He owned a four-bedroom house with a pool in a ritzy York Mills neighbourhood and enjoyed all the perks of the affluent: winters luxuriating at his family’s two-storey beachfront condo in Palm Beach, idyllic summers at an island cottage in Parry Sound, a ski chalet, a golf club membership and so many trips to Las Vegas, he was on a first-name basis with casino executives.

Cash wasn’t just his nickname, it defined him; he came from money and his own annual earnings topped $400,000.

Michael (Cash) Pomer even had some prominence in Toronto, certainly within the city’s gambling community, due to his frequent appearances on television and radio as an NFL handicapper. In the ’90s and early 2000s, he could be seen trading quips with Jim Tatti on Sportsline or heard on The Fan on Sunday mornings, hosting his own two-hour gambling show.

Now the money, and some $6 million in assets, are gone. All of it.

Cash Pomer is penniless.

Even if you don’t recall Pomer as a quirky on-air personality, his is a remarkable story of loss; a tale of how the grip of drug addiction can cause a man who seemingly had everything to squander it all.

But it is also a story for which Pomer — with the help of some loyal but exasperated friends — is trying to write a final, redemptive chapter.

At 60, after a lifetime of careening from one dependency to another, Pomer is trying to rebuild his life and be an inspiration to other addicts.

The Star met Pomer several times through the spring and summer, interviews framed around a rehab stint at a Toronto treatment centre. It was his fourth try at becoming clean and sober but, this time, he believes he might be giving himself a chance.

“I haven’t gone this long without drugs or booze in my life, since I was 17,” he said, six weeks out of rehab and emanating a hopefulness that was once as absent as his wealth.

“I feel great. I’m getting my swagger back. I learned the tools (to stay sober). I didn’t care before. You’ve got to want it, plain and simple. I want it.”

Pomer once lived the high life as the charming, fun-loving epicentre of every party. And if there wasn’t a party, he’d make his own. Opioid painkillers and a few rocks of crack cocaine always took him where he wanted to be.

But when he first sat down with a Star reporter in May to share his story, it was a gambit by a desperate man flailing for a quick remedy to a complicated situation. Pomer was living on welfare and his application and subsequent appeal for disability support had both been rejected. He’d also been cut off by a private social service that had been helping.

Five months behind in his rent and just days before eviction from his North York apartment, he hoped exposing his dependencies to the world might elicit sympathy and that could, in turn, lead to public support. Friends, though skeptical of this latest Pomer scheme, offered to establish a GoFundMe web page.

At that first meeting, the former broadcaster seemed distracted. He would drift to the next story before the first was completed; the details often muddled. Over lunch at a North York diner — a meal Pomer said was, other than some fruit, his first in three days — he outlined how he had gone from gadabout to down and out. He then asked if he could order a bacon burger to go. That way he’d have something to eat the next day.

When Pomer walked there was a shuffle in his stride because of an arthritic left ankle. Even sitting, he frequently shifted uncomfortably due to chronic back pain. Anger roiled just below the surface.

After rehab, however, Pomer seemed a different person. His grey pallor was gone. He was more focused, remembering details of his life quickly and clearly. Pomer was less agitated, less beaten down, less bitter. He said he was no longer interested in applying for disability. He wanted to find work. He said he is getting control of his life. He joked often.

The primary motivation for sharing his story now, he said, was in hopes it might encourage other addicts to seek treatment or talk to their family doctor.

It was a remarkable transformation especially when you consider the heights from which Pomer had fallen.

“How many people have everything and lose everything?” wondered his childhood friend Steve Simmons.

Indeed, how does a smart, affable rich kid — the kind of free spirit who would fly his mother to Hawaii on a whim — become a broken man surviving off welfare and handouts from friends, their kindness really all that’s keeping him from living on the streets?

The high life

“I was a functioning addict,” said Pomer. “I never thought I’d end up this way but I point fingers at nobody except myself. I’m not proud of it.”

