Alex Nussbaum and David Voreacos

Bloomberg News

Even in the underbelly of North Dakota’s Bakken oilfields, the murder of Doug Carlile stands out, a tale of a Matt Damon look-alike felon, an Indian tribal leader and an accused hit man with a check list that included items like “practice with pistol.”

There’s even a voice from the grave: “If I disappear or wake up with bullets in my back, promise me you will let everyone know that James Henrikson did it.”

Those were the words Doug Carlile spoke to his family about his business partner before a masked gunman cut him down in the kitchen of his Spokane, Washington, house last December. Police say that Carlile’s murder was probably motivated by a series of complex business transactions that “went bad” in North Dakota’s oil fields.

Spurred by breakthroughs in horizontal drilling and hydraulic fracturing, or fracking, North Dakota now produces more than 1 million barrels of crude a day, surpassing OPEC members such as Qatar and Ecuador. The Bakken’s output, along with surges in Texas and elsewhere, has the United States poised to overtake Saudi Arabia next year as the world’s biggest source of crude. Where Teddy Roosevelt once hunted bison, drilling rigs and work camps now crowd the horizon.

Along with oil prosperity has come a spasm of crime unlike any before on the prairie. Where farmers once sealed deals with a handshake, authorities now contend with drug gangs, meth labs, violent crimes, prostitution and investor fraud, all with the same aim in mind: making a quick score.

“It’s like a gold mine,” said Troy Eckard, a Dallas-based asset manager who’s spent three decades arranging private-equity deals in the oil industry. “They are all just trying to see if they can hit a gold vein and get their money and run like hell.”

This account is based on three dozen interviews and a review of criminal, civil and bankruptcy cases in federal and state courts, as well as corporate filings. James Henrikson hasn’t been charged in the murder. He’s in custody in North Dakota on federal weapons charges unrelated to Carlile’s case. Henrikson has pleaded not guilty and faces a July 22 trial.

For Carlile, the Bakken represented the big score he’d never landed through years of new businesses and financial struggles. A devout Christian, he was a classic nice guy incapable of uttering a profanity even at work, said Reggie Olson, a trucker who knew Carlile. He and his wife, Elberta, raised six children, living on a 126-acre alfalfa farm in central Washington.

Over the years, he also branched out into trucking and construction businesses. Carlile, who was 63 at the time of his murder, filed for bankruptcy in 1999 after Washington state’s labor department secured nearly $100,000 in judgments against him. For years, he sought approval to subdivide his property for housing. When he finally got permission, the Great Recession hit.

“Doug was always kind of a big dreamer,” said contractor Pamp Maiers, who helped with the housing proposal. “He was good at everything except paying his bills.”

Henrikson was a different type - a young charmer with a bodybuilder’s physique, a pearly smile and a long rap sheet. Now 35, he grew up in central Oregon and over a decade was convicted there of crimes including theft, burglary, attempted assault, attempting to elude police and unlawful manufacture of marijuana.

Henrikson moved to central Washington at age 22, setting himself up with help from his parents as a mason contractor. He worked on large commercial projects and began a pattern of failing to pay into union benefits funds on behalf of his workers and running limited liability companies set up by his second wife, Stacey. She couldn’t be located for comment.

“There were always payroll problems,” said Tim Thompson, business manager for a bricklayers union in Washington. “It was always kind of a chase with this guy. He lies to people’s faces and smiles at them, and people buy it.”

Carlile’s widow, Elberta, told Spokane police that her husband met Henrikson about two years before the murder through Tim Scott, a building contractor in Ephrata, Washington. Scott knew both men through construction projects over the years and said he considered them good friends until, he said, Henrikson cheated him in a North Dakota trucking venture.

“James had a habit of burning every bridge he touched,” Scott said. “I told Doug, ‘Do not get involved with James.’ He said, ‘It’s my destiny, North Dakota’s my destiny.’ And it sure was.”

Henrikson and Carlile went in on two business ventures, a trucking company called Bridgewater Energy and an oilfield development firm, Kingdom Dynamics Enterprises. Henrikson helped Carlile and other partners buy an oil lease on 640 acres located within the Fort Berthold Indian Reservation for $2 million.

Financing was a problem. Henrikson and his third wife, Sarah Creveling, invested $640,000, and Carlile persuaded a friend from Spokane to kick in almost $1 million. The group still needed $400,000 to complete the lease purchase. After that, they needed someone who could drill a well for as much as $15 million.

