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Dayberry's gambling goes beyond poker

By Daniel Michaels, May 20th 2005
Tama, Ia. - Bob Derryberry bristles when he hears himself referred to as a "professional gambler."

Sure, he lists "poker player" as his profession on tax forms. He regularly plays in high-stakes games and even asked a judge last month to allow him to travel out of state to continue his livelihood - playing poker.

Even so, he says, he learned the game a long time ago and plays because he loves it.

"I never said I was a professional gambler," Derryberry says. "I'm 60 years old. I'm retired. I never did turn pro. I just always played."

As a hobby, poker appears to have been a lucrative one. When state and local authorities raided his home in January and seized his bank safe-deposit boxes, they found hundreds of thousands of dollars. That money came from poker, Derryberry says.

Not so, prosecutors charge. They say it was generated as part of a multimillion-dollar gambling ring run out of Derryberry's Norwalk home - one of the largest sports-bookmaking operations in the state. Now Derryberry faces felony gambling and money-laundering charges that could send him to prison for 45 years.

Derryberry won't discuss the current charges against him. He did, however, allow The Des Moines Register to watch him play poker, and he talked freely about his legal gambling.

"I am an aggressive poker player," he says, explaining the strategy he's used in thousands of games. "Playing defensively, protecting your chips, is not going to cut it."

High-stakes games keep him on the road

Before his arrest in April, Derryberry spent at least five days a week on the road, traveling from one casino to another.

He could be in Kansas City on a Monday afternoon, sitting in on a high-stakes game. On Tuesday, he'd hit Tunica, Miss., and then drive his black 2001 Pontiac Bonneville down to Louisiana. Come Friday, he'd swing north to casinos in St. Louis or back in Kansas City.

"I was doing that week in and week out. I was averaging $2,500 in winnings, probably more" a week, he says.

"I saw a $7,000 pot in Tama. I saw one kid bring in a $100,000 pot in Tunica. After a week, you may pick up $10,000 to $12,000. It's hard to do, but it happens. The biggest win I've had in one game is $8,000, but I've won $5,000 a lot of times."

Derryberry says he's been on the other side of luck, too.

"I went to Kansas City and lost $6,000 in one night," he says. "I just turned around and went home."

Sometimes success is a matter of perspective.

"Another time in Kansas City I had $7,500 on the table, but things were going bad. . . . In the middle of the afternoon I started getting some of my money back. Then I got even. Toward the end I had won about $800, and I sailed out of there. I felt like I won a million bucks."

Louisiana is his favorite place to play. "In New Orleans and Shreveport, there are a lot of bad players with a lot of money," he says. "I went down to Shreveport once, and I was sitting at a table where I haven't seen these guys before. They were from England, Ireland and Holland. They just kept plugging those pots with money."

In high-stakes poker, money is a tool as well as a goal. Sometimes big money is wagered on pure bluff. "Some guys with money try to buy a pot," Derryberry says. "You do that too much or at the wrong time, you can dig yourself in deep."

Derryberry's out-of-state forays are over for now, thanks to the $58,500 bond he paid to be released on the gambling charges and the authorities who seized nearly a half-million dollars of cash. He requested permission to travel across state lines to play cards while awaiting trial, and 5th District Judge Gary Kimes agreed - if Derryberry paid an additional $35,000 bond.

"I'm not going," Derryberry says now. "I can't afford that extra bond. Plus it costs in travel expenses and hotel rooms to go out of state."

Instead, he makes one-day runs to Iowa casinos. His favorite in-state destination, until it temporarily closed because of a tribal dispute, was the Meskwaki casino near Tama. It hosted some of the highest-stakes games in the state on Fridays.

On a typical trip there last month, Derryberry is dressed comfortably - slacks, button-down long-sleeve shirt and brown loafers. He will sit for long stretches at the table, he knows, because he routinely plays for 12 hours at a time. His longest stint at a table was 42 hours.

