By Nadia Oehlsen

Before leaving the parking lot, the man seated next to me has determined that I’ll bring him good luck. We’re in a plush, air-conditioned bus destined for the Empress Casino in Hammond, Indiana.

The couple behind us laughs and converses with the man in Tagalog. Their chatter mingles with at least two other languages, a movie on the small TV above our heads, and a synthesized version of “Besame Mucho” on the dashboard radio. The driver warns us not to lose the paper passes he’s handing out. Anyone who can’t return the pass later tonight will have to pay $10 to get home.

I’m one of 17 passengers waiting for this evening’s 7 PM Tuesday departure from 5008 N. Broadway; six people look younger than 50, four are white.

“Free Trips and Buffet to Casino” promises the sign outside the office of Chicago Entertainment Tour. A fleet of white buses and vans, with the company name and phone numbers painted on their sides, beckons enough passengers to support four to six trips each day from Uptown. The earliest departure is Saturday at 8:30 AM. The latest, by reservation, departs any night at 8:30.

“Is this your first trip?” the man next to me asks as our bus pulls onto Lake Shore Drive. When I say its my third in the past month, he frowns. “You shouldn’t go too much. You’re still young. This is for old men.”

He’s in his mid-60s and takes the bus up to three times a week, often with the friends seated behind us. He says he loses more money than he wins. When he won $400 recently, he and his wife gambled it away the next day. “It keeps me young,” he says.

Since his wife didn’t come out tonight he’ll have to rely on me to bring him fortune. I tell him I’m not lucky–the first day I lost $30, the second I lost $20, won $60, then lost $70. Like me, most of the people on the bus stick to slot machines, though a few favor the blackjack tables, where the stakes are higher but the odds are supposedly better.

As we pass McCormick Place, the man informs me that he has four adult children living here and one in the Philippines. I tell him about another gentleman I’d met on a bus returning from a Saturday afternoon trip. That man was in his mid-70s. He’d smiled sheepishly as he tallied the results of his most recent outings. “Today I lost $150,” he said. “Yesterday I won $80. The day before I lost $70. You win and you lose. I lose a lot more than I win.” He said he moved here from China 50 years ago, raised a family, then moved with his wife to South Carolina some 20 years ago. They came back in 1992, moving into the house they still owned near Foster and Clark to be close to their children. “My wife died last year,” he said. “After that, I started going here.”

He’d taken the free bus to the Empress almost every day for the past six months. The 10:30 to 4:30 trip was his favorite, he said, because he’d struck up friendships with other people who favored that trip and the free buffet provided a good lunch. He marveled at the business savvy of whoever founded Chicago Entertainment Tour, which he reasoned must make good money. According to the Indiana Gaming Commission, Empress’s Hammond casino took in $196 million last year. He figured that meant it grossed about $80 per person per day. Minus the cost of employees and free food and paying bus companies like this one, he mused, the Empress would take about $40 per gambler. We guessed the bus company might make at least a quarter of that per head, because we’d have to pay $10 if we lost our passes.

Chicago Entertainment Tour was started last year by Quynh Nguyen. The company picks up passengers from a couple other north-side sites besides the lot at Argyle and Broadway. Each destination is painted near the doors of the buses, making it easy to spot as they queue up next to those of other companies in the Empress’s parking garage. Nguyen says only that his company is small and that he took on debt to acquire his vehicles.

I look out the window as our bus cruises up the Skyway, past the bungalows, auto repair shops, corner stores, and neighborhood taverns of the southeast side. The man next to me has turned somber. “There are a lot of broken homes from gambling,” he says. We cruise past the scrap piles, foundries, chemical plants, and factories of northwest Indiana, then pull past the Hammond water-treatment plant to the glowing Empress Casino in the Hammond Marina. My neighbor’s spirits are back up. “You’re going to bring me luck,” he says happily once again.

As we step off the bus, a casino employee hands each of us a chit for a free buffet coupon. We walk through sliding glass doors, past the valet service and free coat check, and go up an escalator. Most of the group ignores the colorfully lit waterfalls and fake plants gracing our ascent, though a few look around appreciatively, pausing to contemplate the iron statue of Neptune rising from a fountain at the top of the escalator. A muscled man with a flowing beard, Neptune wears a crown and a seaweed loincloth; in one hand he holds a pitchfork, in the other the reins of a chariot pulled by winged horses poised to fly out of the pool at the edge of a waterfall.

We line up at the check-in desk to present our vouchers, picture IDs, and Empress Club cards. The information is entered into a computer, and then we’re handed meal tickets, key chains, and Empress Fun Books full of coupons for free muffins, free nachos, and deep discounts on T-shirts, fanny packs, and water bottles.

The dining room looks like a giant fish tank, with outcroppings of pink, yellow, and green coral and huge windows offering a fine view of Lake Michigan. I’m the last to make my way through the buffet, which is laid out in what appears to be the broken hull of a sunken ship. The three Filipino friends smile and wave for me to join them at their table. In 15 minutes we down a feast of prime roast, ham, egg rolls, soup, fried chicken, pizza, salad, steamed vegetables, fried rice, rolls, pudding, cobbler, ice cream, pop, and coffee. Another woman from our bus and her mother sit with us, but they take their time eating. They plan to skip the 8:30 cruise, which leaves in five minutes. They’ll graze the dining room, maybe take a stroll along the lakefront, then catch the 10:30 cruise to gamble for 45 minutes before they’ll catch the bus home at 11:30. I’m told the boat rarely leaves the dock, though we can only board at specific departure times. Once we’re on board, we can leave after 15 minutes or stay on the rest of the evening.

