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His tears fell on the sidewalk

as he stumbled in the street

a dozen people stopped to stare

but no one stopped to speak.

For his castle was a hallway, and

the bottle was his friend…’

Gordon Lightfoot


       The cold wind blew through the canyons of the city on an overcast April morning.   A man stood shivering on the street corner, sipping from a cup of Tim Horton’s coffee.  He had purchased it with a few coins left from yesterday’s panhandling.  Earlier, he had left the homeless shelter in time to be at Union Station to meet the arriving GO Train crowd.  Among the herd of rushing commuters, there were always a few kind souls who would drop coins into his hat.  He stood there with a dazed look, holding a cardboard sign which read Homeless & Hungry.  His coat was tattered and threadbare. He was bearded and the exposed part of his face was bright red from exposure to the elements.  The poor man was bone thin, but it wasn’t hunger that was driving him.  He was badly in need of money to buy a bottle of vodka at the liquor store.    

     His hands shook as he counted the coins accumulated in his hat.  He thought, not bad, but not enough!  The man decided to walk uptown to a more productive location on Bay Street in the financial district.  It was a place largely inhabited by bankers and stock brokers, and some of them could be very generous.  The next hour of begging for money was a total bust.  He was starting to feel desperate and briefly considered stealing a bottle from the liquor store.  He knew that the government run LCBO had recently adopted a policy of not confronting shoplifters, and now many thieves and deadbeats were having a field day walking away with pilfered booze.  His whole mental focus was on the means of getting a drink.  He looked up from where he sat as several well-dressed men approached.  Most of them averted their eyes, but one of the men said, “God bless,” and dropped a twenty dollar bill into his hat.

     The man guzzled the last remains of the vodka and set the bottle down on the bench beside him.  He was sitting in a bus shelter, seeking to escape the wind and light rain that was now falling.  Earlier a security guard had rousted him from the hallway of a nearby building and he had stumbled around drunkenly until he found cover.   Fortified by drink he didn’t feel the cold so much, although his jacket was totally soaked through.  A woman looked at him through the glass with disgust, preferring to wait out in the rain than to share the shelter with him.  It was late afternoon and he hadn’t eaten a thing all day.  He left the bus shelter and paused furtively to urinate in the outer foyer of a theatre.  A passing police car braked and the driver briefly sounded the shrill siren.  As the officer stepped out of the vehicle, the homeless man hurriedly retreated up the street.

     He saw a young woman striding towards him.  She had blonde hair and magnificent long legs, her feet sheathed in red high heeled shoes.  She was the most beautiful creature he had ever seen.  The woman saw him looming drunkenly on the sidewalk and attempted to avoid him by crossing the street, but the traffic was too busy.  As she approached, he gave her a wide toothless grin.  She turned away in revulsion and hurried past, her red shoes tapping a staccato beat on the sidewalk.  He felt no shame or sense of rejection from her dismissal.  He was a hollowed out man, dazed and devoid of any of the redeeming qualities he once had.  His only thought was about finding his next drink.  He turned when he heard the rattle of a grocery cart.  It was being pushed by a man he had met recently at the homeless shelter.  The man stopped and said, “Hey Jack, what’s happening?”

      John W. Stedman, aka Jack, as his friend had called him, was reeling drunk and feeling a little dizzy.  Still, he agreed to walk with the other man to the soup kitchen up on Richmond Street.  The place served food, cafeteria style and there were long tables where you could sit and eat.  When they arrived there was already a long line-up outside of the building.  There was a certain amount of banter and jostling going on, but Jack had learned to keep his mouth shut and not make eye contact with other homeless men.  He knew that the addictions, mental illness and desperation prominent amongst this group was a volatile mixture that could ignite at any time.  Recently he had been involved in a violent altercation at the homeless shelter.  He was fuzzy on the details.  All he knew when he woke-up the following morning was that he was missing two front teeth.

     Later they walked over to the Good Shepherd Homeless Shelter and attempted to secure a bed for the night.  Unfortunately it was already filled to capacity and they were turned away.  During the next hour they visited two other shelters and got the same story.  It was dark by then, and it looked as if they would be spending the night huddled under a bridge or on a park bench.  Jack’s friend had a sleeping bag in the grocery cart and so was much better equipped.  Eventually they parted company and Jack headed down towards Union Station where he hoped to hang out for a while in a place where it was warm and dry, at least until the security people chased him away.  Jack had just crossed Front Street when a fancy looking car pulled up to the curb.  He wondered, is that a Rolls-Royce?  The passenger side window was lowered and a man motioned for him to approach.