Arriving at midafternoon, he heads straight for the poker room. Other activities at casinos hold little interest for him. "You should stick with what you are good at. You have to stay away from the craps tables and the blackjack tables," he says. "If I've seen it once I've seen it a thousand times where a guy will make a good score at the poker table then hit the main casino floor. In a couple of hours, they are nearly broke and trying to make some money back at the poker table.

"It's a funny thing. I can bet $1,500 on the flip of a card without blinking. But when I put $100 or $200 in a slot machine, I get damned mad at myself. When I dump money down those slots, I feel like I just should have taken that money and thrown it out into the street."

'My paycheck was always a little light'

Derryberry learned to play poker in Korea.

He joined the service when he was 18. His life until then had hardly been flush. Born in Memphis, Tenn., Derryberry moved with his single mother and three siblings to Arkansas while he was still young.

His mother left for California when he was 12 to be with a boyfriend. That relationship lasted a couple of years, Derryberry says, and he lived with an uncle stationed in the Panama Canal Zone in the meantime.

"After that, it was Oklahoma, Arkansas, then back to Oklahoma again," he says. The family often lived with relatives. "There was not a lot of money around in the "50s," he explains.

He had graduated from high school and was working on a freight dock for $1.50 an hour when he decided to enlist in 1961. He became an infantryman and was sent to Korea. By that time the war had ended, but the border situation was tense.

Derryberry and his fellow soldiers whiled away their off-duty hours by playing poker.

"They taught me to play over there," he says. "We played payday stakes. You played on credit until payday. . . . My paycheck was always a little light."

The Army transferred Derryberry to Germany for his final 18 months of enlistment, and he was assigned as a cashier to an accounting department at the base in Nuremberg. While in Europe, he was injured in a traffic accident, hitting his head on the windshield when the driver lost control and the car hit a building.

For a month, Derryberry recuperated, and he spent a lot of that time playing cards with off-duty buddies and other patients.

"We played cards and drank beer," he says. "We snuck the beer in. One of the guys made friends with a beer-truck driver. We would lower a rope from the fourth-floor window, he would tie a case of beer to it and we would pull it up."

He left the service in 1964 and went to college for a year in Oklahoma before moving to Iowa the next year and attending one semester at the American Institute of Business in Des Moines. Derryberry later joined an apprentice ironworkers program and worked in the profession for about a decade. He married, divorced, married again, divorced again. Raised two daughters and a stepdaughter.

After he quit being a construction worker, Derryberry sold insurance and siding. All the while, he played poker. And, authorities charge, he gambled illegally.

His first Iowa arrest for illegal gambling was in May 1967 and led to a $15 fine. Derryberry says he, some co-workers and neighbors were just playing cards. "It was 10-cent and 25-cent poker. We were sitting in a neighbor's house up on 14th Place, drinking beer. About 3 a.m., the police kicked in the door and hauled us off to jail. I was the only guy who had 15 bucks to bail myself out. . . . One of the cops said, "You must be the big winner." I was," he remembers, still grinning.

In 1986, Derryberry pleaded guilty of running a bookmaking operation from the house in southeast Des Moines where he lived then. He spent 20 months in prison for shooting a man in 1988. In 1996, he was arrested at his Norwalk home and apparently received a deferred judgment, although all record of the conviction has been erased by the court.

By August 1997, things were looking up for Derryberry. "I played poker all summer," he says. "I didn't win a fortune, but I never had to go back to work. I can live pretty modestly. I only have to take care of myself."

It's a friendly game, but no "small stuff'

When Derryberry walks into the poker room at the Meskwaki casino, players already surround four of the eight large tables.

Poker is played in a separate room just off the main casino floor. Inside, each oblong table is circled by chairs for 10 players and a dealer. The tabletops are green, but the material isn't the soft felt that one might expect. Instead, it's heavy vinyl decorated with embossed diamonds, hearts, clubs and spades.

