NHL star Evander Kane said in judicial papers filed last week that he wagered sometimes as often as 50 times a day, which is in large part why he filed for Chapter 11 bankruptcy with liabilities topping $26 million.

Kane’s post-trial brief, in the lawsuit brought by his biggest creditor, Centennial Bank, laid out the player’s family background and tried to explain how that played a part in his spiraling debt in spite of overall career earnings that have reached $76 million.

“Kane was raised on the east side of Vancouver, which at the time was a lower-class area of the city,” the post-trial brief reads. “His mother Sheri was a stay-at-home mother when Kane and his sisters were growing up because they could not afford daycare.”

“Kane was drafted by his first team when he was seventeen years old, and he began playing professional hockey straight out of high school at the age of eighteen,” his lawyers wrote in the post-trial brief, which the judge requested after the trial, which took place on Jan. 23 and 25. “He has never taken any college or college-level courses, nor any courses or training about accounting, money management, or business development (and the NHL does not provide any financial education to its players). Although Kane became a highly compensated athlete in his fourteen-year career, he was raised in a working-class family that never owned a home, struggled financially, and lived month-to-month.”

One of Centennial’s arguments is that Kane was sloppy in record keeping and cannot provide documentation for much of what he claims. The bankruptcy law requires debtors to keep thorough records but makes allowances for those not considered sophisticated. 

The missing paperwork includes details on Kane’s gambling losses, which he revealed for the first time is the principal reason he lost so much money. He points to the start of his gambling “addiction,” for which the brief maintains he is in counseling, as starting in 2012 when he signed his first big contract in the NHL with the Winnipeg Jets. But the timing proved poor because of a lockout. 

According to his trial testimony recounted in the trial brief, he found himself struggling and with no way to support his family as he’d pledged.

“After the NHL entered its lockout in 2012, Kane was uncertain about his future, how he was going to support himself and his family, and how he was going to stay current on his bills,” the post-trial brief reads. “He ‘viewed gambling as a way to make money quick,’” the brief continued, directly quoting him from the trial.

Drew Hawkins, who provides financial education programs for athletes, said while the numbers are bigger in Kane’s storyline, the theme is similar to multiple other cases of athletes’ financial woes. These players spring from disadvantaged upbringings, have no financial education, surround themselves with poor advisers, and often get into gambling, he said.

“Many of these players come from very humble backgrounds, and means that their parents or the individuals that are around them have not had any experience in dealing with this,” Hawkins said. “These guys are just left to their own and trying to figure it out. And, you know, unfortunately, they don’t get to the point where they do that … and so you end up with these horror stories of individuals going into extreme debt based on spending or based on gambling.”

Kane testified that most of his gambling losses were with bookies and was largely undocumented. The websites they had him gamble through don’t exist anymore, his brief explained.

“Documentation regarding Kane’s interactions with the bookies is harder to come by because, due to their legal status, bookies operate in a manner designed to elude record-keeping,” his trial brief said. “Kane provided a thorough explanation of his use of bookies for gambling and the systems utilized by them. He explained that he placed bets with bookies through websites and that the website addresses and his login information would automatically change every two to six months (up to 50 bets per day during Kane’s peak usage). … When Kane was down, he would pay the bookies with cash or by wire transfer, cashier’s check, bank draft, or even with jewelry.” He paid off, for example, $75,000 of bookie debt with two Rolex watches.

Centennial Bank remains unconvinced, arguing in its own post-trial brief that the Edmonton Oilers winger should not be allowed to use undocumented claims of gambling losses as a way to explain away his debt. The bank added he should have subpoenaed his bookies, and the casinos he lost money at. The bank contends that as Kane can’t account for his losses, he should not be able to complete Chapter 11 and walk away from his debts, calling the bid “shocking.”

“While the issue of gambling permeated Kane’s testimony elicited by his counsel, Kane not only lacks corroborating documentation but does not actually commit to testifying that he lost all of his assets gambling,” the bank’s brief argues.

Kane borrowed $50 million between 2014 and 2019, initially to pay off a gambling debt and other expenses, and then also to pay off previous loans. In all, he borrowed 26 times from institutional lenders, and seven times from individuals, including more than $1.1 million from two men his trial brief described as “middlemen” for bookies, Mike Lispti and Pete Gianakas.

Many of the loans were set up by Sure Sports, which arranges borrowings for athletes. The bankruptcy trustee in a separate action is suing Sure Sports over its role in Kane’s situation. A hearing, in that case, is scheduled for May 25. 

Centennial has tried previously to have the bankruptcy court block Chapter 11 and has been denied. Whether the evidence the bank presented at the trial is enough to convince the judge is not certain.  Several of Kane’s other large creditors, including Zions Bancorp., settled their cases with Kane, leaving only Centennial and Hope Parker seeking to block the Chapter 11.

Parker alleges Kane owes her more than $2 million as part of an agreement to abort her pregnancy. She is a co-plaintiff in the Centennial case, but did not bring any witnesses at the trial or file her own post-trial brief. If Chapter 11 is approved, Kane would likely be able to walk away from her claims. She filed a lawsuit against him in 2018, which is currently stayed in California state court.

Hawkins, whose company Edyoucore stages financial planning seminars for athletes, said he wonders what kind of due diligence Centennial performed on Kane. While saying he did not want to point fingers, he questioned how Kane could keep getting loan after loan.

“In a case where have you had an individual that has done this level of borrowing to try to repay back the losses that he’s had, I’ve not seen one, anywhere near the degree that has taken place here,” he said. “If an athlete came to me and said, ‘Hey, you know, I’m looking for money, these have been my challenges in terms of where my money has gone.’ I would have wanted to have a clearer idea what had perpetuated this problem. And if it was deemed that it might have been around gambling or something like that it would have given me a lot of apprehension as a lender.”

(Photo: Jess Rapfogel / Getty Images)