Butch Ward, the dean of the Jefferson Parish Council, expected an easy ride to re-election in 1999. But Shane Guidry, a little-known businessman with access to a big bank account, had other plans.

Guidry waged the most expensive and perhaps the nastiest race for a Jefferson Parish district council seat ever seen, spending $2 million of his own money — much of it on attack ads — to try to win a job that paid only $46,000 per year.

Ward thumped him.

Guidry shook off the loss to grow a former family business that he now runs and partly owns, Harvey Gulf International Marine, into a major supplier for oil and gas companies drilling in deep waters, although the drop in oil prices since 2014 has forced the company to sharply downsize.

Lately, Guidry has re-emerged in Louisiana politics, but now he’s spending big on other people’s campaigns. He and Harvey Gulf are writing big checks — $244,000, the maximum allowed, to the leadership fund of U.S. Rep. Steve Scalise in 2017; $100,000 to a super PAC that backed Jeff Landry when he was elected attorney general in 2015; $85,000 to a super PAC that attacked Scott Angelle in a 2016 congressional race; and $33,900 to the National Republican Senatorial Committee in 2017.

And all of that paled next to the $500,000 his company donated to the January inauguration of President Donald Trump, making it the biggest single Louisiana contributor to that event. Guidry also raised $1 million for former Florida Gov. Jeb Bush during his aborted 2016 presidential campaign.

Guidry and his company together may be the most potent fundraisers in Louisiana Republican circles today. He is a fervent conservative who believes that former President Barack Obama divided the country and weakened the military.

“I want to see the Washington swamp drained,” Guidry said in an email. “Lower taxes, more jobs, a safer country, stronger military and fiscal responsibility.”

He added, “I've wanted to see a successful business person in the White House for a long time. Now, we have it. If the left-wing media would report only true facts, we'd all be able to see just how good President Trump is really doing.”

Guidry, 47, initially agreed to an interview with The Advocate but after he said he met with his legal team, he answered questions only by email.

Guidry played on both sides of the 2015 governor’s race. In 2014, Harvey Gulf contributed $50,000 to the Fund for Louisiana’s Future, a super PAC that backed then-U.S. Sen. David Vitter, the Republican who went on to lose the runoff to John Bel Edwards, a Democrat.

Nearly a year later, Harvey Gulf donated $100,000 to Gumbo PAC, which was created by a Democratic campaign operative to attack Vitter during the race. One Gumbo PAC television ad featured Jefferson Parish Sheriff Newell Normand, who is close to Guidry, telling viewers that Vitter, a fellow Republican, was unfit to become governor.

Guidry said he couldn’t remember who asked him to make the contribution to Gumbo PAC. He didn’t answer a question about why he contributed to the PAC.

Close to Landry

While he supports many politicians with checks, Guidry is particularly close to Landry. Harvey Gulf donated $100,000 to Louisiana Citizens for Job Creators, a super PAC that backed Landry’s 2015 election campaign, and gave $25,000 in 2016 to the Louisiana Committee for a Republican Majority, a super PAC chaired by Landry.

Guidry has squired Landry around in his corporate jet, now a Falcon 2000. In a very unusual arrangement, he also holds a senior position in Landry’s office — all while running Harvey Gulf, which under him has grown to be a major player in the offshore oilfield supply business.

The company’s vessels carry workers and cargo, including liquid natural gas, to offshore oil rigs and can supply teams of workers — and even a helicopter — for offshore construction projects.

At the Attorney General’s Office, Guidry initially took a modest salary of $12,000 a year, but he said he now performs his work on a pro bono basis.

Guidry also has ties to U.S. Sen. Bill Cassidy: He is one of eight people on a panel helping Cassidy vet candidates for vacant federal judgeships and Louisiana's three U.S. attorney positions.

Harvey Gulf has also been in the news for its business dealings with Normand and another powerful Jefferson Parish elected official, state Rep. Cameron Henry, R-Metairie. The company purchases some supplies from a company recently started by Henry, a Landry ally who chairs the House Appropriations Committee. Normand, meanwhile, co-owns a firm that gets paid sales commissions on all items that Harvey Gulf orders through an offshore supply company.

For both Normand and Henry, offshore supply is a side gig rather than their primary line of work, and it’s not clear how many other clients they have. Both Guidry and Normand have said the transactions are not unusual. Henry did not respond to a request for comment.

Normand’s business partner Craig Taffaro, his former chief deputy, was recently indicted in federal court. He is accused of avoiding taxes owed on some of his income from CTNN Enterprises, the supply company he co-owns with Normand.

Normand has said Taffaro’s tax charges, which Taffaro’s attorney has said he will fight, are his former deputy’s own business and have nothing to do with the sheriff.

