In the D.C. region, conversations often start with, “What do you do?” WTOP’s “Working Capital” series profiles the people whose jobs make the D.C. region run.
Before Maryland had casinos, the only place to roll dice, play slots or bet the farm in the D.C. area was Hollywood Casino at Charles Town Races, which is why all these years later, most of their players are driving in from Northern Virginia and Maryland.
The song from the Broadway musical Guys and Dolls made famous by Frank Sinatra, titled “Luck be the Lady,” has been associated with casinos for decades, but some guests at Hollywood Casino may believe their good luck charm is a man; his name is Brent Grubb.
Over the last 15 years, the native of Inwood, West Virginia, who deals blackjack, roulette and novelty games — including three card poker, four card poker and Texas Hold ’em — has witnessed players win incredible amounts of money.
“Players will bet $25,000, $35,000 a hand, which will turn into $100,000 when they do splits and doubles,” Grubb said. “We’ve had people win like $2 million.”
Can you imagine your reaction to winning that amount of money? If you’re thinking the players scream and jump up and down, you’d be wrong.
Grubb mostly deals for high limits players.
“They don’t show a lot of emotion, win or lose,” he said. “It’s almost like a job to them.”
Some dealers do get nervous when they start dealing high limit blackjack, fearing they will get in trouble if someone wins big, but they don’t. After a while, Grubb said you don’t look at it as money, it’s just chips.
Roulette players, on the other hand, are not as subdued. Grubb said the most he’s witnessed someone win at the wheel is $60,000.
“They’re a little more emotional,” Grubb said.
During his life, Grubb said he’s only had two jobs. Before he picked up decks of cards and chips, he spent 16 years in sales.
“The job I did before, I loved, but then the economy went bad, blah, blah, blah, and I got burned out with the sales job,” he said.
A former boss introduced Grubb to the world of gambling during trips to Las Vegas and Atlantic City. He said he noticed they were always playing with the dealers who were fun.
“We might have not won every time, but they were nice,” he said.
Just as Grubb was looking for the next chapter in his professional life, he read that his hometown casino would soon have table games.
Grubb reached out to Charles Town Races thinking this was the perfect time to try his hand at being a table games dealer.
“I was planning on being here two or three years, and now I’m here 15 years later,” he said.
The training took two months after a two-week introduction, and he said he constantly had a deck of cards in his hands so he could practice shuffling.
When it was time for Grubb to make his debut on the casino floor, he admitted he was nervous, which he said is normal in the beginning.
“Everybody was. We still talk about it to this day,” Grubb said. “When you are asleep, you will dream about cards.”
He said a good table games dealer is a performer and the casino floor is their stage.
“They shouldn’t act like robots. It’s important to get to know the guests and make them feel comfortable. They will treat you a whole lot better that way too,” Grubb said. “We have regulars. They get to know you, they ask about your kids.”
Over the last 15 years, Grubb said an important lesson he has learned was the guests not only look for dealers that they’ve won with in the past, but they want to play with dealers they like.
“The players will come in and they will lose but literally say, ‘Hey I lost but had a good time, thanks,’” Grubb said.
When it comes to rookie players, Grubb said they should listen to the dealers, because they do give advice and they want you to be a winner.
“That’s how we make our livelihood, is by them winning and tipping us,” Grubb said. “So yeah, I’m rooting for them.”
When it comes to tips, they are pooled and split between the dealers who’ve worked over a 24-hour period.
“I’ve had nights where I’ve dropped $80,000 in the toke box,” Grubb said. “So that’s tips. That’s not every day, but I’ve had that.”
He said he loves his job at Hollywood Casino and said the advancement opportunities with the company make it a perfect place for young people to get into the business. He said if he could have, he would have started earlier.
Get breaking news and daily headlines delivered to your email inbox by signing up here.
© 2025 WTOP. All Rights Reserved. This website is not intended for users located within the European Economic Area.
