated a global settlement among Prima®’s lenders, creditors and former equity stakeholders.
- Invacare Corporation — Represented Invacare Corporation and its subsidiaries in their prearranged Chapter 11 cases filed in the U.S. Bankruptcy Court for the Southern District of Texas. Invacare, a manufacturer and distributor of innovative medical equipment for use in home healthcare, retail and extended care markets worldwide, emerged from bankruptcy on May 5, 2023, just over three months after filing for Chapter 11. Through the Chapter 11 cases, Invacare was able to discharge approximately $300 million in funded-debt obligations and unsecured liabilities, raise $75 million of new equity capital, secure $40 million of exit financing, and position its business for long-term success.
- Carlson Travel, Inc. — Represented Carlson Travel, Inc. and 37 of its affiliates (“CWT”) in the fastest cross-border prepackaged restructuring transaction to date. On November 12, 2021, the U.S. Bankruptcy Court for the Southern District of Texas entered an order confirming CWT’s prepackaged Chapter 11 plan of reorganization, just 18 hours after commencing bankruptcy proceedings. CWT is a leader in business travel management with over 12,000 employees and operations in 140 countries and territories around the world. As a result of the restructuring, CWT eliminated almost $900 million of its $1.6 billion of debt, secured access to $775 million of exit facilities and a $350 million equity investment, and preserved the entirety of its worldwide employee base.
- Post Acute Medical, LLC — Represented Post-Acute Medical, LLC (“PAM”), as stalking horse bidder and ultimate purchaser of nine long-term acute care hospitals from LifeCare Holdings LLC and its affiliates (“LifeCare”). The sale was approved in LifeCare’s Chapter 11 cases in the Bankruptcy Court for the District of Delaware following an auction. PAM provides post-acute health care services at over 40 long-term acute care hospitals and inpatient rehabilitation hospitals and over 30 outpatient physical therapy locations.
- InSight Health Services Corp. — Represented InSight Health Services Holdings Corp. and its 16 subsidiaries, a leading provider of diagnostic imaging services, in connection with InSight's prepackaged Chapter 11 cases in the U.S. Bankruptcy Court for the Southern District of New York.
- Westcliff Medical Laboratories, Inc. — Represented Westcliff and its parent, BioLabs, Inc., in connection with their Section 363 going concern asset sale to Laboratory Corporation of America (LabCorp) in the U.S. Bankruptcy Court for the Central District of California.
- Boyds Collection, Ltd. — Represented Boyds, a leading designer, manufacturer and distributor of hand-crafted collectibles and gift products, in drafting, negotiating, and confirming its Chapter 11 plan of reorganization in the U.S. Bankruptcy Court for the District of Maryland.
- Quality Stores, Inc. — Represented Quality Stores, a large retail chain, as a debtor in its Chapter 11 liquidation proceedings in the U.S. Bankruptcy Court for the Western District of Michigan.
*Ryan advised on some of these matters prior to joining Willkie.
Credentials
Education
Notre Dame Law School, J.D., 2000 Michigan State University, B.A., 1996
Bar Admissions
Court Admissions
United States District Court, Northern District of Illinois United States Court of Appeals, 7th Circuit United States District Court, Western District of Michigan United States Court of Appeals, Federal Circuit United States District Court, Eastern District of Michigan United States Supreme Court United States District Court, Eastern District of Wisconsin