     Jack Stedman had always been described by his friends as being somewhat tightly wrapped, but he managed to blunt his natural impatience and high energy with a determined physical fitness regime.  This began in high school where he competed in track and field, and continued through his university years when he started running marathons.  In later years, this evolved into Iron Man competitions.  The time he Jack allotted to these activities did not interfere with his dedication to his studies, nor to later pursuits in his professional life.  He graduated with an MSc degree from McGill University, where he also perfected his ability to speak the French language.  He obtained a job in the aeronautical industry, first as an analyst and later in marketing and development.  Finally, he found his niche selling jet aircraft to well-healed corporate executives.

     Jack met his wife Cynthia at McGill University where she was studying for an arts degree.  The two met at an off campus pub and quickly became an item.  They were crazy about each other, although Jack’s friends would observe that Cynthia’s assertive type-A personality didn’t exactly provide a calming Ying, to Jack’s hard-driving Yang.  Nevertheless, they became inseparable.  Prior to graduating, a corporate head hunter had recruited Jack for a job with the Boeing Company in Richmond, British Columbia.  Cynthia still had two years remaining in her studies, but rather than be separated by such a great distance, she decided to drop out of McGill and they were married in a hasty civil ceremony.  This impulsive compromise on her part would eventually haunt them in the form of regrets and incrimination.

     The first few years of their marriage were happy ones. They bought a house in the Fulton Hill area of Richmond, and Cynthia resumed part time studies at the Vancouver campus of UBC.  Jack was absorbed with his new job at Boeing, and was quickly recognized for his potential in sales and marketing.  Everything was going swimmingly until the day Cynthia discovered that she was pregnant.  This unplanned event led to some adjustments, and once again Cynthia compromised by putting her academic studies on hold.  It was a very difficult pregnancy for her, and when the baby was delivered stillborn, Cynthia fell into a deep postpartum depression.  As they both grieved for the lost child, Jack’s escape was to focus more on his work. This caused a strain in their relationship, and being denied the emotional support that she needed, Cynthia began to drink.

     Over the next few years their relationship became more strained and the couple drifted further apart.  Jack was travelling extensively for work, and in his absence Cynthia resumed part- time studies at the university.  She found much needed acceptance among a group of new friends, and soon began an affair with a handsome young student.  It was an intense physical relationship centered on partying, drinking and the occasional drug use.   Cynthia and Jack argued over her frequent unexplained absences, and this came to a head one evening when she was arrested for driving under the influence.  Her blood alcohol concentration was over twice the legal limit and this resulted in an automatic 90 day suspension of her driver’s licence.  Later in court, the suspension was extended to a full year.  Cynthia was now pretty much confined to their suburban home, a considerable distance away from her new friends and studies.  She fell into yet another deep depression.  

     Things went from bad to worse as Cynthia’s drinking increased, and Jack began to hit the bottle pretty hard himself.  In an effort to repair their relationship, they agreed to go to couple’s therapy.  The psychologist led them through a series of questions to which there were no easy answers.  They could find no common ground, and Cynthia in particular found it difficult to suppress her pent-up frustration and anger.  In the end, the therapy served as a neutral forum where they could talk about their feelings, but it provided no pathway to reconciliation.  They gave it up after a few sessions.  A week later, Cynthia had an Uber driver pick up a bottle of vodka at the liquor store.  That evening, in an intoxicated state, she swallowed a fist full of Prozac pills and slipped into a hot bath.  That is where Jack found her the next day when he returned from a business trip.  

     Jack was totally unravelled, and unable to cope with the guilt he felt over Cynthia’s death.  His escape was the bottle, and this had some unpleasant consequences.  He was called up on the carpet on two occasions at work, and finally written up with a stern warning that his behavior was unacceptable.  After Boeing finally terminated his employment, Jack had a total nervous breakdown and went on a multi-day bender.  When he finally surfaced, he decided to sell the house and move away to escape the bad memories.  He liquidated his assets and moved to a high-end apartment complex in downtown Vancouver.  Over the next two years he existed in a drunken haze.  He lived lavishly and spent his money recklessly on a series of lady friends.  In the end, Jack was flat broke, and with his final few dollars he bought a bus ticket to Toronto.  When he arrived he was at rock bottom, and soon became just another homeless man on the streets.


