Woman Pregnant 13 Times In 10 Years To Avoid Jail Sentence


Back Into A Corner 

“It’s not looking good,” her lawyer whispered under his breath as he tried to maintain a nonchalant pose. The judge was talking before them, reading all the charges she was facing. 

Her mind went blank as she heard her sentence. Her eyes grew wet, and her mind started working out ways to keep her out of the jail term.

Her solution would leave everyone speechless. 

One Last Witness 


But for Massachusetts native Amanda Rosenbaum, things weren’t supposed to go this way. She was sure she’d beat the case.

Her lawyer had been working overtime to prove her innocence. 

They were on their way to winning the case when the prosecutor called in their final witness. One look at him, and Amanda knew all was lost. 

What Happened?


What started as a needed way to pay off an infraction had quickly devolved into this. Amanda had gone in too deep; before she knew it, she was standing in court. 

But where did it all begin, and why would she resort to such drastic measures in a bid to escape jail time?

Was she innocent of everything the court was convicting her for?



Amanda was born in a well-to-do part of Princetown, Massachusetts.

Her childhood had started as the best before everything quickly devolved into chaos. 

She lost her dad at the tender age of six. Her mom remarried almost immediately, throwing her and her little brother into an endless nightmare that would define her life as an adult. 

A Sad Household 


Amanda’s stepdad had been stern since the first day she met him. But as the months passed, it became clear that he didn’t have Amanda and her little brother’s best interest at heart.

He wasn’t a good dad and always took things too far. It didn’t help that her mom developed a substance abuse problem during this time.

Before the two kids knew it, they were in foster care, hoping for a better family to find them.

At The Foster Home 


But for Amanda, it seemed life would never let up. Her brother found a loving family who took him in and treated him like a prince.

Meanwhile, Amanda was left in the foster home by herself. The environment wasn’t the best, and it wasn’t long before she found herself running from the law.

If she had been smart, she would have changed her ways then. 

Fear Builds Character 


Amanda had already been to court twice by the time she turned eighteen. She knew that she would be tried as an adult if she ever got in trouble again. 

That meant jail time, a frightening reality she wanted to avoid at all costs. That fear made her focus on school. It got her a GED certificate, enough to step into the adult world and look for a job.

But an old dog cannot learn new tricks. 

The Easy Way Out 


Amanda managed to land a job at a local deli as a salesperson. She plowed the little cash she had into buying a business degree.

Yes, she didn’t spend even a second in any college in the country. She only took a quick way out. 

She’d forgotten her old life where she was a sweet little girl with a little brother who looked up to her. Out here, she was all alone. She’d do anything to survive. 

Lie And Cheat


Amanda had always been an ambitious person. Additionally, she was constantly starved of the good things in the world and craved to have everything. 

She’d heard how great her brother had it and wanted to live to those standards.

To her, the only way she’d do that would be to lie and cheat her way through life. 

Fifteen Years Down 


Fast forward fifteen years, and she was the head chief financial officer of one of Massachusetts’s most prominent non-governmental bodies. 

Of course, her climb to such a prestigious position was shrouded in darkness and mystery, with anyone who would dare speak against her suffering her full wrath.

She thought she was unstoppable until everything came back to bite her. 

Where She Began 


Amanda’s devious activities started with embezzling the company funds. As the head of the financial department, she was in charge of all company spending and profits. 

The first time she stole cash from the company, she’d been in dire need. She’d just bought a new flashy car and had not finalized its insurance.

Regardless, she decided to take it out for a quick drive. She’d be unconscious by the time she exited her driveway. 

Right Through!


Unaware of the vehicle’s true power, Amanda stepped on the gas and shot through her driveway and into her compound’s concrete wall.

She hit her head and passed out, but her foot was still on the gas. 

The vehicle roared as it poured through the rubble of bricks and concrete, t-boning an SUV lumbering down the road. This crash would change Amanda’s life forever. 

Paying Up 


After buying the car, Amanda was strapped for cash. She decided to skim a little off the top at her company to cover the damages caused by the accident. 

The man whose SUV she’d driven into didn’t take her to court. Of course, Amanda had greased his hands with a hefty sum for him not to take any action.

She was confident stealing from the company would be a one-time thing. It wouldn’t. 

Forming A Habit


Amanda started taking small amounts from the company. She’d make sure to cook the books so everything would seem fine to her superiors. But her appetite grew with every cent she took. 

She’d started with a few hundred dollars – peanuts to someone in her position.

She would use this cash to pay for expensive lunches and dinners with her friends. But this would soon change. 

Only The Beginning 


The few hundred turned into thousands. Amanda was getting bolder. She went as far as cutting down the employees’ salaries while telling her bosses she didn’t.

They had no idea she was taking huge percentages of people’s salaries every month.

She didn’t care that she was ruining people’s lives. But she was only getting started. 