Derryberry asks the counterman, who runs the room, which players might be expected for "pot night" - when the maximum bet allowed is the amount of money in the pot. In pot games, the stakes rise quickly: One player can bet $400 if that's how much is already in the pot. The next player can raise $800, the next $1,600. The third and final raise could be $3,200.

"There are no pot games scheduled tonight," the counterman tells Derryberry.

"What do you mean?" Derryberry replies. He's annoyed. "There's pot poker night every Friday."

It's really every other Friday, he's told. Derryberry resigns himself to play for lower stakes, at least for a while, until other pot-poker players arrive and they can arrange a game among themselves. "I only play up here on Fridays," he says later. "I don't worry about the small stuff."

The small stuff for him consists of maximum bets and raises that range from $20 to $40. In pot games, "there is a $300 minimum buy-in," he explains. "Most guys start out with $500 or $1,000. But I've seen $50,000 on the table. Some big guys have been coming down from Minnesota."

Casinos make money from poker games by charging a fee, ranging from a few dollars each hand to a percentage of each pot. In return, they provide a dealer for each table and the counterman, who converts cash to chips, keeps tab of openings at the tables and manages the waiting list.

Derryberry draws $500 worth of green-and-red $5 chips and white $1 chips. He finds a seat in a far corner table.

By 6 p.m., six tables are full. Nearly all the players are men. A casino employee pushes in a dinner cart, which serves free ham-and-potato casserole.

Derryberry moves to another table, and the men there agree to a modified pot game - if the nonpot players at the table drop out of a hand, the others can go over the $40 maximum.

The men at Derryberry's table are older. They have gray or graying hair, or are balding. The youngest looks to be in his mid-30s, the oldest in their 70s. Some wear hats, usually baseball caps. All are dressed casually, most in blue jeans and T-shirts.

Some are silent, almost glum.

The most intense is the youngest player. He sits on the edge of his seat, leaning over the black vinyl armrest around the table. He wears an almost constant scowl as he glares at each card the dealer flips. He's silent except to announce his bets and rarely calls his hand, flipping the cards face up on the table if they're winners, face down if losers. The young man holds his own for several hours, although his stack of chips dwindles to about half its original size. Around 10 p.m., he stands up and leaves. Another player takes his seat.

All the tables are full now.

Derryberry knows the people he plays cards with in Iowa and Missouri. "I've played with most of them for years," he says.

Many are businessmen, people who inherited money, or retired farmers who sold off their land, Derryberry says. "There is a guy who comes here - I am not going to tell you who he is - who is worth about $20 or $25 million."

He won't identify any of the players other than by first name or nickname. "It's their business who they are. A lot of them don't want their wives to know how much they are gambling," he says with a chuckle.

Being acquainted with your opponents can be an advantage, Derryberry says. "Everybody has his little quirks. One guy, if he hits the card, he moves his left hand back towards his chips. Not a lot. Just a little. But his hand moves back toward his chips. Another guy, when he is bluffing, he will always ask questions like, "How have you been?" or "How are you doing?" When he's got something, he doesn't say anything.

"Those quirks are called "tells." It's a giveaway. It's a flaw in your game. To play poker, you have to have control of your emotions."

Pistol shot puts friend of wife in wheelchair

Norman Nance knows that Derryberry doesn't always control his emotions.

Nance had been dating Diane M. Derryberry, Bob Derryberry's estranged wife, in 1988. The Derryberrys had been married six years and were on the verge of divorce - if Bob would just sign the papers. He refused.

On Oct. 28, Nance and Diane Derryberry met at the Cabaret Lounge in Clive, then left for dinner and a Dowling High School football game. He drove her back to the bar about 10 p.m. so she could pick up her car.

As they sat in his white pickup truck talking, they saw Bob Derryberry's car pull into the Red Lobster parking lot next door, Nance recalls.

Derryberry got out of his car carrying a Browning 9 mm semiautomatic pistol and walked toward the pickup. Diane Derryberry got out and tried to calm him down. Police reports say Bob grabbed Diane by the neck, held her against the truck and pointed the gun at her head.

