On an August morning, 250 well-heeled San Diegans made their way to Qualcomm founder Irwin Jacobs’ La Jolla estate. Through one door, guests walked into an extensive modern art collection with a stunning David Hockney painting as its centerpiece. Through the other, they lined up to meet Democratic presidential frontrunner Hillary Clinton.

One of the most unlikely members of the crowd was Nash Habib, a small bull of a man who has admitted little interest in politics, but a lot of interest in money. He said he went to see Clinton – and paid $2,700 for the privilege – because he could.

“I donate a lot of money to things,” Habib said.

Luxury homes and big checks are far from the world Habib came from. Twenty-three years ago, he arrived in the United States as an Iraqi refugee. A decade later, Habib showed up in San Diego with an arrest warrant close on his heels.

But in the years since, Habib’s become the father of a towing empire, one that rivals the largest companies in San Diego’s cutthroat market. If you’ve had an accident on the highway, gotten arrested for DUI or called AAA to change your battery, it’s likely a towing company owned by Habib or one of his family members or ex-employees arrived to retrieve your car.

Hard work and Habib’s willingness to fight have fueled his rise. So has the inattention of local governments, which have responded to his repeated misstatements, evasions and overdue bills by awarding him lucrative contracts.

A big mystery also lies at the center of his success. Five years ago, Habib appeared to hit financial rock bottom after he lost his house to foreclosure and hundred-thousand dollar judgments against him rained down for unpaid loans and back taxes.

Today, Habib’s business has a fleet of new tow trucks, more than $3 million in property and enough disposable income to give some away to politicians. He won’t talk about where all the money came from.

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In the years after the end of the first Gulf War, streams of refugees from Iraq were trying to get to the United States. Habib was one of the lucky ones. He had missed the conflict, leaving Iraq when he was very young before making his way with his family to Greece, a country known for easing refugees’ path to the U.S.

Habib’s youth in Greece left a lasting impression. He gave his eldest son a Greek name, Angelo. Habib’s primary towing company in San Diego has the same name: Angelo’s Towing.

But when the opportunity arose for Habib to leave, he didn’t hesitate.

“Over there, everybody’s dream is to come to the United States,” Habib said. “You hit a jackpot.”

Habib landed in the U.S. the day he turned 18: Dec. 17, 1992. He had no education past elementary school, barely knew any English and struggled with reading and writing.

Habib, now 40, decided to begin his new life outside Detroit, long home to the country’s largest population of Iraqi Christian immigrants, known as Chaldeans, like him. Initially, the Chaldeans were lured by the good paying jobs in the auto industry. By the time those jobs went away, they had grown deep roots in the community.

Habib found work with cars, too, though not in the same way.

Twice in 1998, Habib was charged with automobile crimes, once for reporting an old BMW in his garage stolen when it wasn’t and the other time for running a chop shop to strip stolen cars and sell off their parts. He pleaded to lesser misdemeanor charges in both.

That same year, Habib was arrested and charged with beating someone with a tire iron and destroying a 1989 Oldsmobile. Two years later, he again faced assault charges, this time over hitting someone with a metal pipe. Both cases resulted in felonies for Habib, the first for busting up the car, the second for the assault. He violated his probation and eventually spent four months in jail.

When Habib got out, he went on probation again. By then, it was late 2002. Habib didn’t want to stick around Michigan much longer. His then-brother-in-law lived in San Diego, another region with a large and growing Chaldean population. Habib made his way here.

Habib didn’t tell his probation officer where he was going, and the Michigan Department of Corrections put out a warrant for his arrest.

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Soon after arriving in San Diego, Habib got a job as a tow truck driver at Rescue Towing. He quickly saved money to get his own truck and opened Angelo’s Towing along with two partners.

At the time, the San Diego towing industry was in a state of anarchy. A series of court rulings had thwarted local governments’ ability to stop tow trucks from trolling parking lots to snatch up cars from unsuspecting drivers. Towing companies took advantage.

“Once there’s no law in the town – and once the lawman’s scared of you – abuses tend to happen,” a local law professor told San Diego Magazine in 2007. “You saw it in the Wild West, and you saw it in San Diego in the early 2000s. Towing companies were definitely emboldened because of the state of the law.”

Even in the best of circumstances, people tend to be irate when their cars are towed. But when there aren’t any rules, you have the recipe for a powder keg. Habib was in the middle of it.

Less than a year after he started Angelo’s, a man accused Habib of pushing, threatening to shoot him and holding his car unless he paid an exorbitant amount of money, according to court records. In 2004, a rival towing company owner claimed Habib and two colleagues assaulted him outside a towing supply store with a chain binder. The rival owner said he was left with a deformed left eye and nose and a bleeding kidney. A lawsuit against Habib settled.

Nothing, however, compared to a vicious fight outside a Mission Beach tattoo parlor, an incident that revealed the worst in private property towing, racism and brutality.

