It started with a Facebook message: “What’s up beautiful?”

Acacia Oudinot wouldn’t usually respond to an unsolicited Facebook note—especially from a strange man complimenting her appearance. A striking 37-year-old divorcee from Arizona, Oudinot is used to men hitting on her and adept at brushing them off. But something about Will Jackson intrigued her. Maybe it was his smile or his stylish outfits. Maybe it was the fact that they had mutual friends. Either way, she decided to message him back a single word: “Hello.”

It was a decision she would deeply regret—and one, she would later learn, many others had regretted before her.

Over the following weeks, Oudinot and Jackson texted, spoke on the phone, and FaceTimed. He loved football, and she was crazy for the Oregon Ducks. He asked about her travels and about her nine years in the Air Force. When a close friend deserted her on Christmas, Jackson offered to fly Oudinot to Los Angeles to take her mind off things. The suggestion sounded crazy, but her friend told her to go for it. “You never do anything spontaneous,” Oudinot remembers her saying.

When she finally agreed, Jackson sent her a screenshot of her boarding pass. But when she arrived at the airport that weekend, officials told her the ticket was invalid. She called Jackson, who insisted the tickets were good. But the clock was ticking and the flight was boarding soon. Jackson told her to purchase a ticket at the airport and promised to reimburse her when she arrived. He even sent her a selfie from the bank, claiming he was trying to work it out.

Oudinot got into L.A. late that night, so Jackson picked her up from the airport and took her to the movies. He was sweet and doting, asking about her career and dreams for the future. He told her he had two children but wanted more. On Saturday morning, he cooked her breakfast—bacon, eggs, and grits—and drove her back to the airport. He texted her Sunday just to say good morning.

On Monday, Oudinot woke up to nearly $3,000 missing from her account. There was a charge for a fast food restaurant, a transfer for $2,500, and one airline ticket booked from Dallas to Los Angeles, according to interviews and a police report.

Instantly, Oudinot knew it must have been Jackson. Her cards were still in her purse, but the charges were from California. Jackson was the only person she had seen in L.A. And he had already blocked her number from messages and calls.

When she called the police, they were less than helpful. Scottsdale told her to report the incident to Los Angeles, which told her to report it to Scottsdale. So Oudinot started investigating on her own.

She couldn’t remember Jackson’s address, but she got the fast food restaurant’s address from her bank. From there, she used whatever details she could remember to narrow down the nearby apartments. She searched for buildings that were tall (they’d parked in an underground garage), on a busy street (it had been noisy), and close to a movie theater. When she found the likely location, she googled the floor plans to confirm. But when she called the building to ask if a Will Jackson was living there, they said no.

“And then it dawned on me then and there, ‘Oh, I don't even know who this guy is,’” she said.

Jackson had already blocked her on social media, so Oudinot enlisted her friends to go on his public profile and download his pictures. She conducted reverse Google image searches—a technique she learned from the MTV show Catfish—until one of them turned up a result. It was linked to a social media account in a different name, which led to an email account listed under Syncere Jackson.

A Google search for that name turned up an 85-word article in the West Orlando News. It said police were looking for victims of a man named “Syncere,” who befriended single women on Facebook, gained their trust, then drained their bank accounts. The article was from 2011. And it had a mugshot.

“I saw his picture and I was like, ‘Holy shit,’” she said.

Will Jackson, aka Syncere Jackson, aka “Da Truooth”—real name Wilson Edward Jackson—was born in Daytona Beach, Florida, to a strict, religious family. He left the state briefly to attend Dodge Community College in Kansas, but returned around 2002 with the intent of enrolling at the University of Florida. He told friends he was pursuing a rap career and told girlfriends he was playing football. Most police reports from the time list him as unemployed.

In the decade that followed, according to court records, Jackson bounced between Tallahassee and Orlando, staying with girlfriends and getting evicted from a different apartment almost every year. One friend, Kristina Palmer, says he convinced her to sign on as a guarantor for his lease, then moved out early without paying rent. According to court records, Palmer was left to pay off the debt. Later, Palmer told police, Jackson used her personal information from the lease to apply for credit and try to purchase a car.

What Wilson didn’t have in rap skills or cash, he made up for in charm. He was 6-foot-1, with an athlete’s build, and always immaculately dressed. He decked himself out in brand names and pricey jewelry. He made a point of looking put-together, former girlfriends said, even if he’d just rolled out of bed. But he was also a great listener—someone who seemed genuinely interested in his girlfriends and their problems. Palmer said he could make you feel “like you’re the most beautiful thing in the world.”