Pomer said he started using drugs the way a lot of kids did in the early ’70s, experimenting at middle school and then at York Mills Collegiate Institute, where he was on the varsity wrestling and track teams.

“Some kids smoked pot, I loved black hash,” he recalled. “I was into sports but I still liked to smoke my hash late at night. When my parents went to bed, I’d crawl out the front window, have a couple of puffs and crawl back in and go to bed.”

But while the other kids grew up to have jobs, families and mortgages, Pomer, who had girlfriends but never married, was unfettered by those day-to-day demands. He had no responsibilities and no need for self-control. His hard-driving father, who died in 1994, built a fortune through fashion retail, owning John Pomer Menswear stores and Bi-Rite outlets. At one point he had 34 stores.

Pomer’s casual drug use escalated to a dependency at some point in his 20s. Then, until he was 50, he was high virtually every day — even when he was on air.

Pomer figures he spent $3 million on recreational drugs. That number, he concedes, may be low. For years, the dependency cost him between $500 and $800 daily.

In his heyday, Pomer spent his winters in Florida golfing or hanging out with his mother. He’d fly to Tampa for his TV hits and do his radio show remotely from Palm Beach. He didn’t need a regular job, though he did work at times both for his dad and for a computer company in those early days. His engaging personality made him an excellent salesman.

So glib and charismatic was Pomer that, as a 15-year-old, he once showed up unannounced at the hotel suite of Muhammad Ali — in Toronto to do TV commentary — carrying a reel-to-reel tape recorder, and talked his way in to interview the champ.

Pomer shared his wealth and good nature and collected friends easily. Some of them — even those that disapproved of his habits — stuck with him.

Twice the Simmons family took Pomer into their home after he’d been booted out of other lodging.

“All along people have supported him,” said Sheila Simmons, Steve’s wife. “People didn’t give up on him because he was charming and fun and they remember him as this kid; this 19-year-old who was just full of piss and vinegar … there is something in him that these people feel the need to look after him.”

With those pals, in those younger years, Pomer revelled in being the fun-loving smart-ass at the centre of things.

“Then it became the late ’70s and early ’80s and all hell broke loose — that’s when cocaine really hit its peak — if you brought coke to a party and dumped it on the table, you were the coolest guy at the party,” he said.

“It was so popular, so loved, so status.”

And Pomer couldn’t resist the high it gave him.

“I enjoyed drugs. I loved drugs. I found my equilibrium in drugs,” he said. “I never blacked out. I never woke up and said, ‘Gee, I don’t remember what I did last night.’ Ever. I never had shaky hands. I never missed a show.”

Pomer’s cravings went from hash and marijuana to cocaine to painkillers to crack, with plenty of overlap and mixing and matching. It was crack cocaine, though, with its quick hit of euphoria that became his go-to.

“I enjoyed it better. It took the edge off,” he recalled. “I took a piece and crunched it up, mixed it with tobacco and rolled it in an Export paper. Put a filter in, lit it up and it was … yowser.”

Along with the crack, Pomer said there were days when he would take as many as 20 Percocets — which contain an opioid pain medication — sometimes kickstarting his morning by washing down three of them with orange juice.

So dependent was Pomer, he said his dealer would hide five days’ worth of purchases in five spots around his house. That way he could just phone his supplier to find out where that day’s stash was cached. Eventually, Pomer was making the call before breakfast. Once, when he unexpectedly decided to extend a stay at the Parry Sound cottage, his dealer made the drive north with a $2,000 supply of painkillers.

“I had a drug dealer I trusted; he never did me wrong,” said Pomer. “He bought himself a cottage and a motorcycle off me.”

A high school friend, Sheldon Jafine, believes that because Pomer came from money, there was never any motivation for him to be serious about education or career building. He did graduate from York University but his passion for sports and a knack for sports wagering put him in a position where he only had to work, Jafine figures, about 10 hours a week doing his broadcasting hits and phone line recordings. That downtime mixed with large amounts of disposal income and a lack of obligations allowed Pomer to live behind a veil of drugs.

