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EDA Director Jennifer McDonald parlays casino winnings into real estate investments

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Jennifer McDonald displays envelopes of tax receipts from Charles Town’s Hollywood Casino winnings. Photo/Roger Bianchini

FRONT ROYAL – “Do you want my Charles Town winning story or is that too light – should I give it to a competitor?”  Front Royal-Warren County Economic Development Director Jennifer McDonald asked in a late January text.

“Give nothing to ‘no one’ other than your old pals at Royal Examiner,” came this reporter’s stern reply.  How light of a story, was the follow up question as the competitive juices settled a bit.

“Somebody saw me win big at Charles Town on Sunday (Jan. 14) and is now telling everyone,” McDonald replied, expressing a desire to see the story told accurately.  “What, you don’t trust social media and word of mouth to accomplish that?” I wondered.  “What did you do, hit a Trifecta on the ponies,” I asked.  No, rather it was an $18,000 slots jackpot at Charles Town’s Hollywood Casino.

“WOW, how many days and dollars were you up there pulling those one-armed bandits before THAT happened,” I asked by phone a short time later.  The answer, delivered the following day at her office with some support documentation, was not what was expected.

With questions having arisen in the past year about real estate investments she made in recent years under the banner of her personal real estate company “Da Boyz” (named for her favorite NFL team, which she said I could note WITHOUT my descriptive team adjective), McDonald thought this series of events offered an opportunity to clear the air, not only about her Sunday, January 14 winning trip to Charles Town and Hollywood Casino, but what she explained were about three or four years worth of comparable visits.

Do what – comparable how?!?

McDonald explained that she used to spend a little money playing the penny slots, taking home an occasional payout of $300 or so now and then – enough to keep you interested.  She credits her sister with development of a strategy that when a penny slot win would come in, to take $100 or $200 of that up to the next level slot, the dollar machines.

“I did that and started to win $1200 to $1500 and then she said, ‘Take $100 or $200 of that to the next level; and on her advice I kept doing that and it just has worked for me,” McDonald said.  We asked if the “system” worked for her sister as well as it has for her – “No,” McDonald replied with a sympathetic laugh.

She said winning hits on a dollar machine can come in around $1,200 to $2,500, and the $5 machine payoffs can come in anywhere between $3,000 to $15,000 – and of course there is the potential for one of the specialty jackpots hovering around $18,000 to $75,000.

Okay I reasoned, that is the theory that keeps people returning to casinos the world over – that BIG payday just over the horizon – but you know what they say about “a sucker born every minute” and “the house always wins in the end”.

McDonald explained that she will utilize “free slot play” or house money that regular customers may receive as an incentive, and “no more than $200 of my own money, and if I don’t hit anything with my free-slot play or my $200, I leave.  About the last four years I have been extremely lucky with this system I have right now,” McDonald said.

How lucky, we asked.

McDonald slipped a sheet of paper across her desk with a series of typed dates and numbers.  Scanning the sheet, I realized that the 22 lines taking up about half a page reflected only four days, November 22 and 26, and December 3 and 10; the payout amounts ranged from $1,500 to one of those apparent jackpots of $36,000.  The most hits in one day were 12 on December 10 – the first five on that date ranged from $1,270 to $3,000, followed by $8,000 and that $36,000 jackpot, followed by five more payouts between $2,000 and $6,000, totaling around $71,000.  Some late calculating indicated the total on the page for the four days shown was just over $102,000.

There was also a total at the bottom – “These numbers obviously don’t total THAT number,” I observed.  “Look under that page,” she suggested.  Six more full pages of dates and payouts were listed.

“THOSE add up to THAT number,” I guessed of the final page total of over $800,000, a number she explained reflected her winnings from her visits to Hollywood Casino in 2017.  And if not as good, her totals from the previous two years were also significant, both totaling over $500,000, she said.

“I have taken the money that I’ve won and I have paid for the educations of my stepdaughter, two of my nieces and my stepson.  I bought myself a truck; and the remaining I decided last year that I was going to start investing the money, rather than just letting it sit.  So, I started to acquire investment properties … and I’ve been able to make significant deposits on them,” she said of her real estate investments under Da Boyz banner – at least somebody using that nickname is good at something, I suggested, drawing a scowl.

As she has explained before to Royal Examiner, in her position as the EDA executive director, McDonald is forbidden from investing in commercial real estate.  However, with her background in real estate, she may invest in residential property.

My goal for this year is to win enough money to invest in some additional properties,” she added.  In addition to that January 14, jackpot hit for $18,000, she produced photos on her phone of hits of $6,000 and $24,000 on January 2, pointing out there were others she had not photographed.

Happy New Year, indeed!!!

Okay, while not a gambler by nature even your humble reporter can see that something beyond luck is at play here – I pressed her for a hint at the “system” she must not be sharing – “There’s got to be more to it; can you whisper it in my ear? Just between us. – You can trust me, I’m a reporter,” I reminded her.

But other than a favorite “quick hit” dollar machine, McDonald said there wasn’t a system other, apparently, than Lady Luck.  Speaking of luck, she said she did hit one $75,000 jackpot on that favorite “Quick Hit” dollar machine – I guess it is her favorite!!!

JACKPOT!! – McDonald said her favorite ‘Quick Hit’ dollar slot once paid off to the tune of a $75,000.

Looking at these winning-date visits averaging three to maybe six a month at Charles Town, we suggested some teetotalers might suggest she has a silly, little gambling problem.  Of course, I think a wise man once said “it is only a problem if you are losing,” not if you’re threatening to break the casino bank.  McDonald estimated that she may leave empty handed about a third of her visits, usually being able to net at least several hundred dollars in winnings.  She said her visits are dictated by work and personal schedules.  As for leisure time, when you’re hot, why not? – And if you’re not, go home early.

With such a disciplined approach, we asked how much she had to spend to reach the level of winnings she was describing for the past several years.  She produced another tax reference with a worried look – no wonder, it read $666.

“Well, THAT explains a LOT!!!” I offered.

“You have assistance from the dark side – at least you’re not averaging $666 in annual expenditures, are you,” I asked edging my chair closer to the door.  She explained that amount was an adjustment to her taxes to cover her own money spent above what the casino had deducted when it took taxes out upon payment of winnings.

After a little research she estimated averaging about $1,000 of her own money per year to achieve her winnings.  Recalling her system of moving up the slot ladder with lower-tier winnings, we asked if she thought she might actually be spending more house money than her own to realize her winnings.

“I most definitely have. They sometimes have drawings over there and I have won additional free slot play through those – anywhere from $250 to $1000 free slot play in addition to my weekly free slot play.  I love winning on their money,” she concluded with a smile.

Other than developing a “system” where she may be utilizing more house money than what she brought with her, what draws her to Charles Town’s Hollywood Casino, we asked.

“I have tried other casinos and I have not found a place that has a staff that is as polite, and helpful as Charles Town.  I feel safe when I go over there; they know you by first name – I just love going there because of the atmosphere,” she said.

HEY, what’s not to love about an atmosphere of personal dominance, where in the end only the house is supposed to dominate?  Our guess is she may love going there more than they love seeing her coming these days – or not.

Chances are the unlucky on any given night at Hollywood Casino outnumber the lucky – and hearing this story, that number is likely to go up – THAT ought to be worth a few more “free slot” plays, think …

1 Comment

1 Comment

  1. Ed Dumire

    February 12, 2018 at 6:07 am

    Happy that someone local is winning and commend her for the generousty she has shown to her family and the investments made in the town.

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