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Cumulus Media’s SDTX Filing Is 2026’s Eighth Billion-Dollar Bankruptcy; Delaware Has Yet to Record 2026 $1B+ Chapter 11

Legal Analysis: Jessica Steinhagen

The week’s chapter 11s were all freefalls, except for “audio-first” media company Cumulus Media Inc., which emerged from a previous chapter 11 process less than eight years ago and is pursuing a prepackaged case in the Southern District of Texas that would deleverage the company by approximately $529 million and position it for “future strategic opportunities.” Cumulus was also the largest case this week, filing with $1 billion to $10 billion in liabilities on its petition, approximately $700 million of which is funded debt.

The next largest filer was Hawthorne Race Course, which reported $100 million to $500 million in liabilities and operates a horse race track and network of off-track betting venues. The company filed to reorganize after complications from a $1.5 million judgment entered in favor of Churchill Downs.

StopLoss, an emergency response and property restoration services provider, is also looking to reorganize and restart operations after an alleged breach of a factoring agreement that resulted in loss of its job to restore the Renaissance Tower in Dallas. Mirror Lake Village LLC is likewise looking to reorganize its senior living community near Tacoma, Wash. Tech-enabled healthcare practice Nava Health MD, which filed after repercussions from a failed merger, says its consolidated health and wellness business has an “established” customer base of patients to sustain operations.

Allstate Lending Group Inc. filed after being embroiled in a federal lawsuit alleging that it engaged in a “years-long pattern of fraudulent conduct” in originating, pooling and selling fractionalized interests in secured real estate loans to individuals and entities. RAD Diversified REIT Inc. is also facing litigation along with regulatory actions, including from the Florida attorney general who has said the company “appears to be a Ponzi scheme.”

The rest of the week’s cases, making up the majority, were also real estate-related cases, including from real estate developer Lurin, which is looking to sell three multifamily residential properties located in Houston, Fort Walton Beach, Fla. and Pensacola, Fla.

Texas, which accounts for about 9% of the country’s population, currently makes up 22% of all chapter 11s filed by non-real estate debtors with more than $10 million in liabilities over the last 12 months. While states like Texas and Delaware are expected to host disproportionately higher shares of chapter 11 cases relative to population based on their statuses as prime bankruptcy court venues, Texas’ share is high even in the $10 million to $100 million range, for which patterns regarding jurisdictions are far less established. In 2026, for this smaller range, Delaware accounts for only 4%, California accounts for 16%, and Texas and Florida each account for 14%.

Real estate is excluded from the graph above due to the $10 million liability threshold. Since most real estate debtors file single asset real estate chapter 11s, their likelihood of filing is linked directly to geographies where real estate values are particularly high, like New York and California. Nonetheless, several states have become more consistently active in this bankruptcy space, including Colorado, Georgia and New Jersey.

Atlanta-based Cumulus Media Inc. commenced a prepackaged chapter 11 case on Wednesday in the Southern District of Texas, pursuant to a restructuring support agreement with an ad hoc group of funded debtholders. The debtors intend to fund their cases, at least initially, through the consensual use of cash collateral, saying they have approximately $46 million cash on hand. The disclosure statement, however, notes that the debtors may obtain DIP financing, which would be secured by priming liens junior to the ABL liens.

Cumulus primarily attributes its business struggles to “sustained challenges in the broadcast radio industry and broader macroeconomic pressures” that “reduced advertising demand and constrained liquidity.” Those macroeconomic pressures include “competition from digital audio and streaming platforms” and “persistent inflation.”

At Thursday’s first day hearing, Judge Alfredo Perez granted all of the first day relief on an uncontested basis. Debtors’ counsel said that the debtors run a radio business, and radio is “challenging” and facing “incredible headwinds.” Debtors’ counsel explained that consumers are migrating away from radio to Spotify and Apple Music, and the pandemic also changed people’s mobility patterns. Now that more people are working remotely, counsel added, fewer people are driving to the office, which means less revenue from radio ads.

Cumulus is the year’s eighth chapter 11 to file with more than $1 billion in liabilities, making 2026 the quickest of the last nine years to reach this level.

Cumulus’ prior chapter 11 case was filed in the Southern District of New York, and this week’s “chapter 22” filing was commenced in the Southern District of Texas. Two months and five days into the year, there are still no billion-dollar filings in the SDNY or Delaware, with New Jersey currently leading:

RAD Diversified REIT Inc., a Port Richey, Fla.-based real estate investment trust focused on the acquisition of residential real property, filed on Sunday in the Middle District of Florida. The debtors own more than 300 residential rental properties and vacant residential lots located predominantly in Pennsylvania, Texas and Florida, and filed chapter 11 in the face of regulatory actions and dozens of pending foreclosures. The company is subject to regulatory actions by the U.S. Securities and Exchange Commission and the Florida attorney general.