“In that moment that you were with him, you almost felt like you were the most important thing to him,” she said. “He knew how to charm somebody, I’ll tell you that much.”

But there was also an edgier side to his appeal. Shondra Porter*, who dated Jackson in 2007, said he reminded her of a snake, a slippery swain who could “shed his skin and morph into somebody else” at any moment. She remembers a tattoo on his back that read “OUTLAW” in bold letters. It struck her as amusing at the time, given his conservative upbringing. In retrospect, she thinks it hinted at something more sinister.

“I’m really thinking that this was his goal,” Porter said. “He wanted his face in the news. He wanted this to happen. Because he literally felt as if he was this outlaw.”

In the early 2000s, according to police reports and victim statements, Wilson started channeling his womanizing skills into a money-making scheme: bedding or befriending women, then stealing whatever he could find from their apartments—rings, credit cards, check books, $40 cash. In other cases, he sweet-talked women into lending him money, then never paid them back.

According to one police report, Jackson bought nearly $1,000 worth of plane tickets on a girlfriend’s credit card, then insisted she had authorized it. In another, he met a woman at a bar, stole and used her credit card, then returned it on their second date. In both cases, he was ultimately ordered to pay the women back.

The Daily Beast reached out to Jackson’s mother, sister, and five attorneys who represented him in various cases across Florida, but none of them had any comment. Jackson’s public defender did not return calls and emails.

In 2011, Jackson met 22-year-old Neish, who asked that her last name not be used, during her homecoming weekend at Texas A&M. They began talking on the phone regularly, sharing intimate details of their lives. Neish had recently been diagnosed with cancer and was undergoing chemotherapy at a local hospital. She had no family in the area and often felt lonely and afraid. Jackson, she said, seemed interested and sympathetic.

Months later, when he moved back to Orlando, she says Jackson called her to ask a favor. He’d left his bank card at a hotel and needed cash. Someone could deposit a check in her account, he said, and all she had to do was wire the money to him. She says he stressed the need for urgency, so when she saw the check deposited in her account, she rushed to a Western Union to send him $1,900.

Later that day, Neish went to get her nails done as a pick-me-up after a particularly rough week. She called her bank as a precaution, to make sure she had enough money to cover the manicure, and was shocked when they told her the account was overdrawn. Someone had deposited the check in her account, they told her, but it bounced. When she texted and called Jackson about the situation, she said, he ghosted.

Neish reported the incident to the police, who said they’d been getting complaints about Jackson for years. But there was nothing they could do in her case, they told her: She’d sent the money of her own volition. “Of course I felt dumb and stupid,” she said. “They pretty much made me feel like there was nothing that could be done.”

Years later, when she found out there were other women in her situation, she said, “it kind of made me feel relieved, like I wasn’t the only one who fell for this stupid trick.”

In fact, dozens of women would fall for Jackson's alleged tricks. In the decade between 2002 and 2012, he racked up 75 charges in three different counties. Nearly half were for felonies, ranging from fraudulent use of a credit card to grand theft. A former public defender who represented Jackson told The Daily Beast it was one of the longest rap sheets he had ever seen.

“ He’s using his intelligence for evil. ” — Brian Kramer

Still, Jackson never spent a day in state prison. His longest county jail stint was less than a year. Of his four criminal felony charges in Orange County, Florida, none ever made it to trial. Forged checks were paid off; plea deals were accepted. Police—despite Jackson’s prolific criminal history and victims’ sworn statements—dropped cases for a “lack of investigative leads.”

Brian Kramer, an assistant district attorney in Alachua County who was not involved in any of the cases, told The Daily Beast he's not surprised Jackson never did hard time. Financial crimes are considered low-priority in Florida, which uses a point system to determine sentences. Since these kinds of crimes are so often motivated by poverty, Kramer said, judges tend to be more lenient.

Jackson often played off this sympathy, telling judges he “started off with nothing” and now had children and a college education to attend to. The University of Florida—which Jackson claimed he attended—says he was never enrolled. Porter says he has only seen the child she had by him once.

Kramer said the Florida sentencing structure could be “a little frustrating,” especially when dealing with people like Jackson. “[He] obviously has some level of sophistication because this is not just a snatch and grab,” Kramer said of the punishment guidelines. “He’s using his intelligence for evil.”

But by 2014, things had gotten a little too hot in Florida, even for Jackson. His exes had started networking on social media, reaching out to his new girlfriends and warning them—and in some cases their parents—about his behavior. Neish had written a blog post that was attracting comments from other victims. Some women started a MySpace page to commiserate about how they had been scammed. Richard Campbell, the father of one of his ex-girlfriends, started reporting Jackson's every move to his probation officer.