Nance says he was sitting in the truck with the doors locked and windows closed when Derryberry aimed the gun at him and pulled the trigger. Derryberry says that he was upset, but that he only wanted to scare his estranged wife and Nance. He banged the gun on the truck, he says, which caused the pistol to go off accidentally.

A bullet smashed through the passenger-side window and hit Nance in the shoulder. It tore through his body and severed the spinal cord just below the last cervical vertebrae.

Nance spent more than six months in the hospital. He's been in a wheelchair the past 14 years. He'll never use his legs again.

Derryberry was originally charged with attempted murder but was allowed to plead guilty to a lesser charge of going armed with intent. Sentenced to five years in prison, he was paroled after 20 months.

"He got off with a slap on the hand," says Nance, who still lives in Warren County and now keeps a gun close at hand. "I got a life sentence.

"This man is very intelligent, but he has no common sense," Nance says. "When he gets to drinking, he kind of goes off on a wild side."

After the shooting, a psychotherapist's assessment was included in the evidence. T. Nicholas Tormey said Derryberry had been suffering from depression and needed treatment for an alcohol problem.

"That wasn't the real story," Derryberry says now. "We were a family in crisis. That's what it was."

He says he still drinks occasionally, "but I don't drink much at all. There is no liquor in this house."

Diane Derryberry did not comment for this article, but her contentious relationship with Bob Derryberry has been mended. "Diane went to Shreveport with me this winter," Derryberry says. "I get along with her better now than when we were married.

"When we were married, most of our problems were over money. We were always arguing about money."

Money is still part of their relationship, authorities believe. The Warren County attorney has accused Diane Derryberry in court papers of rushing to Evening Shade, Ark., soon after police raided her ex-husband's home in January. Once there, authorities claim, she emptied a bank safe-deposit box just hours before Arkansas state troopers arrived to seize the contents for Iowa investigators.

Diane Derryberry's attorney, Keith Rigg, says the timing of the bank visit was a coincidence.

'Country poker' yields a nice return

Derryberry, stocky and sociable with friendly blue eyes, chats up the counterman at the Meskwaki poker room as well as the dealers who rotate from table to table. Everyone seems to know him, including the women who serve complimentary coffee and soft drinks from push carts.

"They all know me because I tip for whatever I get," he explains. "I give them a half a buck or a buck" for the free drinks. If he wins a pot, he regularly flips several chips to the dealers.

"They are tough jobs that don't pay much," he says. "In these places, the big guys make the big money. (Casino staff members) don't. They work for tips."

Derryberry is alert but relaxed while he plays, occasionally sipping from a bottle of water or popping a breath mint to hold down his cigarette craving, because smoking isn't allowed in the poker room.

Every hour or two, Derryberry walks out onto the main casino floor to smoke a Dunhill and stretch his legs, almost always greeting somebody he knows or chatting with the beverage cart servers.

He says he doesn't worry about leaving his stack of chips unattended during his smoke breaks. "This is country poker," he says. "We all know each other. We trust each other. If somebody has a run of bad luck, we will lend each other money."

About 3 a.m., Derryberry stacks his chips in plastic trays, pushes away from the table and walks up to the counter to cash in - $3,300.

"That puts me $2,800 ahead," he says.

Not bad for "country poker" and much better than his take the previous Friday at Meskwaki, when he cleared $670.

"That's still more than $50 an hour," he says, "which is a lot more than most jobs pay."

Stress from raid, criminal charges builds

Since the raid on his house in January, Derryberry has twice undergone heart surgery, says his attorney, F. Montgomery Brown. "He tried to quit smoking but can't. The stress is too much for him."

Authorities have charged Derryberry with ongoing criminal conduct, illegal gambling and money laundering. They've asked the courts to take his home from him and seized hundreds of thousands of dollars. And they aim to put him away for what could be the rest of his life.

"I really try not to think about that too much," Derryberry says. "There's really nothing I can do about it anyway."

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