NEW YORK CITY — Callaway Arts & Entertainment, Inc. filed for Chapter 11 bankruptcy protection last week. The New York City-based company estimated both its assets and its liabilities at between $1 million and $10 million in court papers.

The company owes more than $4 million to its 20 largest unsecured creditors, according to court filings. Among those creditors are Bob Dylan, who is owed $450,000, and Hachette Book Group, which is owed nearly $1.7 million. The bankruptcy petition does not specify the nature of the debts it owes to unsecured creditors.

During the COVID-19 pandemic, the company's traditional funding sources, including retail banks, reduced loan issuance compared to previous levels, according to court filings. The company turned to alternate lenders with financing terms that the CEO described as predatory, and the cost of those loans continues to adversely affect its business.

Toper Taylor, who owns 15% of the company, is its sole secured creditor, according to court filings. The company has published several hundred titles in its more than 40-year history.

The company has produced Madonna's 1992 "Sex" book and her children's book series. The company also produced a Sistine Chapel book trilogy priced at $25,000. Its most recent collaboration was with The Bob Dylan Center to produce the 2023 book "Bob Dylan: Mixing Up the Medicine," which is about the working life of Bob Dylan, an 84-year-old Grammy-winning singer-songwriter. The company generated over $100 million in retail sales in seven years, according to the CEO's declaration in court filings.