So, just as quickly as he came into their lives, Jackson packed up his bags and left for California.

“He’s a con man,” Campbell mused. “You never could put your finger on him.”

By the time Oudinot called Stephanie Krachjir at the LAPD in 2018, the detective had already been tracking Jackson for years. An overworked 55-year-old veteran in the Commercial Crimes Bureau, Krajchir first became interested in Jackson in 2016, when several women reported him for theft or fraud. When Krachjir looked him up in the city’s law-enforcement database, she could see other agencies had received reports of Jackson forging checks. She made a mental note to follow him and started a file on her already-crowded desk. She also left a comment on a West Orlando News article asking victims to call.

When Oudinot called Krajchir about that comment nearly two years later, the detective told her about the stack of records on her desk. She said Jackson had evaded arrest for years, skating by on overworked officers and women too nervous to report. If they wanted to nail him for any meaningful amount of time, she said, they would need at least two more victims.

Oudinot took that as a challenge. Her job new would not start for months, and she was—as she put it—”slightly obsessed” with the case. She posted to Facebook asking other victims to reach out with information. She spent her free time digging through Instagram, LinkedIn, and comments on the West Orlando News article. She called banks, airlines and credit card companies for names, using the same investigative skills she'd used to find Jackson to track down the women he wronged.

In the end, it was this network that brought Jackson down. Oudinot found Neish through her blog post, and identified other victims through the comments section. She used the plane ticket Jackson bought on her credit card to find his next victim—a female police officer from Dallas. She isn’t even sure how she met Porter, but it must have been through one woman, who told her to talk to another woman, who told her to talk to another.

Kiara Miller*, a 28-year-old from Southern California, reached out to Oudinot on her own. In February 2018, Jackson took Miller on a date and told her he was having trouble with his bank card. He asked her to deposit two checks into her account and wire him the money—the same scheme he’d used with Neish years before. Miller said the checks belonged to a woman, but looked like they had been made out in Jackson’s hand. When she went to deposit them, the bank told her they were on hold. She sensed something was wrong and decided to call the woman whose name was on the checks: Acacia Oudinot.

On Jan. 8, when Oudinot first called the LAPD, Krajchir had eight victims. By February, she had 18.

“She was awesome,” Krajchir said of Oudinot. “She really was.”

The victims became close over the course of the investigation, setting up group chats that stretched from Florida to Arizona to Texas to California. But as time wore on, the investigation stalled. Krajchir had promised an arrest by April 2018, but she was slammed with more pressing cases. April, May, and June went by with no developments. When Oudinot left for Afghanistan in November—she still works stints as a civilian air traffic controller—the case’s most vocal advocate was suddenly gone.

In January of this year, as Oudinot was returning from her travels, she realized it was the one-year anniversary of her ill-fated date. Still, no arrests had been made. Even worse, she knew Krajchir planned on retiring soon. Too many times, Jackson had slipped through cracks left by transitioning between officials: retiring detectives, rotating probation officers, fresh-faced attorneys. Oudinot couldn’t let that happen again.

So in February, she called Krajchir and gave her a warning: She wanted an arrest by April 1, or she would file a complaint against the detective.

At the end of March, just days before the deadline, Krajchir was performing a routine check on Jackson when she noticed he had been arrested by California Highway Patrol for auto theft. There was no mention in the arrest warrant of any financial crimes. Krajchir quickly phoned the CHP detective. Would he be at Jackson’s next court appearance? They needed to talk.

In January 2019, Jackson—using the name “Will” instead of Wilson—had convinced a San Jose woman named Ana Martinez* to visit him in Los Angeles. But when he picked her up at the airport, he claimed he couldn’t get a rental car because of a problem with his credit card. Martinez volunteered to cover the cost, assuming he’d pay her back later. They went out to dinner and back to his apartment for a nightcap, which made her drift off to sleep.

The next morning, Martinez says, Jackson started acting strange. He kept saying he had things to do and urging her to leave quickly. When Martinez didn’t move fast enough, she says, Jackson simply hopped in the car and drove away. Shocked, she called an Uber and headed to the airport. She called the rental car company when she got home to see if Jackson had returned the car. He had not.

As a precaution, Martinez decided to cancel all of her credit cards but one. Sure enough, she says, Jackson used that card to fly another woman from Chicago to Los Angeles days later. He also bought gift cards, movie tickets, and a Netflix subscription that led Martinez to his real name. Once she had his true identity, she did what other women had done before her: She googled him, and realized what she was dealing with.