     Richard Meriwether stepped up to reception at the Fairmont Banff Springs Hotel and demanded, “Give me your best room, mon!”  The desk clerk had been alerted to this special guest’s imminent arrival, and had already pre-registered him in one of the exclusive Turret Suites.  He said, “Certainly, sir,” and without further-adieu handed Meriwether a welcome package and summoned a bellman.  As the guest was being guided to the elevator, a voice shouted out, “Hey Richie, welcome to the conference.” Richard turned as one of his arch rivals approached from across the lobby.  Tim Monahan was a top producer with a bank owned brokerage house, one with whom he had gone head-to-head on past occasions competing for prospective clients.  The two men were friendly, but circumspect about each another’s intentions.  They shook hands and agreed to meet later in the bar for a drink.

     Meriwether entered his suite and found it adorned with fresh flowers and a bottle of ice cold champagne.  He popped the cork, poured a glass and then read a welcome note from the conference host.  It was a three-day affair sponsored by a major mutual fund company.  The agenda included a helicopter tour, a golf tournament, black tie reception and even a presentation by a renowned guest speaker, the former U.S. President Bill Clinton.  This fund company lavished every conceivable perk on its top sales supporters, and Richard Meriwether was their number one producer.  He wasn’t particularly well liked by other financial advisors, who found him to be arrogant and braggadocios.  But, they were in awe of his success and treated him almost with reverence.  Amongst this crowd Richard was the big swinging dick, and he played his role to the hilt with flashy jewelry, seven thousand dollar Tom Ford suits and driving a Rolls-Royce Phantom automobile.

     Richard’s dark complexion and facial features reflected the mixed ancestry to which he boasted.  Originally from Jamaica, he made the exaggerated claim that his forefathers included a Scottish laird and a Senegalese chieftain.  He had immigrated to Canada as a teenager, but had never lost his distinguishing Jamaican accent.  After labouring in a series of minor sales jobs, he had graduated to becoming a Dale Carnegie instructor.  Always a hustler and fast talker, his mantra was fake it til you make it.  Later, after he entered the financial services industry, his personality and aggressive sales ability led to amazing success.  No longer faking it, he had become a millionaire many times over.  He would say to prospective clients with absolute conviction, “Come with me, mon.  Get on the program … I make you rich!” 


     His style of investing was to ‘buy and hold,’ often leveraging his clients with borrowed money.  He recommended mutual funds as the vehicle for building long term wealth, and combined this with a variety of tax shelters which were appealing to his high net worth clients.  Richard eschewed the typical stock broker’s method of designing individual portfolios.  He disdainfully referred to competitors like Tim Monahan as ‘stock jockeys,’ and told anyone who would listen that these guys picked stocks by throwing darts at the business pages.  He also made the erroneous claim that they were all commission hounds who churned their client’s portfolios to generate revenue.  Richard insisted that success in investing resulted from time in the market, not timing the market, and that investing shouldn’t be played like a game of Snakes & Ladders.  Another of his oft-used adages was that your investment portfolio was like a bar of soap, and the more you handled, it the smaller it got.

On day two of the conference, Richard and Tim met for a drink in the elegant Rundle Bar.  Both men were hugely successful in their respective realms, and widely recognized in the investment community.  As usual, the topic of conversation centered on the economy, interest rates and the potential for growing their businesses.  They were having a second drink when Richard said, “Tim, come and work with me.  I make you rich.”  Tim thought, what an arrogant prick.  He laughed and said, “I’m doing pretty well where I am, thanks.”  Richard pulled something from his pocket and laid it on the table.  It was a laminated copy of his T4 slip, showing a net taxable income of almost four million dollars.   Tim was impressed by the number, but thought, this guy’s ego is monumental!  He explained to Richard that he and his team had over three quarters of a billion dollars of client assets under administration, and they were growing rapidly.

