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Jessica Stilwell’s Inspiring Comeback

Jessica Stilwell has spent the last few years trying to avoid a day like today.

And it’s really no shock as to why.

The 39-year-old was in the public eye for more than a decade, first as a popular NBC-2 anchor who wowed viewers with her genuine personality and friendly face and later as the shamed wife of a man who was sent to federal prison.

In just a short amount of time, Jessica went from a local celebrity to unemployed and broke. There were days she couldn’t afford the power bill. Ramen noodle packets became a staple in her kitchen. The fancy jewelry she wore when she was living a lavish lifestyle was sold to strangers so she could have gas money to drive her daughters to school.

But what made life even harder was that Jessica found herself on the other side of the camera, as local media crews hounded her and her now ex-husband, Samir Cabrera, after he was charged with fraud for flipping real estate properties at inflated prices.

Over the years, Jessica has been praised in the local media and by people all over Southwest Florida, but she’s been terribly humiliated

and ridiculed by them, too. Her marriage crumbled. Her reputation was bruised. She lost her house, her job and her pride.

But today things are better. Much better.

That’s why she is here, ready now to share her story publicly for the first time. She wants people to know that she is OK and is eternally grateful to the countless many who supported her when she felt so horribly alone.

Those days are ones she’d rather forget, but she realizes she wouldn’t be where she is now without them.

“The one quote I repeated in my head 100 times a day is, ‘If you’re going through hell, keep going,’” Jessica says. “If you stop when you’re in the middle of your hell, you get stuck; you never get out of it. There were days when I wanted to just stop trying, but that quote would pop into my head. God has given me three amazing girls, and I wasn’t going to let our screw-ups be their problem. We were all going to get through it … and we did.”


She sits at a table outside a local Starbucks one weekday morning fumbling with her cell phone, dressed in a nice business suit and wearing just enough makeup to see she’s pretty enough without it.

She wants to pick a table away from the crowd, and once she sits down and wraps her jacket over a chair, she begins to talk about how nervous she is. She chooses her words wisely and does not say an ill word about her ex-husband because, when it’s all said and done, he is still the father of her three daughters—a set of twins, age seven, and a five-year-old—all who love their daddy as dearly as any little girl would.

When she begins to talk, you realize who she is. Even after all these years, people still recognize the blondish-brown-haired gal with the slender figure who looks you straight in the eye when she speaks. They remember the sound of her voice and the way she makes you feel as if you’re catching up with an old friend. On-camera or off-camera, Jessica was, and still is, the same likeable person.

But if you tell her that, she’ll blush or shrug it off. She’s not one for compliments and is modest to a fault. What she doesn’t mind bragging about is that people who knew her from the news still recognize her even though she’s been off the air for four years.

“I still have complete strangers come up to me and ask how I am. They are genuinely curious and concerned and are happy to hear I have moved on from those dark days to a much better place,” she says. “It does surprise me that strangers are still saying nice things to me. It’s a good feeling to know people still remember me fondly.”

Jessica had always wanted to be a broadcast journalist.

Her fifth grade teacher scribbled the suggestion on a graded paper one day and the idea quickly became her career goal. Growing up in Oregon, she was obsessed with female journalists such as Jane Pauley, and journalism quickly became a passion, even at age 10.

After studying journalism and political science at the University of Southern California, Jessica headed to Southwest Florida in a beat-up Jetta covered in Grateful Dead stickers. She migrated here because this is where her father, Don Stilwell, former Lee County manager, was and still is living. She waited tables for a while and eventually landed a news gig with Continental Cablevision. The hours were long and the pay was bad, but it helped her get a job with ABC-7, where she started off as a reporter for the 11 p.m. news. She stepped into the weekend anchor job with its sister station, NBC-2, a year later. In the years to follow, Jessica served as an anchor for every news broadcast on NBC-2.

“What she lacked in experience anchoring (at first) came through on the camera as someone who was genuine,” says NBC-2 anchor Kellie Burns, who has been close friends with Jessica for 15 years. “There are people who have been doing it for 20 years, and they put on an act when they get on the set, but Jessica is herself on the air. I really don’t think she has any idea of the charisma that she has, that she has something special.”

Other people have noticed that “something special,” too, including Samir Cabrera.

Jessica had just turned down a job in Cincinnati as a weekend anchor and decided to take her mind off it by going with friends to a bar in downtown Fort Myers. It was such a gross place, she says, laughing, and she remembers hating it as soon as she walked in.

