From Madonna photo ops to bankruptcy: the publisher that owes Bob Dylan blames 'predatory' lenders

• Callaway Arts & Entertainment, Inc. has filed for Chapter 11 bankruptcy protection.
• The publishing company that owes Bob Dylan six figures blamed "predatory" lenders.
• The company has produced Madonna's 1992 "Sex" book and her children's book series.

A high-end book publisher that owes hundreds of thousands of dollars to music legend Bob Dylan is blaming "predatory" lenders for pushing it into bankruptcy.

Callaway Arts & Entertainment, Inc., a decades-old New York City-based multimedia publishing company known for producing illustrated books, including Madonna's 1992 "Sex" book and the singer's children's book series, filed for Chapter 11 bankruptcy protection last week.

The company, which was also behind a $25,000 Sistine Chapel book trilogy, has estimated both its assets and liabilities at between $1 million and $10 million in court papers.

In a Monday court filing, founder and CEO Nicholas Callaway pointed to past backing from late Apple founder Steve Jobs as he outlined the company's path to bankruptcy.

He wrote that in 2000, he met Jobs, "who was so impressed with Callaway's work that he helped arrange Debtor with project financing by Kleiner Perkins to produce some of Apple's first mobile & tablet apps."

Callaway wrote that his company's projects can each take years to develop, making financing "key" to its business model.

When the COVID-19 pandemic hit, the company's traditional funding sources "dried up," Callaway wrote, noting that retail banks "were not issuing loans as they had in the past."

As a result, the company was "forced to turn to predatory alternate lenders," the CEO wrote, adding that the "cost of doing so continues to adversely affect" the business. The court papers did not detail who those lenders are.

Facing ongoing cash flow issues, the company turned to Chapter 11 to reorganize its debts and business, Callaway wrote.

Court papers show that Toper Taylor, an entrepreneur with a 15% ownership of the company, is Callaway's sole secured creditor, putting him ahead of unsecured creditors for repayment in the bankruptcy.

Separate court filings show that the publishing company owes more than $4 million to its 20 largest unsecured creditors, including $450,000 to Dylan and nearly $1.7 million to Hachette Book Group, one of the biggest publishers in the country.

In the Monday court filing, the CEO described the company as a publisher of "ultra high-quality books for renowned artists" like Madonna, Georgia O'Keeffe, and Dylan. "Each published work is a piece of art in and of itself," Callaway wrote.

The CEO said that the company's "most recent notable collaboration" was with The Bob Dylan Center to produce 2023 book, "Bob Dylan: Mixing Up the Medicine," about the working life of the now-84-year-old Grammy-winning singer-songwriter.

"The 608-page tome spans his life from childhood in Minnesota through his entire career," Callaway wrote. "It took seven years of close collaboration to produce this work which includes 30 original essays and more than 1,100 images by 135 artists."

The company's bankruptcy petition does not specify the nature of the debts it owes to unsecured creditors like Dylan.

In his declaration, the CEO said that his company has published several hundred titles in its more than 40-year history and generated over $100 million in retail sales in seven years.