     As the discussion continued, the verbal fencing became more aggressive.  Both men were supremely confident in their personal and professional abilities and respective approach to the business.  At one point Richard called Tim a ‘stock jockey.’  Tim countered by saying he had heard that some of Richard’s tax shelters had imploded and that his clients had received margin calls.  Richard pointed to the disaster of Nortel and a few other unfortunate hiccups that had vaporized some client’s portfolios.  Richard went a step too far when he suggested that a monkey could be trained to do what Tim does.  This led to more bitter words, and then a challenge was introduced.  Richard said he was prepared to bet one million dollars that he could find some homeless drunk, and in six months train him sufficiently that he could be hired by a major wealth management firm.   Tim stuck out his hand and said, “You’re on!”


     The bet was on, but it would be subject to both parties agreeing to a suitable candidate.  Also, it was to remain a secret between the two of them, and in no way could their respective firms or any compliance body become aware of it.  The definition of success – or a win - for Richard would be for the candidate to acquire the entry level accreditations and be hired by a major wealth management firm within six months.  Tim suggested that he might have someone in mind.  He told Richard about the pan-handler he saw every morning at Union Station.  The two men agreed to check the guy out upon returning to Toronto.  Several days later, they were on the platform to meet the morning GO Train, and scoped out a man who was holding a sign which read, Homeless & Hungry.  The guy was a pathetic looking burnout, and appeared to be either mentally challenged or under the influence.  

     Tim asked, “So, what do you think?”  Richard responded, “This guys a damned basket case!  You’d be totally stacking the deck in your favor.”  Tim smiled and said, “Hey, you said you could train a monkey to do my job.”  They discreetly observed the man for a while, and then followed him up to Bay Street.  They watched as a well-dressed businessman dropped some money into the guy’s hat. A few minutes later he got up, and they tailed him to a nearby liquor store.  The man came out carrying a paper bag, and then proceeded to walk around occasionally sipping from the lip of a concealed bottle.   An hour later they grew weary of the surveillance. They were both anxious to get the project under way, so in the end Richard agreed to accept the guy, so long as they could convince him to come on board.  He said that he would make the approach later that evening. 


     Richard and Tim were both financially well off, and this bet was more about the thrill of the competition than it was for monetary gain.   For Richard in particular, it was all about proving that he was right, so he could throw it in his competitor’s face. He also thought, what a great story to tell prospective clients!  Later that night, he pulled up to the curb on Front Street and lowered the passenger side window.  He leaned over and gestured for the homeless man to approach.  Jack halted a few paces from the car, as some black dude stuck his head out and said, “Come with me, mon.”  Jack immediately thought, this guy wants a blow-job.  He said, “Screw you.” Richard smoothly responded that he just wanted to help out.  He pleaded, “Come with me, we’ll have a few drinks and a bite to eat.” He opened the car door, and after a brief pause Jack cautiously entered.  Richard almost gagged from the man’s body odor as they pulled away in the Rolls-Royce Phantom. 

     Ten minutes later they pulled up to valet parking at the St. Regis Hotel, where Richard had reserved a suite.  He slipped a C-note to the attendant and said, “Take good care of my ride, and don’t pull any of that Ferris Bueller shit.”  Jack was in a daze as they passed through the revolving doors and walked across the opulent marble lobby to the front desk.  The clerk’s eyes almost popped out as she looked upon them in astonishment.  Richard dropped his American Express Centurion Black Card on the counter and said, “My name is Meriwether and I’ve reserved the grand deluxe suite. Make this quick, and then send the butler up to our room.” After the bellman had escorted them to the suite, Richard called room service and ordered two jumbo shrimp cocktails and a bottle of champagne.  A few minutes later the butler arrived at the door.  He said, “Good evening, Sir.  How may I be of service?”

     Jack was still in a daze as he listened to Richard issue instructions to the butler.  His head pounded from the bottle of vodka he had consumed earlier, and he had absolutely no clue about where he was or what was going on.  After room service arrived, his new friend poured two glasses of champagne, and they sat at a table and nibbled on some shrimp.  It was the tastiest food he’d had for a long time, and the ice cold champagne seemed to soothe his headache and bring his mind back into focus.  The man said, “I’m your guardian angel, mon.”  He went on to explain that he was rescuing Jack from the streets, and had a wonderful employment opportunity for him.  Finally, he led Jack to the bathroom and told him to take a shower.  Jack thought, oh shit, here we go! But, the guy just closed the door and left him there alone.  He emerged half an hour later, freshly scrubbed, wearing a thick terrycloth robe.  His own clothing had mysteriously disappeared.