Samir worked at the bar, and his job was to keep the crowd happy. He talked to her that night, and, as the weeks passed, they seemed to run into each other more and more. Finally, Jessica accepted his invitation for a sushi dinner.

Samir was extremely charming and smart. She liked the fact he had overcome many obstacles in his life. He came from Colombia at 11 and couldn’t speak English. He went to a school for at-risk children in Georgia, and then he moved on to college at The Citadel in South Carolina, where he graduated with a degree in business. Before Jessica met him, he had been in insurance, but wasn’t happy. He was working at the bar while trying to figure out his next move.

That move included wooing Jessica.

She wasn’t looking for love at the time. But, as with any unexpected romance, it just sort of happened. A year and a half after they started dating, he proposed to her on the air, something Jessica had asked him never to do. (Her face still blushes when she talks about it.) Within six months, she was walking down the aisle in a lavish ceremony in her father’s backyard, eager to say, ‘I do.’

She was 29 years old. Samir was 26. That was in 2003.

Jessica didn’t get a honeymoon because it was sweeps month at the news station. So the newlyweds quickly began their life together. She was a popular anchorwoman whose career was taking off. He was eager to get into real estate because business was booming.

They were talking about starting a family, and their life together, for a while, was good.

But life was about to spiral out of control, and there was nothing Jessica could do to stop it.


Their time together: Although her life appeared outwardly happy—with the perfect family, job and finances—the reality was far from joyful. “Money doesn’t take the place of happiness. I remember thinking, ‘Is this as good as it gets?’ ” —Jessica StilwellA year after they married, Jessica found herself not only with a flourishing career but a glamorous lifestyle as well.

Samir had found his calling in real estate. He dove in, eager to take advantage of the hot Southwest Florida market.

He started working for Frank D’Alessandro, who was the real estate mogul of Southwest Florida at the time. The deals Samir sealed allowed the young couple to afford things like a million-dollar house, a Porsche, a Rolex and a five-carat ring. They were so well off that they didn’t have to worry if there was enough money to pay their bills each month. (The monthly power bill for the house was $800.) Jessica could’ve quit working, but she didn’t want to because she loved her job.

Samir liked to spend the money he made. If you were out with him during that time, you knew you weren’t going to pay for a thing. He always had it covered. But Jessica stayed grounded. Yes, she had nice jewelry, clothes and furnishings, but she enjoyed the money in different ways. She donated to charities, bought nice presents for friends and family, and helped others when she could.

“I am who I am whether I have a lot or a little. I’m not pretentious,” she says. “We were not stingy with our money. We all enjoyed the time.”

Looking back, she says that though the money was nice, she would’ve traded it all for a stable family life.

“I would a million times take that over a family who had a lot of money but wasn’t happy,” she says. “Money doesn’t take the place of happiness. I remember thinking, ‘Is this as good as it gets?’”

During this time, Jessica was struggling to get pregnant. While her career was so very important, having a family was really all she ever wanted. Getting pregnant became a mission, and she even allowed viewers to peek into her private life as news cameras documented the journey she took of becoming pregnant through in vitro fertilization. Finally, in May 2005, she had her beautiful babies—twins Sophia and Olivia.

Eleven months later, she was pregnant again, but this time it was a huge surprise. She didn’t need doctors to intervene. It happened naturally, and Jessica welcomed the miracle. Arianna was born in December 2006. In a short amount of time, the woman who once thought she may never have children now had the pleasure of loving three precious girls.

A part of her life seemed complete, but Jessica realized another part was empty.

Her marriage to Samir was falling apart.

Jessica doesn’t like to admit defeat. But when it came to her ex-husband, she felt awfully let down. She admits she and Samir were struggling with their marriage soon after they took their vows. She won’t share the details, but, by the time the twins were born, it was clear to her the marriage was over. The thought alone ripped at her heart. Her parents divorced when she was younger, and she had promised herself that if she were to marry one day, she would never get a divorce. She knew how tough it would be on the children.

But she felt their marriage wasn’t a healthy one and, sadly, didn’t believe it ever would be. She knew divorcing would be one of the worst experiences of her life, but as she mentally prepared to go down the road to becoming a single, working mother, the FBI came calling.

And life for Jessica suddenly got worse.