But even as his drug use continued unabated, he managed to function in the real world. He made frequent appearances on Global-TV’s Sportsline. His football prognostications (“he was very good,” said Simmons) were a weekly fixture. He operated a popular 1-900 tout line for which punters paid $5 a minute for his football insights; some years he said that line earned him $400,000. He also had private clients to whom he’d provide gambling advice. He hosted a local charity golf tournament to raise money for an electric wheelchair sports association. The likes of former Blue Jay Buck Martinez or radio personality John Derringer stepped in to MC.

“I guess I had control of an out-of-control situation, if that makes any sense,” he said.

But while Pomer said he “loved every minute of it,” his life began to unravel. Even though he was bringing in big money, he never paid taxes. Eventually, he said, Revenue Canada came after him for $1.7 million, and he settled with a $540,000 payment. That still meant he had to sell assets, including his home, during a down market.

He got fired by The Fan in 2001 — the Globe and Mail reported he was canned for complaining on the air about the disappearance of intro music, a rights issue he’d been told not to mention — and then Sportsline was cancelled in 2006. That eroded his public profile, which dramatically hurt the popularity of his 1-900 phone line as did the growth of internet gambling websites and online wagering information.

“As I try to weave through this maze of drugging, everything came down,” he said. “I didn’t pay my taxes. I didn’t care. I didn’t give a s---. I was an idiot. I was an addict. I was irresponsible and that’s that.”

Loading... Loading... Loading... Loading... Loading... Loading...

Even his mother, Camilla, who now lives in a nursing home, sold family assets to help her son.

Jafine said another friend put it perfectly: “Every time you think Mike’s hit bottom, he finds a way to get lower.”

Pomer tried rehab three times but twice found an excuse to bail. After completing one session — paid for by a friend when he was 50 —Pomer was clean for a while and took up marathon running. A broken ankle put him back on painkillers, to which he again became addicted.

Pomer’s income eroded to a monthly welfare cheque for about $700. His rent was $1,150 a month. The math wasn’t working. Friends chipped in with some cash now and again. Or they gave him grocery store vouchers or TTC tickets, to help control how the money was being spent; sometimes, though, he’d use those vouchers to gamble on Pro-Line. A friend once gave Pomer his wife’s car but he sold it to pay rent.

While he still smoked the occasional joint, his latest dependency was alcohol. It’s what he could more readily afford. Some mornings he’d have a $2.99 breakfast at Wendy’s and then wait for the LCBO to open.

Pomer said the alcohol abuse started last year when, while working the last job he had as a clothing salesman, he got into the habit of buying a bottle after work. He soon left the job but not the booze.

“Within five minutes of getting home, the shots were being poured — vodka or Southern (Comfort). One ounce shots; I’d have four of them. Then another and another …”

Pomer said he drank almost every day for nine months — a 750-millilitre bottle would typically last two days — and on the rare day he didn’t have any booze, he’d think about how much he wanted a drink.

Jafine said Pomer was always hitting friends up for money and they started to abandon him.

“I was ready to walk from him,” said Jafine, a veterinarian who owns five animal hospitals in the Toronto area. “I told him if he didn’t go to rehab and straighten his act up and try to rebuild his life, I’m done.”

Though he pushed back, saying he didn’t need it, Pomer began a four-week rehab stint paid for by OHIP in May.

Pomer asked his landlord to delay his eviction for a few days so he could go directly to the treatment centre. He had no idea where he’d live once he got out.

Clawing back

Pomer said the counsellors viewed him as a long shot for rehab success and someone who was a master manipulator with his friends.

“As an addict, we all lie, we connive, we cheat,” said Pomer. “I don’t want to say steal but I lied a little and embellished a lot. ‘I need this for groceries.’ Well, I’ll be damned if I spent it all on groceries. I’d make sure there was a bottle, then the groceries.”

Some of his friends resent that Pomer, with his fortune gone, still maintains a sense of entitlement and an expectation that his pals will look after him.