People who know Guidry describe him as a shrewd, tough and hands-on businessman who has succeeded despite dropping out of college.

“He understands balance sheets,” Normand said in a brief interview, declining to say much more without talking first with Guidry.

Boysie Bollinger, a major Republican donor whose family sold Bollinger Shipyard in 2014, has known Shane Guidry for years. Bollinger Shipyard sold an offshore supply boat business called BeeMar to Harvey Gulf in 2012 for a reported $243 million.

“We describe him as a street fighter,” Bollinger said. “He always survives. I wouldn’t bet against him.”

A disappearing oak

Understatement appears not to be part of Guidry’s vocabulary.

In the 1990s, he owned the flashiest house in the Stonebridge subdivision in Gretna, one that caught the attention of golfers on the first hole of the country club there.

Now he owns the most ostentatious house in Old Metairie. He paid $1.2 million for the lot and spent many millions more to build an 18,000-square-foot home, complete with a private spa, gym and movie theater. Guidry has hosted fundraisers there for Scalise and former Jefferson Parish President John Young, among other Republicans, according to public records.

The house is something of a local landmark not only for its size but because an oak tree that Guidry wanted to remove — but hadn’t won approval to do — disappeared one night. Neighbors were furious. Guidry said he believed one of the neighbors was responsible.

“The neighborhood is filled with a bunch of old, wannabe blue bloods, who feel guilty about their inheritance and/or the trust funds they live on,” he said. “So, they attack hard-working job creators like myself.”

This summer, in keeping with his outsized tastes, he rented what is believed to be the largest house in central Aspen, Colorado, a house previously rented by billionaire Bill Gates.

The arc of Guidry’s career begins with his father, Robert Guidry, known as Bobby, whose story in turn began with his father, Numa, who moved from New Orleans to Galliano in the 1950s to become an oysterman. In time, Numa assembled a fleet of vessels to tow barges along the coast. Bobby Guidry eventually took over the business, and he insisted that his children learn it from the ground up.

But Bobby Guidry had bigger ambitions. He wanted a license to operate one of the new riverboat casinos to be awarded by a state board appointed by Edwin Edwards, then in his fourth and final term as governor. Through a friend’s introduction, he began playing in a notorious Thursday poker game at the Governor’s Mansion hosted by Edwards. In 1993, Bobby Guidry received one of the 15 coveted licenses and opened the Treasure Chest casino on Lake Pontchartrain in Kenner.

In 1998, Bobby Guidry pleaded guilty to paying $1.4 million to Edwards and two others to win the license. He was a star witness at the trial in 2000 when the former governor was found guilty of racketeering, extortion, money laundering, mail fraud and wire fraud; he testified that he often left the governor and his son cash bundles of $100,000 in unlikely places, including Dumpsters.

For his key role in securing Edwards' conviction, federal authorities allowed Bobby Guidry to keep the $80 million he had collected from selling the Treasure Chest. They also allowed him to spend no time in prison.

Bobby Guidry did not return a phone call seeking comment for this story. (Even though Bobby Guidry helped send Edwin Edwards to federal prison for 10 years, the four-time governor invited Shane Guidry and his wife to his 90th birthday party on Aug. 12 in Baton Rouge. They were among the 500 people who paid $250 apiece to attend. “Edwin is a friend,” Shane Guidry said.)

'Shame, Shame, Shane'

While Guidry was running for office in 1999, The Times-Picayune reported, he first said he hadn’t owned a share of the casino boat, but then acknowledged that he had. He also changed his story to admit that he had received immunity to testify before a federal grand jury, the newspaper reported.

Guidry made the admissions while he was attacking Ward and vastly outspending the council veteran for the District 1 seat, representing Terrytown and Gretna.

The acknowledgements opened the door for Ward to launch a memorable radio ad.

Listeners heard a takeoff on “Chain of Fools,” the Aretha Franklin classic. The new refrain went “Shame, Shame, Shane” and hammered Guidry for altering what he had said. In a recent interview, Ward said that when he would meet with voters, they would begin singing the campaign jingle.

Guidry counted on the strong support of then-Sheriff Harry Lee, who owned land with Bobby Guidry. Then a Democrat, one of Shane Guidry’s mailers to voters showed him alongside President Bill Clinton and U.S. Rep. Bill Jefferson of New Orleans, both Democrats.

Guidry countered Ward’s radio ad with a television ad that claimed — falsely, according to then-New Orleans Mayor Marc Morial and Jefferson Parish President Tim Coulon — that Jefferson Parish had given a sweetheart deal to Ward’s brother to open the River Birch landfill and that New Orleans was sending garbage to it.