Habib had a contract to tow cars from a Jack in the Box, and the tattoo parlor’s customers would often park in the restaurant’s lot. One afternoon in spring 2006, during a dark time in the Iraq war, a Marine parked at the Jack in the Box and went to get a tattoo with two of his friends. Soon after, a Chaldean Angelo’s employee arrived and hooked up the car.

When the Marine saw what was happening, he began yelling racist epithets at the tow truck driver. The argument escalated and the driver called Habib for help. Habib and another employee sped to the scene in a silver Escalade.

Habib marched into the tattoo parlor and called out the manager. By now, at least a half-dozen people were in the lot screaming at one another. The tattoo parlor manager, Habib later told police, called the Chaldeans “camel jockeys” and told them to go back to Iraq.

The manager stormed back to the store and returned with a wooden bat. It had “Implement of Destruction” written on the side. He started swinging.

Habib does not look like someone you want to fight. He’s short, but brawny with shoulders so broad it looks like he’s wearing a permanent set of football pads.

The melee lasted only 30 seconds. None of the Angelo’s employees was seriously injured, though the tattoo parlor manager ended up breaking the wooden bat over one worker’s arm. A tattoo parlor employee named Joseph Murphy wasn’t as lucky.

Murphy was wrestling with an Angelo’s employee when he was knocked to the ground. There, one of the Angelo’s employees kicked Murphy, knocking him out cold for five minutes. Murphy later needed plastic surgery to fix his face.

Neither the police nor a civil court judge could figure out whether Habib or another Angelo’s employee knocked out Murphy. The judge, however, determined that someone from Angelo’s did it and awarded Murphy $220,000 in damages – but after more legal wrangling, Murphy never saw any money from Angelo’s insurance company.

Around the time of the fight, there was lots of evidence that Habib’s career was on an upswing. He was able to buy out at least one of his partners in Angelo’s. He borrowed the first in a series of six-figure federal small business loans to raise capital. And he’d managed to resolve all his legal problems in Michigan.

But a dark cloud hung over it all.

Habib’s tow yard was in Barrio Logan. Before he opened up shop, a city employee assured him the land was zoned properly. Habib and his partners invested $1 million into the property.

But the city employee was wrong. A tow yard wasn’t allowed to be there. The city went after him and code enforcement fines piled up.

Habib pleaded his case to a hearing officer. Besides the bad advice, Habib said, the city’s pressure was ruining his business and creating family problems. Habib lost. In 2007, the city ultimately took him to court to make him pay.

A year later, on the eve of trial, Angelo’s filed for bankruptcy – though that case was thrown out shortly afterward. Still, that decision was the first in a series of moves that pointed to financial troubles. The bank soon foreclosed on Habib’s El Cajon home. Another bank sued him for not repaying the small business loans. He owed more than $100,000 in back taxes. By the looks of it, Habib was broke.

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Something good happened to Habib about four years ago.

This was after the foreclosure, the bad loans and the $100,000 tax bill. But it was before the six-bedroom, million-dollar home overlooking a golf course, the shiny fleet of new tow trucks and the major political donations.

Whatever occurred, it’s the key to unlocking how Habib went from a tow owner deeply in the red to the empire-builder he is today.

Habib won’t say how he amassed this wealth. Neither will anyone close to him. But what we do know is that no one has captured as much of the San Diego towing market as Habib in such a short time.

Today, Habib, his family members or his former employees, own at least parts of more than a half-dozen towing companies in San Diego. Their combined reach touches nearly every corner of the county.

Habib planted the seeds of this empire almost from the beginning. Angelo’s was just the first tow company that has his fingerprints on it.

Quality Towing came second in 2006. Next was Expedite Towing. Roadway Towing followed soon after.

The pattern worked like this. A towing company would start with the name of Habib, a relative or an address attached to Angelo’s. Then, through a series of small name changes and new corporate filings, ownership appeared to transfer to someone else. “Expedite Towing and Recovery” turned into “Expedite Towing” which turned into “Expedite Towing and Services.” Habib pulled the first papers for Expedite. Now the owner is listed as Nozad Shaba, one of Habib’s former employees.

This maze of corporate entities effectively conceals who has pieces of the towing companies and when Habib might have sold off any interest. More recently, Habib and his allies have started buying stakes of existing towing companies.

As Habib and his associates were growing their businesses, they turned to politics. In late 2009, Habib, his employees and related towing companies began throwing thousands of dollars at San Diego politicians, including the district attorney, the sheriff and multiple candidates for mayor.

Around the same time, Habib linked up with another ambitious young Chaldean named Mark Arabo. Arabo leads the Neighborhood Market Association, an organization of primarily Chaldean-owned corner grocers and liquor stores. Arabo was in the process of turning his group into a regional political force.