Nava Health MD, a “vertically integrated, tech-enabled healthcare practice combining integrative, functional, preventive, and regenerative medicine,” filed on Sunday in the Eastern District of Virginia. The debtors have four locations in Virginia and Maryland. The company sought to go public in 2024 through a blank check merger with 99 Acquisition Group, valued at $320 million, but the merger failed to close. The merger would have provided up to $20 million to the debtors.

In anticipation of the merger, the company began expansion efforts in 2024 and signed at least 16 new leases, commenced construction of retail locations and took out bridge lending. When the merger failed, Nava was left with “massive” obligations it was unable to pay. The company abandoned commercial leases, did not pay construction costs and let its bridge loan go into default, leading to “cascading financial problems and deficiencies in existing business operations.” Nonetheless, the debtors say that their consolidated health and wellness business has an “established” customer base of patients to sustain operations.

Hawthorne Race Course, a Stickney, Ill.-based horse race track and network of off-track betting venues filed on Feb. 27 in the Northern District of Illinois. The company is looking to sell assets as a going-concern or alternatively sell physical assets. The debtors say that reorganization is possible to restart operations if they can reach agreement on a recapitalization “as part of a plan process for resolving the Debtors’ other liabilities.”

In December 2025, a $1.5 million judgment against the debtors was entered by an Illinois state court in favor of Churchill Downs and on Feb. 3, a “Citation to Discover Assets” was issued to Hawthorne. Due to the citation, the debtors have not been able to use their revenue stream and senior secured lender Signature Bank has not been willing to fund operational expenses. The company seeks to fund the case with a $16 million DIP financing facility from third-party JDI Loans LLC.

Mirror Lake Village LLC, a senior living community in Federal Way, Wash., near Tacoma, filed on Feb. 27 in the Western District of Washington after secured lender Northwest Bank initiated foreclosure proceedings and sought appointment of a receiver. Northwest Bank’s $17 million was set to mature in July 2025, but the lender refused to negotiate an extension due to insufficient operating income and high vacancy rates. JingHu LLC, a holding company that owns a portion of the debtor’s equity, has offered up to $2.5 million in DIP financing.

StopLoss, an Alpharetta, Ga.-based emergency response and property restoration services provider, filed for chapter 11 protection on March 5 in the Bankruptcy Court for the Southern District of Texas. The debtors attribute the filing to Insured Advocacy Group LLC’s alleged breach of the parties’ factoring agreement relating to the debtors’ contract to restore the Renaissance Tower in Dallas.

The debtors have a pending lawsuit against Insured Advocacy Group in the U.S. District Court for the Southern District of New York, the proceeds of which, the debtors say, would be essential to repay creditors and restart operations. The debtors received a $5.75 million DIP financing term sheet that is under negotiation, while the debtors look for other potential DIP lenders. The debtors are also bidding for new jobs for which the company will need new capital.

Below is a list of single asset real estate cases from the week, in lieu of an individual filing alert:

Case Name/Petition Court Address
Iron Mountain
Holdings LLC
W.D. Texas 5000 Bell Springs, Dripping Springs, Texas
(valued at $1 million according to petition)
Express Stores Inc.
dba Boney Joes
S.D. Texas 100 S. Hwy 174, Rio Vista, Texas
1925 Belt Line Road LLC E.D. Texas 1925 Belt Line Rd., Carrollton, Texas
539 Huron Real Estate Co. E.D. Mich. 539 & 569 South Huron St., Ypsilanti, Mich.
Avalon Derm
Realty LLC
E.D.N.Y. 55 Greene Ave. 2D and 2E, Brooklyn, NY
(each valued at $1 million according petition)
MelPro LLC D.C. 501 Mellon St. SE, Washington DC
(valued at $1.5 million according to petition)
99A Somers LLC E.D.N.Y. 99A Somers St., Brooklyn NY
Mazala HB LLC C.D. Calif. 20042 Beach Blvd., Huntington Beach, Calif.
400 South Boston LLC N.D. Okla. 400 South Boston, Tulsa, Okla. (“Debtor believes
the true property value to be something less than
$5.5M. Marketability will be hindered because of
a lack of parking (which is currently being
provided free of charge by another entity).
Property Value as given by Tulsa Assessor is
$7.1M,” according to petition)
30-85 31st Property LLC E.D.N.Y. 1834 127th St., College Point, NY

Below is a recap of this week’s sale-related events for the week’s cases:

RAD Diversified REIT
RAD Diversified REIT is a real estate investment trust focused on residential properties.
Debtors say they expect to sell some properties.
Hawthorne Race Course
Hawthorne Race Course operates a horse racing and wagering business.
The company is looking to sell assets as a going-concern or alternatively sell physical assets.
An August 2025 appraisal values the race course property at $95 million (only for the land, less demolition costs to remove existing buildings). An April 2025 appraisal shows the debtors’ Crestwood, Ill. property at $3.2 million.

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