     The next morning there was a knock on the door and a room service attendant rolled in a breakfast trolley.  Along with the food there was a Bloody Mary for Jack, which Richard had ordered as a preventative hair of the dog to mollify his alcoholic protégé.  He explained that they had a busy schedule that morning, prior to catching a flight to where he would begin training for his new job.  Richard mentioned that he had removed Jack’s passport and other ID from his soiled clothing the previous evening, before disposing of it.  Jack was totally bewildered, but he gulped his drink and decided to just go with the flow.  A short time later a man from King & Bay Custom Clothing arrived with a basic ensemble for Jack, including undergarments, socks, shoes and a leather travel bag.  Then it was off to a nearby salon where Jack had a hair-cut and beard trim.  That afternoon Richard drove them to the Toronto Airport, and escorted Jack to the departure gate.


     Osgood Meriwether stood in the arrivals area of the Montego Bay terminal, holding a sign with Jack’s name.  Finally from amongst the crowd of tourists a man approached and said, “Hi, I’m Jack.” Ossie’s first thought was, dis is some mashed up fella.  The guy looked like he had been shot out of a cannon!  His eyes were all bloodshot and he had a terribly sick look about him.  Ossie took the man’s bag and said, “Welcome to Jamaica, mon.”  Jack asked, “Is there anywhere we can get a drink?”  A few minutes later they were in the terminal bar sipping Red Stripe beers.  Ossie explained that his brother Richie had charged him with training Jack into good physical condition.  They would be staying at the family farm in St. Elizabeth Parish, which was about a two hour’s drive to the south.  He frowned and added, “Dis be your last drink for a long while.”

     The Meriwether’s lived on a small one hectare farm located between the Black River and the nearby Santa Cruz mountains.  The house was modest, but well maintained as were the outbuildings and surrounding fields.  Chickens scattered in the yard as they pulled up in Ozzie’s battered pickup truck.  An attractive older woman greeted them as they approached the front door.  Ozzie said, “Mamma, this is Richard’s friend Jack from Canada.”  Jack was momentarily confused as the woman was white, while Ozzie was dark skinned like his older brother.  Whatever the explanation, his only interest at the moment was where he could get a drink?  They washed up and sat at a trestle table along with two other men, who were introduced as hired hands.  The tasty dinner was rice with chicken, fresh baked bread, and a pitcher of cold milk.  Jack just poked at his food as he was a bit nauseated, and already feeling the pangs of withdrawal.


     The next two weeks were a living hell for Jack, as he suffered an anguishing withdrawal from his alcohol dependency.  He had the sweats, hallucinations and experienced a complete emotional breakdown.  Anxious and depressed, he begged, cried, became angry and finally lay in his bed in the worker’s quarters, shaking and mumbling incoherently.  When he finally began to emerge from the gnawing grip of addiction, his mind cleared and he wondered, what the hell am I doing here?  He asked his host when he could return to Canada. Ozzie insisted that he must first complete his training.  It was at this point that it dawned on Jack that he had no money, cellphone or means of transportation.  And, apparently his passport and ID had been confiscated.  The next morning Ozzie woke him at five o’clock, and said they were going on a 10 kilometer walk.  

     The route was along a country road, which ended at the trailhead leading to the Santa Cruz Mountains.  It was a rugged well-worn pathway with a gradual elevation gain.  Jack was panting as he tried to keep up with the easy pace set by Ozzie.  Even at this early hour, the temperature was around 26 degrees Celsius, and with the humidity it felt even warmer.  Soon he was sweating profusely, and the term ‘use it or lose it’ came to mind.  A few years earlier Jack had competed in Iron Man competitions, and now at 37 years of age he was hopelessly out of shape and was struggling on this relatively moderate trail.  Finally, Ozzie turned around and led the way back to the farm.  After a brief swim in the river, they changed clothes and went in for breakfast.  On the menu was Johnny cake, salted mackerel and mint tea.  Jack was just beginning to regain his appetite.