Butch Ward won, 61 percent to 39 percent.

Asked in retrospect whether he regretted his attacks against Ward, Guidry said, “No. He and his associates were running the West Bank for personal gain.”

Shane Guidry said he started at Harvey Gulf when he was 12, and his father had him spend summers working for the company. He graduated from De La Salle High School in New Orleans and attended Holy Cross College and Nicholls State University but dropped out to work for Harvey Gulf full time.

“It was at a time when the business was growing, and my dad was teaching me much more than college could,” he said.

Guidry said he took over running the business in 1994, when his father shifted his focus to the Treasure Chest.

After losing the 1999 race for the Jefferson Parish Council, Guidry moved to Houston because, he said, his business “had taken off, and the majority of my clients were there.”

In 2008, with Guidry living again in Louisiana, tension was rising to a boil with family members who worked in the business.

“They only worked when they wanted to work. I worked seven days a week, 18 hours a day, and, frankly, didn't want to be questioned or fight with family,” Guidry said. “They did not live the life I had to live — giving up/leaving my wife and kids every week, night after night, and never being there for the kids. So, their questioning me, why I did things the way I did, did not work for me.”

Guidry negotiated the sale of Harvey Gulf to the Jordan Company, a New York-based private equity firm that owns a number of businesses. “The offer was huge for the assets we owned and the direction the business was going in,” Guidry said.

The sale brought the family hundreds of millions of dollars. Jordan retained Guidry and gave him a 23 percent ownership share, a bigger share than he had before. This development led to a bitter split between him and his father.

“My dad, who I love more than anyone, just comes from a different time and didn’t understand,” Shane Guidry said. “He comes from a place and time where you just abandon your kids in a heartbeat over money.”

Shane Guidry said he and his father haven’t spoken in seven years.

'I make all decisions'

Guidry operates from a 37th-floor office in One Shell Square. Models of his vessels line the public space by the elevators.

Instead of using a traditional desk, he sits at the head of a glass conference table; his top executives frequently fill the surrounding white plush chairs.

A giant-screen TV at the end of the table was tuned to Fox News on a recent afternoon. “Trust Betrayed: Barack Obama, Hillary Clinton, and the Selling Out of America's National Security,” a 2015 book written by a former Navy SEAL, lay on the desk.

In recent years, Harvey Gulf has suffered with the drop in oil prices and the overall decline in offshore drilling. Guidry said he has had to lay off 1,000 employees since 2014 and now has about 600.

“We've all taken a hit,” he said. “We've all lost business.”

But he said the company continues to perform better than other, bigger companies.

“I know every inch of what I own and how to operate every aspect of it,” he said. “I'm involved in every single part of my businesses. I make every decision over $1,000 in value seven days a week. I'm never top-heavy. I make all decisions and know all my clients, personally.”

Guidry seems to have a particular fascination with law enforcement. He spent more than 23 years as a part-time, reserve Jefferson Parish Sheriff’s Office deputy, patrolling the streets. He eventually rose to become a chief in the reserves before resigning in 2016.

Guidry said he got to know Landry while tailgating before LSU football games, and he later hired Landry as an attorney to help him obtain operating permits at Port Fourchon, after Landry had served one term in Congress but before his election as attorney general.

After Landry took office, Guidry said he went to work to “rebrand and reorganize the law enforcement division” in the Attorney General’s Office.

“I rebranded the unit to become the LBI, Louisiana Bureau of Investigation,” Guidry said. “I instituted new hiring practices and procedures which resulted in new, very seasoned agents.”

He worked for $1,000 a month — a token amount — as a “special assistant to the attorney general.” Since June, Guidry said, he has served Landry on a volunteer basis.

Guidry made news in mid-July for helping broker a political truce between Landry and Gov. Edwards, who have been feuding.

Landry declined to answer questions from The Advocate, including about his travels with Guidry.

“His work has helped our office to cut costs and reduce waste and to more efficiently and aggressively combat crime,” Landry said in an email, though he did not provide examples.

Guidry and Normand served as co-chairs of Landry’s transition team. But the sheriff and the attorney general have been at odds over Normand’s refusal to have his deputies seek out and arrest potential illegal immigrants, in defiance of a demand by the Trump administration that Landry backs.

Normand said that has not strained his relationship with Guidry.

“He has his politics, I have mine,” Normand said. “I’ve never let politics get in the way of a friendship.”

Guidry said the political differences between Landry and Normand played no role in his decision to resign as a reserve deputy sheriff last year.

“I just didn't have time to do both,” he said. “But let me be clear. One reason I've achieved the success I have to date is that I can separate business, personal life and politics.”

Follow Tyler Bridges on Twitter, @tegbridges.