The investigators at the rental car company had been less than helpful, so Martinez’s sister decided to post on Facebook as a warning to other women. A week or two later, a woman from Las Vegas messaged her to say that she, too, was a victim of Jackson’s scam. He had flown her to his apartment that weekend, and she had seen Martinez’s rental car parked outside. She even took a picture and sent it to her.

Evidence in hand, the sisters decided to go straight to the LAPD. The detective on the case told them he was waiting for the right time to make the arrest. The sisters kept calling for updates, week after week, until one day the detective abruptly hung up on them. Fifteen minutes later, he called back. They had the car, he said, and Jackson had been arrested.

In person, Jackson is as charming as his accusers describe. Even from behind a pane of glass at the Pitchess Detention Center outside Los Angeles, he seemed confident and flirtatious, sporting a playful smile and his signature silver nose stud. He was also adamant that the charges against him were false.

“It’s not true,” he said repeatedly. “It’s just accusations.”

Jackson admitted that in college he was more focused on getting himself ahead than on the women he dated. But these days, he said, he’s all about lifting women up. He pointed to his Instagram page, where he posts messages like “Lust expires, get yourself a girl that prays for you,” and “We gotta make being faithful to one woman cool again like 90’s R&B songs.” One quote held a note of irony: “Having the right woman in your life is like printing your own money.”

As for the charges, he claims the women willingly gave him the things they now say he stole. Martinez was the one who left the rental car at his house, he said, and he’d been trying to get the company to pick it up for weeks. His story: He was on his way to return it himself when he was arrested.

Jackson also accused Krachjir of harassing his family and claimed she had no evidence or warrant for his arrest. He questioned why some women had waited so long to report. “If a woman was victimized, why didn’t she come forward before?” he asked.

Once again, Jackson claimed he attended the University of Florida, which has no record of his enrollment. He also claimed to run a solar energy business called Jackson Energy Enterprises. A search for the company turned up an Instagram profile with 89 followers, consisting largely of re-posts from Jackson's personal account. The profile linked to a site for a generic solar panel company. There is no "Jackson Energy" in California Secretary of State records.

“ If a woman was victimized, why didn’t she come forward before? ” — Wilson Jackson

When Jackson walked into court on May 23, he was facing two felony charges for the theft of the rental car. By the time he left, Krajchir and the LAPD had slapped on 20 more counts. There are eight victims in the complaint, but Krajchir said she’s heard from nearly 50. She estimates their combined losses total more than $200,000.

Talking about the case these days, Krajchir sounds satisfied but exhausted. She is one of only a handful of financial crimes detectives in the entire county, probing everything from Armenian racketeering rings to rent-dodging dentists. She credits the women for their persistence in moving the case forward, and even praised Oudinot for motivating her with the threat of a formal complaint.

Still, she regrets how long it took the case to come to fruition.

“It wasn’t fair,” she said in an interview. “It wasn’t fair that all this went on because we couldn't get to a case.

There is also the uncomfortable fact that, after decades of scamming black women, Jackson was only arrested after ripping off a white woman. While many of the victims credit Oudinot for the months of work she put into the case, some acknowledge that it may not have been a coincidence.

“Acacia was the only one that said, ‘If you don't do something, I’m going to speak to your supervisor,” Miller said. “People of color already feel like police aren't going to help them. So if they don’t do something right away, they get discouraged and say, ‘They’re not going to do anything.’”

Jackson has a preliminary court hearing set for July. His first attorney, Chanel Shackelford, quit the case after his payment check bounced. The judge has ordered him to have a public defender and held his bail at $300,000. On the night of his arrest, Jackson was supposed to go on a second date with yet another woman he met online. Instead, he called her for bail money. After seeing reports of his arrest, she turned him down.

“If it wasn’t for you and your strength to go after him, I could have possibly been a victim,” she wrote in a message to Oudinot. “So thank you! I wish you all the best and I hope he gets everything he deserves.”

Porter, the former girlfriend from Orlando, said she’s just happy Jackson’s face is in the news, so that other people can’t be scammed. But she also can’t shake the feeling—the one from more than a decade ago—that this is what Jackson wanted: to be splashed across the newspapers; a famous outlaw.

Shackelford said Jackson seemed unnervingly calm, even confident, in his meetings with her. According to his Instagram account, he is planning on writing a book. When he appeared in court the first time, Oudinot said, he smiled at her.

*Pseudonyms were used for names marked with an asterisk at the request of the victims.

Additional reporting by Tarpley Hitt