     The 10 kilometer hike became a part of their regular morning routine, and in the afternoons they did calisthenics and light weights in the yard.  Afterwards, they would swim in the river, mindful of watching for crocodiles.  As the days passed, Jack began to notice a marked improvement in his fitness level.  He was eating regularly now, and had started to put on some weight.  The desire for a drink was still strong, but he was able to supress the urge and continue to function without feeling that his stomach was tied in knots.  Soon the morning walk evolved into a slow jog.  And then each day it became a little faster.  By his fifth week at the farm, Jack had doubled the distance of the morning jog – now a run – and had exceeded Ozzie’s ability to keep pace.  Jack would now run 10 kilometers out along the trail, and then reconnect with Ozzie on the homeward leg.  His strength and endurance were increasing every day.

     After six weeks Ozzie told him one morning that they had an appointment the following day, with a dentist in Montego Bay.  Apparently Richard had spoken with a top dental surgeon who had agreed to install implants, and do any other cosmetic improvements necessary to give Jack a perfect smile.  They were booked for several nights in a villa at the Round Tree Hotel, where Richard would eventually join them to discuss the next phase of Jack’s training.  Ozzie had given Jack a little background about his older brother.  He shared that, “Richie is a big shooter in the mutual fund business and makes a ton of money!”  He had even paid off the mortgage on the farm, and regularly sends money to help their mother.  Ozzie continued, “He has a big job in mind for you, mon!”  Jack wondered, do I have any bloody say in the matter?


      Richard Meriwether was blown away when Jack opened the door at the Round Tree.  Ozzie had kept him abreast of Jack’s progress through WhatsApp, but hadn’t prepared him for the amazing transformation in the man’s appearance.  He had newly implanted white teeth, which contrasted nicely with the deep tan he had acquired during his stay at the farm.  More impressive though, was his overall look of fitness.  He had put on weight and no longer had the bloodshot eyes or frail appearance of a down on his luck homeless person.  Jack had even shaved off his beard.  This new improved Jack was a good looking dude, and Richard thought, I might actually have a chance of winning this thing with Tim Monahan.  He was even more convinced of it when Jack told him he was a McGill graduate and had previously worked for the Boeing Company.  It was hard to believe that the slobbering drunk he had met in Toronto, was once jet aircraft salesman.    

     Richard decided that the best way to win Jack’s support was to simply tell him the truth.  He explained about the competitive nature of the money business, and how he and Tim Monahan had made a ‘million dollar bet’ based on their disdain for one another’s approach to dealing with clients.  Richard said, “It was a crazy bet to make, on my part.  I was the one who was required to find a homeless person, and in six months get him trained and hired by a brokerage firm.  Jack responded sarcastically, “Like putting lipstick on a pig, and then pawning off the pig as an aspiring stockbroker … except in this case I’m the pig.”  Richard replied soothingly, “No mon.  You’re more like a George Bernard Shaw character in Pygmalion, and if you work with me on this I will reward you handsomely.”  Jack said angrily, “The hell with you, I won’t do it!”  Ozzie interjected, “Hush yo cryin, brudder!  You will do it certain, or we feed you to the croc-o-diles.   

     After much cajoling and further explanation, Richard finally convinced Jack that this was a sweetheart of a deal that might well set him on a new course in life.  He said that he would absorb all of the costs involved in preparing Jack for the challenge, and was also prepared to split the million dollar prize with him.  To seal the deal, Richard removed a Patek Philippe watch from his wrist and handed it to jack.  He said, “Jack, I want you to have this.  Let it be part of your new image as a high achiever.”  Jack thought, holy shit, this watch is worth more than a hundred grand!  Richard added, “And, don’t be fooled by my brother’s Patois colloquialisms.  It’s mostly a put on.  Ozzie is actually a VP at the bank of Jamaica, and has taken a leave of absence to help me out.”  Oz is a wizard at finance, and he can help you with all this stuff.  He handed Jack a satchel of books.

     When Jack and Ozzie returned to the farm they redoubled the intensity of Jack’s fitness program.  Also, two hours of each day were now set aside to study the materials Jack must master before writing exams for the securities business.  It wasn’t rocket science.  It was really just a question of memory work and gaining an understanding of the basic concepts.  Jack came to realize that any person of average intelligence could learn this stuff, and that success in the investment business was mostly about sales ability, rather than having academic credentials. Ozzie pointed out that talent was as cheap as table salt.  It was the ability to convince people to take action that put the ball in the net.  He said, “If you walk the walk, and talk the talk, you’re already half-way to accomplishing your goal.”  That goal was simply to get people to say, ‘yes.’  