When the real estate market crashed, projects started dying, and Jessica and Samir were hit hard. Money stopped coming in. They had no choice but to sell their jewelry, the cars, anything and everything worth something so they could pay the bills in a huge house they knew they couldn’t afford. With dwindling assets and what Jessica believed was an unhappy marriage, she figured they had hit rock bottom until Samir received a phone call from the FBI. He couldn’t afford an attorney at the time and figured he would talk to them on his own. He didn’t feel he had done anything wrong.

“I was terrified. It was horrible. I was trying to figure out what was going on,” Jessica says.

Samir had found himself tangled in a web of questionable real estate deals where lots of money had been lost and investors were angry. He had been working for D’Alessandro, who drowned during a kayaking trip in New Jersey in 2007. At the time, D’Alessandro was facing dozens of lawsuits from people who didn’t see the returns they were promised on investments they had made.

Now investigators wanted to talk to Samir.

Jessica made the station aware of the situation and found herself acting as a source for them. She was happy to help clear things up because she didn’t believe Samir would be charged.

But he was.

In June of 2008, he was arrested and charged with fraud involving commercial land deals in Fort Myers. The indictment alleged he flipped the properties, pocketed the profit and didn’t disclose to investors that he controlled both the company that sold the properties and the company that bought them.

The indictment came on the same day the couple was forced to leave their house because they could no longer afford the payments. At the courthouse, Jessica sat on one side of the courtroom, while her media friends sat on the other. Samir was in shackles and an orange jumpsuit. Jessica was mortified.

In the following months, her picture and name were splashed across newspapers and television screens as she escorted her then-husband hand-in-hand to and from the courthouse. Instead of being the reporter shouting questions, she was the one being shouted at. Even worse were the cruel things people were saying.

She couldn’t help but read the comments at the end of local news stories online and was astounded that complete strangers said the things they did. They called her a criminal, a scammer and said derogatory things that Jessica took to heart. Some were even almost silly, pointing out she didn’t bother to wear makeup or get her hair done for the trial.

“For so long there was so much stuff that wasn’t true and you had no control over it,” she says. “All I saw was the negative.”

Not long after Samir was indicted, Jessica learned her contract at the station wasn’t being renewed. When Jessica tells this part of the story, she covers her face with her hands and begins to cry. She loved what she did. Her career was part of who she was. And suddenly, it was gone.

“I didn’t even empty my desk,” she says, wiping tears from her eyes. “I understood the reason why, but it still hurt me. I felt deserted. It was like another thing that was destroyed, and it was gone because of Samir.”

Through the trial, Jessica struggled to stay upbeat for her daughters, but, in the end, they were the reason why she made it through each day.

“I’d cry and they’d say, ‘Mommy, why are you sad?’” she recalls. She tried her best to hide what was happening. They were so young at the time, they wouldn’t have understood even if she tried to explain it to them.

Many have wondered why Jessica stood by her man. She could’ve divorced him and easily walked away. Here’s what she says about this:

“Samir’s case was played out in the media. His lifestyle, the parties, the cars, the money … that’s what everyone saw. But the case wasn’t about all of that. It was very specific. There were 10,000 pages of discovery, and I read them all—not to mention I lived it.

“At this stage, I don’t think there’s a point in my trying to explain why I stood by Samir. First, I no longer have to defend Samir. And second, the only people I truly need to understand why I did what I did are my girls. And when they are old enough to understand what we were dealing with, I will explain to them what happened.”

In January of 2009, Samir was convicted of honest services fraud, a vague federal statute that at the time meant the jury felt Samir breached his fiduciary duty to his investors. He was sentenced to 10 years in federal prison and scheduled to leave that October. Jessica’s father was by her side that day, sitting in the court room and holding her hand. He remembers hearing her gasp. She remembers just feeling hollow inside.

Her girls were going to be without their father for a very long time.

“She was barely able to walk,” Don Stilwell recalls. “It was terrible.”

Samir lived with Jessica and the girls until his prison term started in the fall. That summer, Jessica stayed in seclusion, embarrassed and sad, afraid to be seen for fear of what people would say.

When it came time for Samir to leave, they told the children that daddy was going to time out.

Suddenly Jessica was faced with supporting her family on a small income she made while working for a property management company, where she only got paid if she rented a unit. Paychecks were random, and Jessica was stressed. Despite money being scarce, she still planned to make the trek to Pensacola every few weeks so the girls could see their father in prison.