By the time Henrikson and Carlile joined forces, Henrikson had already been doing business for about a year in the Bakken, setting up trucking businesses to haul crude and water and other loads for oil companies including Continental Resources Inc. and XTO Energy, an Exxon Mobil subsidiary.

Former partners who did oilfield work with Henrikson remember his eager, can-do attitude. On the road and in business meetings, he was often joined by Creveling, a petite, pretty blond from the Seattle suburbs. She kept the books for Henrikson’s businesses, according to a lawsuit filed by federal prosecutors to seize his assets. The couple married in August 2011.

In a business where dusty work boots and scuffed jeans are standard issue, the young couple stood out. Sarah favored fancy cowgirl boots and a fat diamond ring; James wore a leather jacket, designer jeans and tight T-shirts that showed off muscles sculpted in daily workouts.

“He was a go-getter, ambitious, clean-cut. They really did remind you of Ken and Barbie,” said Steve Kelly, whose company, Trustland Oilfield Services, subcontracted hauls to Henrikson.

Rolling around town in a hulking black pickup, Henrikson liked to stop in at a Watford City bar that featured a pricey cognac for Bakken high-rollers, acquaintances said.

“He just kind of exuded confidence,” said Amanda Kieson of Watford City, who contracted trucking work from Henrikson. “He’s got a big story and he knows how to tell it.”

He also had a reputation for cheating his partners, according to several people who worked with him. Kieson said she and her husband are still owed $100,000 for trucking work done for a company run by Henrikson and Creveling. Kelly said Henrikson began poaching his clients within days of being hired.

At one point, the businesses were pulling in $5 million a month, according to a former investor cited by prosecutors in the suit they filed against Henrikson in January. Even as they told investors they were losing money, Henrikson and his wife used some of the cash to buy a home in Watford City, two pickup trucks, a motocross bike and a Bentley Continental, purchased by Creveling for $60,099 with a cashier’s check, according to prosecutors.

The easy money didn’t last long. One source of the couple’s troubles was a determined mother named Jill Williams, who blamed Henrikson and Creveling on Facebook for the disappearance of her son, Kristopher Clarke, a former driver for Blackstone LLC, one of Henrikson’s companies. The couple filed a defamation lawsuit against Williams in Washington in October 2012, saying they had nothing to do with Clarke’s disappearance. They also said in court papers that bad PR resulted in the loss of their company’s largest client, an oil-services business owned by Tex Hall, the long-time chairman of North Dakota’s Fort Berthold Indian Reservation.

As Henrikson’s problems mounted, he focused on Carlile’s big strike, the 640-acre drilling deal. XTO, the Exxon Mobil subsidiary, owns rights on an adjacent parcel. Given the returns from neighboring wells, the land could hold “billions of dollars” worth of oil, said Stan Dedmon, a veteran Texas oilman whose money Carlile also sought.

“Geologically speaking, it’s an excellent project,” said Dedmon, who agreed to provide funding. “I’d rate it a Class A.”

By the summer of 2013, Henrikson’s past was closing in. The U.S. Postal Inspection Service, the Internal Revenue Service and the Homeland Security department were investigating possible wire fraud, mail fraud and money laundering by Henrikson and Creveling. Agents from the FBI and Bureau of Alcohol, Tobacco and Firearms later joined the probe into Henrikson’s activities.

Authorities began to piece together a violent cast of characters around Henrikson. One witness told police about a man who “was Henrikson’s muscle in North Dakota and would beat up or intimidate people.” Police also referred to Cooperative Individual .1, or CI.1, who worked for Henrikson and feared for his safety. CI.1 told police that he “personally heard Henrikson threaten to kill Carlile,” according to an affidavit.

Henrikson’s talk of violence included Hall, the Indian tribal leader, one witness told Spokane police. A Henrikson employee with “Mexican mafia” tattooed on the back of his head said Henrikson asked him in September “if he knew someone who would kill Tex Hall,” according to the affidavit.

Henrikson grew increasingly belligerent with Carlile, according to witness accounts detailed in a police affidavit. Around Labor Day, he showed up in Washington at the office of Carlile’s son, Skyler, and demanded $400,000. Skyler told police that Henrikson warned him “something bad could happen to me and my family” if Carlile didn’t find the money.