     Two months later Jack flew back to Toronto and was greeted at arrivals by Richard Meriwether.  Richard drove him to an executive rental in the Beaches and told him the place was all his for the next six months.  It was a fully furnished condo, and below in the underground was BMW 7 Series sedan, for his use.  The refrigerator and pantry were stocked with food, and in the bedroom there were several suits in the walk-in, that had been tailored to Jack’s measurements.  Other clothing items and personal necessities were also provided, including silk pajamas, a robe and even Tom Ford, Tobacco Vanille cologne.  Absent of course, were any alcoholic beverages that might provide a temptation to the newly sober resident.  Jack assured Richard that his drinking was no longer a problem, that he had the addiction under control.

     Jack had easily passed the necessary exams and was now ready to apply to one of the investment firms.  First though, Richard wanted to create a bullet proof resume for Jack, and also help him to establish a ‘playbook’ for how he intended to generate sales in the rough and tumble brokerage business.  They decided that he would portray himself as a financially independent former Boeing salesman, who had experienced personal tragedy and taken some time off to revaluate his priorities.  He would offer as a personal reference Mr. Oswald Meriwether, a vice president at the Bank of Jamaica, who would attest to Jack’s character and confirm that he maintained deposits with the bank that were in the high seven figure range.  Jack was coached to say to prospective employers that he enjoyed working with people, and wanted to establish a new career helping them achieve financial success.


     Tim Monahan had called Richard repeatedly, ever curious as to how he was making out with the homeless candidate.  With just four weeks remaining in the six month challenge, he was feeling confident and reminded Richard that ‘a bet was a bet,’ and he expected to be paid promptly at the end.  Richard smiled into his cell phone and thought, I think I’ll pull this guy’s chain.  He then lamented, “The man is a train wreck and I’m not sure he’ll be ready.” He added begrudgingly, “But, don’t worry, I’ll pay you the million if I lose.”  Tim had asked him time and again, “Where are you hiding the guy?  Has he sobered up, written any exams?”  Richard had just responded with, “All shall be revealed in good time, mon.”  He urged Tim to be patient for the final four weeks as he attempted to get his candidate across the finish line.   As they ended the call, Tim felt a shiver of apprehension.  He thought, that slick bastard’s tone sounds off.  Somethings going on!     

     Jack got off the elevator at the 48th floor of First Canadian Place in downtown Toronto.  The receptionist asked him to take a seat while she announced his arrival.  A few minutes later a stunning blonde woman came into the foyer and called his name.  She looked vaguely familiar, and as he tried to place her, she extended her hand and said, “Hello Mr. Stedman I’m Gloria, Mr. Palmer’s executive assistant.  He’ll see you now, if you’ll please follow me.” They walked along a bustling hallway until coming to an area marked National Sales Office.  She led him to a glass fronted corner suite that wasn’t particularly pretentious, nor was the man who rose to shake his hand.  Terry Palmer smiled and immediately put Jack at ease, as he guided him to a small conference table.  He said, “Gloria, bring Mr. Stedman a cup of coffee and please hold my calls.

     Terry chuckled and said, “Jack, I love it that you decided to apply right at the top.”  He explained that he and his team monitored sales through 76 offices nationwide, that comprised over 1,600 advisors.  New applicants were usually screened at the local level, before final approval was granted by National Sales.  Jack responded, “I’ve been out of the job market for some time, and may be a little out of touch with hiring protocols.   In any case, your name was given to me by a former colleague at Boeing.”  He explained that Bob Murphy and he were former classmates at McGill, and they had both been recruited by the same head hunter right out of University.  Bob apparently remembered Terry from Montreal, back in the day.  Terry had noticed Jack’s gold signet ring with the ruby center stone.  It was another gift from Richard, and the impressive ring had McGill and MSc inscribed upon it.

     Jack talked briefly about his situation, and said that after much soul searching he had decided to change gears and build a career in financial services.  Terry cautioned him that it was a tough business, especially when you were starting from scratch.  He said that once each year they conducted a small rookie class, but most of their concentration now was on luring established producers from other firms.  Jack acknowledged that it might be a steep climb, but that he was perhaps an exception to the rule.  He had a proven sales record, and during his time at Boeing had established relationships with a large number of senior executives.  He said he wouldn’t require any financial support, as he had substantial personal resources at his disposal.  Terry was very impressed when Jack showed him his ‘playbook.’  It detailed a deep knowledge of alternative investments, complicated life insurance strategies and the benefits of a family office.  