Inside, the Empress looks like most other gambling boats moored on America’s lakes, rivers, ponds, and irrigation ditches: rows of slot machines abut green tables for craps, roulette, and card games. My friends drift off toward the slots while I stand frozen, listening to the din of hundreds of machines playing the same three notes at different times. Every few seconds they congratulate small and large victories with the universally familiar chords for “Ta-Da!” I start to wander the different levels of the boat–Diamond, Emerald, Ruby–looking for a few slot machines that Boris claimed are unusually generous.

I’d met Boris, a lucky or deceptive Ukrainian immigrant, on my last visit here. I look for him as I pass a blackjack table, though I don’t expect to see him because he prefers to catch the 1 to 6:15 tour. “One o’clock is best,” he told me. “You come, eat a nice lunch, then come on the boat at two o’clock. The dealers are tired then, so you can win more.” On the day we talked, I’d won then lost. I only allow myself to lose $30 per visit, so I decided to cut my losses and kill time watching more sophisticated gamblers. Then I recognized Boris from our bus. The brawny 50-something man was hunched over his cards at a blackjack table, wearing a khaki shirt and trousers and heavy gold jewelry.

He lost several rounds, won a few, and tipped the dealer as he pushed away from the table. “Today is not a good day,” he said. “I lose $250 and I stop.” He claimed he’d won $1,500 at blackjack the day before and had netted some $20,000 in the two months he’d been riding Chicago Entertainment Tour’s buses to the Empress almost daily.

With two hours until our bus left, we sat at two out-of-order poker machines, and Boris launched into his life story. He came to the U.S. from the Ukraine in 1978. In 1992, he said, he was working as a taxi driver in Los Angeles when six prostitutes jumped into his car and begged him to drive away quickly. After they’d escaped their pursuers, the prostitutes decided to celebrate by taking a $300 round-trip cab ride to Las Vegas. “It took me two-and-a-half hours,” Boris recalled. “I drove like crazy. I thought I would see a show when I got there, but I started gambling.”

Boris began to go to Vegas regularly. Whenever he came out ahead, he’d buy a money order made out to himself and mail it to his apartment in LA. That way he wouldn’t gamble with his gains. “You have to bet $200, $300 to make money, but you don’t bet it all at once,” he said. “I saw a guy here put $700 on one bet. He turned pale. He was shaking. I said, ‘Hey, I think you’re getting out of control. It’s better to lose one little finger than lose a whole arm.’ He said, ‘Mind your own business.’ He won, but it’s not worth it. Maybe his heart would stop.”

Boris said he never plays with a female blackjack dealer, or a black one. When I asked why, he shrugged and said, “I just learn over time.” He explained that for him women are just “for the night.”

He said Trump used to provide free bus rides to its Gary casino from Uptown, but those stopped in February. Boris speculated that too many homeless people were taking the free ride to eat rather than gamble. He thought that was why Chicago Entertainment Tour required passengers to carry at least $50 cash. Some regulars come to the Empress just to eat, he said, but most gamble at least a little on every trip.

Between taxi-driving stints, Boris was a tool-and-die maker until two years ago, when he hurt his back and started collecting social security. Now gambling was his business, and if he’d really won $20,000 in two months it was treating him well. He said he was afraid Empress would somehow discover his winning streak and find a way to stop it. He never inserts his Empress card into slot machines, and if dealers ask him if he wants to use his club card to gain points toward prizes and discounts he says he doesn’t have one.

“Come, I show you which machines to play,” Boris said. As we picked our way through the crowd, he bemoaned the fact that few people ever pull the now-superfluous arms on slot machines, preferring to set the games automatically by pushing buttons that say “Spin” or “Bet Three Credits.” He said he always pulls the arm at least once; only then will he settle for button pushing the rest of the session. “You play the slot machine like a woman,” he explained. “You do it once hard, then after that you do it gentle.”

Boris, who now lives with his third wife, also scoffed at how people choose their lucky machines. “People think the new machines are better,” he said. “That is the opposite. If the new machine costs $10,000, it won’t pay out much until it’s recovered $10,000.” Finally, Boris led me to a “Lucky 7s” dollar slot machine on the Diamond Level. “This one I won 500 coins,” he said. Then he led me to another one on the Emerald Level. “This one I won 300 coins,” he said. “You put 30 coins in and then you win.”

I try to find these machines on my next visit, yet I’m confused. I know they were both in back corners, but tonight every back corner and every machine looks the same. In a corner of the Emerald Level, I meet a young blond man from our bus. He’s consoling a stunned African-American woman in the general vicinity of where one of my lucky machines should be.

“She just got red, white, and blue 7s, but she only put in one token. If she’d put in three tokens, she would have won $10,000, but she only put in one, so she got nothing,” he tells me. Then he turns to the woman and says, “They woulda come and given you a big check and taken your picture to put in their magazine. Your girlfriend woulda been standing behind you going, ‘Hey, wassup?'” He shifts two large plastic cups filled with tokens from one hip pocket of his overalls to the other. He’d just won $450.

“Don’t lose it,” I say.

“I won’t,” he replies with confidence.

Sure that my lucky machines have been tapped by others, I take my time losing my $30. I buy an ice cream cone for 25 cents with a coupon from my Empress Fun Book. Then at 11:20 I get on a Chicago Entertainment Tour bus destined for Uptown. The woman and her mother who waited for the 10:30 cruise are here, as is the blond guy, who admits he lost $200 of his winnings right after he talked to me. The Filipino man who was sure I’d bring him luck must be on another bus. I don’t know if my charms worked.

Art accompanying story in printed newspaper (not available in this archive): photos by Jim Alexander Newberry.