Arabo was one of the earliest and most effusive supporters of then-Assemblyman Nathan Fletcher’s 2012 mayoral campaign. The Neighborhood Market Association sponsored Fletcher’s primary election night party in June 2012 and Angelo’s and three Habib-affiliated tow companies co-hosted. It was a garish affair at a downtown hotel that had the podiums and pomp befitting a presidential candidate, but a lot of the air went out of the room when it became clear Fletcher was going to lose.

Habib’s political involvement only intensified from there. He gave to both remaining candidates in the 2012 mayoral election. Angelo’s wrote a $10,000 check to the right-leaning Lincoln Club. Habib said he hosted eventual mayoral winner Bob Filner at his house for a fundraiser.

Many of the donations connected to Habib have come under scrutiny. Habib’s low-level employees gave maximum allowable contributions to candidates the same days he did, which experts say could indicate that the donations were illegally laundered. City ethics regulators investigated Angelo’s, but declined to prosecute, citing insufficient evidence. A state inquiry remains ongoing.

In the towing world, big contracts with governments, insurance companies and groups like AAA are highly coveted. They provide exclusive, steady work from people who call the cops, drivers who break the law or in the case of insurance or AAA calls, from people who need help on the road. These towing contracts typically are much less hassle than grabbing cars from private parking lots – something Habib couldn’t stand.

“I hated that business,” he said. “It was a rip-off. For five minutes, you go into 7-11 and someone is there to take your car.”

So Habib started going after the big contracts. Now 95 percent of the 7,000 calls his tow trucks respond to each month come from his AAA contract, he said. The government contracts, Habib said, give him the prestige of working with the region’s top law enforcement agencies.

Habib’s political involvement began around the same time he was bidding on some of those contracts. He broke the rules to get them.

Each government agency required bidders to answer a series of questions about their backgrounds. Take a look at Habib’s responses to the city of San Diego in 2010.

Even if you excuse the city’s ignorance of Habib’s felonies, the bankruptcy and code enforcement fines would have been difficult to miss. At the time of Habib’s bid, the city had just ended a five-year code violation case against him. During that case, the city was formally notified of Angelo’s bankruptcy filing, which ended up being short-lived. A judge threw the bankruptcy out of court two weeks after Habib filed because he never attached the required financial statements. Habib eventually agreed to pay the city $10,000 to settle the code case.

But none of Angelo’s problems affected the company’s bid. It got a city contract. Similar misstatements littered successful applications for contracts with the California Highway Patrol and the Sheriff’s Department. There’s no indication Angelo’s has been punished for any of them, even when the business got caught.

In 2012, the city prosecuted Habib and his wife for failing to disclose his entire criminal history to the CHP. Habib had told the CHP about previous cases but not their severity. Habib told investigators he didn’t know the difference between a misdemeanor and a felony. Ultimately, the city dropped the charges against Habib. His wife, who filled out the CHP forms, ended up pleading to a misdemeanor for knowingly concealing a material fact from the agency. Afterward, the CHP kept Angelo’s on its towing rotation.

Scott Chadwick, the city of San Diego’s chief operating officer, said city officials were unaware of the extent of the concerns involving Angelo’s until I contacted them for this story, even though the city had acted against the company many separate times.

“Different departments knew components of this, but there was no coordination in the process,” Chadwick said.

The city expects to complete an investigation into all of Angelo’s issues in the coming weeks, Chadwick said.

Habib won’t talk much about the misstatements in his government contract applications, either. He and I spoke in advance of my September story on questionable political donations from Angelo’s and other towing companies. But he demurred when I asked to talk more about his background and rise.

“I am not interested in publicity of this nature for myself or for my company, and prefer to focus my attention on taking care of my business and my clients,” Habib told me. He asked me not to contact him or anyone else at Angelo’s again.

On the eve of this story’s publication, I sent another email to Habib detailing everything I planned to include in the piece. An attorney from powerful local law firm Seltzer Caplan replied, pleading for time to respond. Three weeks later, we were told Alan Ziegaus, the chairman of Southwest Strategies public relations firm, and a colleague of Ziegaus would talk with us about Habib.

“Mr. Habib is very firm he’s never been convicted of a felony and we think that that’s a wrong assertion,” Ziegaus said at the beginning of the meeting.

We presented Ziegaus with documents showing Habib’s criminal history and Ziegaus promptly ended the interview.

In my first interview with Habib, he told me he wants to grow stronger. Habib told me he was considering creating a formal association of the towing companies in his empire to fight for even more business.

Right now, Habib’s beef is with the city of Chula Vista.

That city has delayed putting its towing contract out to bid, and Habib blamed the influence of the region’s more established companies for wanting to shut him out.

“It’s just not fair,” he said.

Habib does use a tow yard out of Chula Vista now, though. Four years ago, that city cited him for operating the yard without city approval and for building an office without a permit. He still hasn’t resolved everything. Habib owes the city of Chula Vista more than $20,000 and the fines are growing by the day.