Simmons, a newspaper sports columnist and broadcaster in Toronto, said at one point, several of Pomer’s friends put together a pool of money to cover his expenses and one of them administered it.

“What happens is, after a while, you get tired of paying because you’re not really accomplishing anything,” Simmons said. “All we were doing really was enabling.”

Once at the treatment centre, Pomer said his attitude was different from previous stints. He wanted to earn back the respect of people he cared about.

Before morning and afternoon classes — where addicts learn the 12-step program to overcome their dependencies — Pomer said he would complete the assigned reading, typically an inspirational story about someone working through trying circumstances to beat alcohol or drugs. Previously, he’d just as likely sit and read the newspaper sports section.

In the evenings, when patients go off site to attend Alcoholics Anonymous, Narcotics Anonymous or Cocaine Anonymous meetings, he said he found those gatherings captivating.

So at night, when he would normally be partying, he was now getting “a spiritual high” from guest speakers. Pomer continues to vigilantly attend meetings, often going seven nights a week and occasionally doubling up at lunchtime. He’s been asked to become a speaker at those gatherings.

Pomer is now walking 10 to13 kilometres a day and sleeping better because of it. He said he “got his skinny little legs in shape again” and he is ready to work. Pomer said his priority is to stay active. He said he did little, other than drink and watch TV, in the months leading up to rehab.

“I was just a stupid loser, isolated and feeling sorry for myself.”

Jewish Family and Child is helping, too, he said. It gave him 20 $10 gift cards for groceries and a TTC Metropass for August, which is helpful for job hunting. Pomer also reconnected with his older brother, Henry — a relationship he described as wavering between strained and estranged — and said he has been “incredibly supportive.”

Pomer hopes to eventually find an affordable basement apartment in the Bloor and Spadina area, walking distance to most of his meetings. For now he has no home and is staying with friends.

Jafine said Pomer, who rarely thought beyond his immediate desires, is finally acknowledging he needs an aftercare program. That would give him accommodation, two meals a day, counselling and drug testing for the next two or three months.

While Pomer said he didn’t go through physical withdrawal in rehab or afterwards, he did have one slip-up. One afternoon, 23 days after graduating, he bought a bottle of Southern Comfort. He took a couple of sips, and said he cursed himself and then dumped the rest down the drain. Pomer said he went back to the treatment centre, explained what had happened and received encouragement for his response.

Pomer has been looking at getting work as a waiter but as his self-confidence returns, he’s thinking about how he can use his handicapping skills again. He said he had an interview and believes he has a chance to land a job with the Ontario Lottery and Gaming Corp., working as a sports wagering adviser. He’s also going to look at trying to get back into broadcasting in some capacity.

“I don’t envy his situation, at age 60 trying to start from square one again,” said Jafine.

“But think of the alternative. If he didn’t do what he did in terms of getting help, going to rehab and trying to turn his life around, he wasn’t going to make it another five years. He was going to be homeless, in the street with nobody to help him. He would have probably died between 60 and 65.”

Pomer recently spent a day with his old friend, Steve Simmons.

“I thought it was the best I’d seen him in years, the most realistic,” said Simmons. “I just thought he was mature about what he was dealing with, which he hasn’t always been.”

“I think this probably was rock bottom for him, losing his home and going into rehab. I think it’s a pretty stunning change of life. You either deal with it and accept it or you continue on your path. It looks to me that he’s in a better place than I’ve seen in for a very long time.”

Despite being keenly aware of everything he’s lost, Pomer said he — and he knows many won’t understand this — looks back with no regrets. He remembers his “fun in the sun” with fondness.

“Most people would say, ‘C’mon, you’d take back all that money.’ No, I wouldn’t change a thing. That’s who I am. That’s who I was,” he said.

“I’m still Pomer. The only difference is, I don’t live in a big home with a pool or a tennis court or anything like that. I don’t have my Palm Beach place. I’m generous psychologically now. I listen better. I don’t have my wealth but I don’t care. I’ve been there, done that. I had my time.”