In 2017, then-San Jose Sharks forward Evander Kane owed $140,000 to a bookie who went by the pseudonym “Vinny,” and $100,000 to a casino, some of the tens of millions of dollars of debt that Kane, who filed for Chapter 7 bankruptcy protection early last year, accumulated over his career. To make the payments, and others, he frequently borrowed from friends and scores of lenders.

These details emerged in a court motion last week by his top creditor, Centennial Bank, which wants to block the bankruptcy to prevent Kane from walking away from his debts. The bank, which claims it is owed more than $8 million, included with its motion excerpts of a July deposition in which Kane outlined a history of borrowing tens of millions of dollars to pay off loans and other debts, including to bookies.

Centennial is trying to get to the heart of one of the most high-profile athlete bankruptcy cases in years: with over $50 million of career earnings and tens of millions of dollars of borrowings, what happened to the money? “I’m just trying to figure out what exactly, what you’ve done with your funds,” a Centennial lawyer asked Kane early on in the bankruptcy proceedings, during what is known as a 2004 examination, excerpts of which were attached to the bank’s motion.

It doesn’t appear Centennial, which declined to comment through one of its lawyers, yet has an answer.

When Kane, who now plays for the Edmonton Oilers, filed his petition nearly two years ago, he listed assets of $10.2 million and debts of $26.8 million, much of it recently borrowed bank debt. But between 2014 and 2018, Kane also borrowed almost $30 million in 16 separate transactions detailed in the declaration of Centennial lawyer Andrew Ghekas, with the proceeds often used to pay down or retire previous loans.

In the bank’s motion, the lender writes that since 2014, Kane has entered 24 separate lending arrangements.

“It was a cycle of just taking out new loans to pay off existing loans,” Kane said, in the July 6 deposition, according to the partial transcript included as an exhibit to Centennial’s motion. And referring to the financial firm he retained to arrange the debt, Kane added, “Sure Sports were the ones that were seeking these loans out for me, they were the ones that sought out the loan with you and Centennial Bank, and it was just a vicious cycle of loan after loan that they were able to get me into.”