     Terry said, “I want you to meet our president Brian Stoneman.  Let me make a call and see if he has a few minutes to spare.”  Jack went through the same song and dance with Stoneman, who was apparently impressed, because when he returned to Palmer’s office he was told that Gloria would take him into the boardroom to complete some paperwork.  In the meantime, Terry called Osgood Meriwether at the bank of Jamaica, who stated that he had knowledge of Jack’s good character and confirmed that he had substantial assets on deposit with the bank.  At the end of the day, Terry made him an offer of employment.  Jack was delighted, and discretely asked Gloria if she would like to celebrate with him over dinner at Sushi Masaki Saito.

     Gloria was quite tipsy by the time they checked into a room at the Four Seasons.  Jack had finally made the connection when she swung her shapely legs into the BMW.  It was the red shoes that triggered his memory.  She was the girl who had looked at him with disgust when he had been down and out on the streets.  He could still remember the staccato beat of her shoes as she had hurried past.  Jack slowly removed her clothing, but asked her to leave the high heeled shoes on.  It had been a long time since he had been with a woman, and he mounted her with vigor.  She moaned with pleasure and hooked the red shoes around his buttocks.  Later, as she slept, Jack got dressed and withdrew some money from his billfold.  He tossed it on the bedside table, before leaving the room.



     Tim Monahan was astonished when Richard called to tell him his candidate had been officially hired by a competitor firm, and that he was claiming the million dollar bet.  After a long pause Tim asked, “How is that even possible?  You told me the guy was a train wreck.”  Richard responded, “Well, we managed to pull him together and he got the job.”  He explained that Terry Palmer himself had hired Jack Stedman just a few days ago.  Tim said angrily, “This is bullshit, there’s no way that drunken bum could ever get a job in our industry!” He went on to suggest that it couldn’t be the same guy.  He accused Richard of using a substitute, a ringer. He said there was no way he was going to pay.  Richard explained to him that he had proof.  He had filmed and documented every step of the process.  He had even taken a selfie of the two of them, with Jack standing in the background on that first day.  Tim shouted, “I don’t believe any of this, and I’m not paying you a red cent!”  

     After Tim had blocked his calls, Richard went to confront him face to face at his office.  Tim refused to speak with him, and when Richard wouldn’t leave, the receptionist called security.  As far as Richard was concerned, his competitor was in breach of contract.  Except there was no written contract.  It was all verbal, and there weren’t any witnesses.  Richard didn’t need the money! That wasn’t the issue.  But, he had invested a lot of time and energy into the project, and had promised to split the prize with Jack.  Richard reluctantly called him to explain the situation.  He said, “I’m sorry, but there’s probably not going to be a big payday.” He also reminded Jack that when the temporary lease was up, he would have to vacate the condo and give up the BMW.  He was welcome to keep the jewelry and clothing, but otherwise he was on his own.   Richard concluded, “You’ll have to sink or swim in the new job.”

      The whole story about Tim’s bet with Richard had been known by a few friends in his inner circle.  They were also aware that Tim had reneged and was at serious odds with his competitor.  In the end, he was betrayed by one of his own colleagues who decided to leak the details to the Toronto Newspapers.  The press had a field day, building the story into a sensational exposé complete with the names and photographs of all concerned. They opined salaciously that anyone with a heartbeat could be trotted out as a financial advisor.  As outrage over this spread through the investment community, Tim and Richard were both suspended by their respective firms, pending an investigation by the Ontario Securities Commission.  Jack was called in to Terry Palmer’s office and promptly let go.  The firm simply wanted to distance itself from any negative publicity.  

~                        ~                        ~                   

      It was twelve noon when Jack strolled into the Library Bar at the Royal York Hotel.  He hesitated briefly when the barman asked, “What’s your pleasure, Sir?”  Finally he said, “Vodka on the rocks.”  Feeling critical eyes upon him, Jack turned on the bar stool and noted the impressive painting of George Locke, which hung over the mantelpiece.  The man seemed to be staring right into the depths of his soul.  Jack’s jaw quivered as the craving for a drink became undeniable.  He turned back to the barman and said, “Make it a double!”

By Michael Barlett


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