Going Big


Stealing from the company wasn’t enough. Amanda made dangerous friends in unsavory parts of the state, some of them working in government and others owning large companies. 

Together, they formed a corruption ring, stealing as much as they wanted. They bribed and threatened their way through the state.

By the time the state caught wind of what they were doing, it would be too late. 

How Did She Get Caught


Amanda stood in the courtroom, still trying to wrap her head around how she got caught. It had been a stupid mistake on her part. 

She’d accidentally sent the wrong payroll to the company accountant, showing the actual amount of cash everyone in the company was supposed to get.

She was supposed to send the one she’d cooked. Her life as she knew it was over. 

Damage Control


Amanda tried to do damage control. She sent email after email informing the accountant that the payroll she’d sent was a different one that she and the board had been discussing a few months ago. 

She even drove to his house that night, trying to get a hold of him. But she couldn’t find him.

The following day, she got a call from her boss. 

Panel After Panel


The aftermath was a nightmare for Amanda. She stood before panel after panel, explaining why hundreds of thousands of company dollars were missing. 

She had to explain why she’d cut employee salaries without consulting her boss or the board.

What had she done with the millions of dollars supposed to go to her fellow employees?

Her Dirty Laundry 


Amanda’s story took to the airwaves, and soon enough, an inquiry was sent to every business, company, and government sector she had done business with.

This exposed all her dirty laundry, from corruption and bribery to darker activities that would ensure she spent the rest of her life at a maximum security prison.

But Amanda wouldn’t go down without a fight. 

You’re On Your Own


The first thing she did was try to contact her friends in powerful places. Connections run the world, and Amanda had enough. 

But each contact she called went cold. No one would pick up her calls, fearing she’d smear mud on their immaculate reputations.

Just as she was when her little brother left her at the foster home, Amanda was all alone again. 

Bringing In The Professionals 


She spent a hefty amount of money on lawyers, finding the best money could buy. The lawyers did everything in their power to keep her from getting sentenced. 

They requested that court dates be postponed and bullied the jury into canceling their attendance. They did their best to get the case dismissed.

But it would only be a matter of time before they ran out of tactics. 

She Got This!


The state was eager to see Amanda brought to justice. It brought in its own top-of-the-line lawyers and a judge who didn’t respond to fear or favor. 

Before Amanda knew it, she was standing before the judge, her heart beating as she watched her lawyers plead her case.

She knew she was guilty but hoped she’d walk away a free woman.

We’re Winning! 


The case, which had gone on for months now, was almost coming to an end. Amanda’s lawyers assured her she would win. 

They even set up a party back home, knowing this was their final court date. Amanda, who was facing life imprisonment, couldn’t be happier.

But that was before she saw the last witness. 

Payroll Guy Returns


It was the man she’d sent the wrong payroll to, and he had extensive evidence that she’d committed all the crimes she was being accused of. 

Among the documents he had with him were cash transfers Amanda had authorized, each funneling company funds to her private bank accounts.

He had phone recordings of her with her dangerous friends making plans to drain the state of its cash. Amanda didn’t even know the tapes existed. But that wasn’t all.  

Caught On Camera 


The man had video recordings of Amanda taking part in shady dealings all over town. The mood shifted in the court, and Amanda knew it was over. 

“It’s not looking good,” one of her lawyers whispered under his breath as he tried to maintain a nonchalant pose.

The judge was talking before them, reading all the charges she was facing. 

I’m Pregnant


Due to the staggering amount of evidence presented at the court, Amanda was sentenced to life imprisonment for graft, among other charges. 

But in a state of panic, she screamed out, “I’m pregnant.” True enough, she was a month pregnant, a fact that even she had forgotten.

The court fell silent. It seemed she wouldn’t be going to jail today. 

The Final Decision 


The judge looked at Amanda closely before calling for a pregnancy test. A week later, everyone convened at the court once more.

Since Amanda was pregnant, the court made the probation decision.

Amanda was ordered to follow certain conditions set forth by the court under the supervision of a probation officer. She’d go straight to jail if she broke any of these rules. 

Returning To Form


The court expected her to carry forward with her pregnancy term. But as soon as Amanda stepped out of the courtroom, she scheduled an abortion. 

She didn’t tell anyone what she’d done apart from her lawyers, and for the next eight months, the court knew she was pregnant.

They had no idea the extent she was willing to go to escape going to jail. 

A Miracle


Amanda did everything from wearing a fake belly to having a fake delivery date set by doctors she’d paid off. But she claimed she’d lost the child a few weeks before delivery. 

Of course, the court gave her a mourning period, telling her the case she thought she beat was still pending. But to their surprise, Amanda came out of the morning with another positive pregnancy test. “It’s a miracle,” she smiled while talking to the local press. 

Disclaimer: To protect the privacy of those depicted, some names, locations, and identifying characteristics have been changed and are products of the author’s imagination. Any resemblances to actual events, places, or persons, living or dead, are entirely coincidental.