She wasn’t sure how her family was going to survive the coming weeks, let alone the years to come. But, fortunately, for Jessica, there was a light at the end of her dark, ugly tunnel.


When samir left for prison, friends starting visiting again, and they realized Jessica was struggling financially.

Former co-worker and NBC-2 morning anchor Heather Turco collected money and letters from people in the community wishing her well. To this day, Jessica tears up when she talks about Heather’s kindness and the willingness of strangers to help her family stay afloat.

A family at her daughters’ school gave her $500 in gift cards to pay for gas and the girls’ Christmas gifts that year. Another local family paid the tuition at her daughters’ pre-school.

“I feel so blessed,” Jessica says. “Viewers saw me struggle to get pregnant and then deliver twins. They then went through my second pregnancy with Arianna, and I think they felt close to me. And I’ve seen that ever since.”

In January 2010, a friend introduced her to Joe Catti, founder of FineMark National Bank and Trust in Fort Myers. Joe, who enjoys giving back to the community personally and professionally, asked her about her situation and wanted to know what she needed.

“I was humiliated to tell him how bad it had gotten. I had always been able to support myself. But I sucked it up and gave him a brief explanation of what was happening in my life. Without hesitation, Joe asked if I wanted to work part time at the bank,” she says.

Jessica accepted.

That position was a temporary one, allowing her to make some money to help her get back on her feet. But Joe noticed Jessica was a savvy businesswoman and a hard worker. He was impressed with her and wanted her to stay.

Now she is working full time as the bank’s marketing director.

That was the beginning of a new life for Jessica, and to this day, she credits Joe for the change.

“I asked her if she had been involved in anything that was not legal, and she said absolutely not. I didn’t have a reason not to believe her,” Joe says. “Part of our culture is to always do what’s right. She is incredibly insightful and a very quick study with a strong work ethic. Once I got to know her, I wasn’t surprised.”

As things started to improve for Jessica, she got the news that, after one year away, Samir was being released from prison. The U.S. Supreme Court had limited the focus of honest services fraud during an appeal by disgraced Enron executive Jeffrey Skilling. The scope of the law no longer included the things of which Samir had been convicted.

That’s when Jessica made the decision to file for divorce. It’s a move she struggles with to this day.

“I knew I couldn’t go back to the way it was before he left,” she says. “My life was moving in such a positive direction. I couldn’t sacrifice that to take care of Samir. So I had to make the extremely difficult decision to tell Samir he couldn’t live with us. That was probably the hardest thing I’ve had to do. And while it hurt everyone at the time, I knew I made the right decision. I know I did what I had to do.”


Helping hand: FineMark National Bank founder Joe Catti gave Jessica a chance when few would. And it changed her life. “(I had) to tell Samir he couldn’t live with us. That was probably the hardest thing I’ve had to do.” —Jessica StilwellSharing her story is like ripping off a bandage covering a wound that hasn’t healed yet. Those bad years feel like one long, dreadful day to Jessica. They are memories she doesn’t care to talk about too often.

But what she does like to talk about is her life today.

Now she is living in a modest, two-story house in Fort Myers. Her girls are happy there, and so is she. There are times when she can’t believe that she owns her own place when not long ago she was begging Florida Power & Light not to shut her power off.

She spends time with her family and close friends when she can, and she’s even dating someone. The banking business, though it wasn’t what she dreamed of as a child, is a wonderful world for her. She’s proud to be a part of it. It’s allowed her to re-establish herself in the community.

She misses being on television and has had the opportunity to return to NBC-2. But when the station management came calling, she politely turned them down. She’s content where she is.

Samir lives in Miami, and he sees the girls every other weekend. He and Jessica have a better relationship now that they are no longer married. Samir, Jessica says, is a much better father. “It’s a surreal ending to a surreal experience,” Jessica says. “It’s second chances, I guess, and I hope he makes the best of it.”

She is no longer fearful of being judged in public. She sleeps well at night knowing her biggest challenge in the morning will be getting the kids out of the house on time, not figuring out how to pay the bills.

And now, when people approach her and want to know how she’s doing, she welcomes it.

“They say, ‘Oh, you look so happy,’” she says.

And most of the time she simply smiles and says, “Thank you.”

They’re right. Jessica Stilwell is happy.

And she plans to stay that way for a very long time.

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