On Dec. 15, Doug and Elberta Carlile came home from church at around 7 o’clock in the evening. Elberta got out of their truck and went in the back door of the house while Carlile closed the black, wrought-iron gate over their driveway.

Elberta walked upstairs and then heard voices from the kitchen, according to an account she gave police. She came back downstairs to see a man dressed in black, with a facemask, pointing a large black semiautomatic handgun at her husband.

“Don’t do anything, don’t do anything,” Doug Carlile pleaded.

Elberta bolted up the stairs and heard five or six shots as she reached the top step. She hid in a closet and called 911. The gunman fled as Doug Carlile lay dead on the kitchen floor. Neighbors told police they saw a white van idling nearby.

Why was Doug Carlile killed? Spokane Police Chief Frank Straub said in a January news conference that the shooting was probably motivated by “business transactions that went bad” in the oil fields. Witnesses cited in police reports said Carlile and Henrikson were each trying to cut the other out of the drilling deal even as their finances threatened to dry up.

By mid-November, Henrikson had found another potential backer who said he’d invest only if Carlile pulled out. Carlile refused. He in turn was working on a plan to buy out Henrikson, witnesses told police.

On Jan. 14, 16 federal agents raided the North Dakota home of Henrikson and Creveling while the couple was out. Investigators said they were looking for evidence of fraud and of Henrikson possessing guns as a felon.

They seized 20 boxes of documents related to Blackstone and other companies and 20 digital data storage devices. They also headed for the 5-foot-high locked gun safe in the master bedroom. They called the safe manufacturer, who gave them the factory-set combination, which opened the door.

Agents found four pistols, two shotguns and an assault rifle inside the safe. They also found records for Blackstone and Kingdom Dynamics, Henrikson’s probation papers and court records from Oregon, and a Texas identification card.

The day of the raid, Spokane police charged a local man, 50-year-old Timothy Suckow, with first-degree murder. Suckow, a bald, burly felon with assault and burglary convictions, had dropped a glove behind the Carlile home that led to a DNA match, “a crucial piece of evidence,” said Straub. Police searched Suckow’s SUV and said they found a hand-written list with entries including “glove,” “wheel man,” “wipe tools down,” and “practice with pistol.”

Suckow’s lawyers have not commented on the list nor any other evidence.

When a second Spokane man, Robby Wahrer, was accused in April of driving the getaway van, the police affidavit cited an informant who said he told Suckow that “Henrikson was willing to pay $20,000 to do the job.”

On Jan. 18, police arrested Henrikson on charges of possessing weapons as a felon. He told arresting officers that he had “ties to organized crime from California,” postal inspector Thomas Irvin testified at his bail hearing.

Irvin also revealed an apparent rift between Henrikson and Creveling, saying: “She’s in fear for her safety and not returning home.”

Several days after the raid, Henrikson’s wife, Creveling, contacted federal agents, prosecutors said in an April 8 court filing. She told them that investors in their companies were defrauded through ownership transfers. Profits were funneled away from investors who received phony financial statements, Creveling said. She also said she bought guns for Henrikson, who would “meticulously” wipe them down to remove finger prints.

Five months after his arrest, Henrikson remains held at a squat, one-story jail in Rugby, North Dakota, on the eastern edge of the oil patch. Tim Purdon, the U.S. attorney for North Dakota, declined to discuss his case, as did authorities in Spokane.

Henrikson hasn’t been charged with murder. His former public defender in Bismarck, William Schmidt, said prosecutors told him a murder charge in the Spokane case was still likely. Henrikson’s current attorney, Thomas Tuntland, declined to comment. In Spokane, Suckow, the accused murderer, and Wahrer, the accused get-away driver, are in custody awaiting trial. Both have pleaded not guilty.

In the Bakken, plans are afoot to tap the Kingdom Dynamics land. Dedmon, the Texas oil man, said he’s lining up financing and hopes to start drilling by October. While lamenting Carlile’s death, he and the other investors are forging ahead on a project he figures could net $5 million a month in profit.

“The oil and gas industry is still a pretty two-fisted business,” Dedmon said. “There aren’t a lot of shy retiring types in this industry. But neither do you find guys who are willing to go out and sacrifice somebody else’s life.”

— With assistance from Joe Carroll.