Jake o'Brien by Josh Hodges

An early arrest for stealing boats and taking them for a joyride at age 12 led Jake O’Brien, now 23, to a young life that wove in and out of the Florida prison system.

Jake as a child.

It all began long before that. From the time he was a young boy growing up in Port St. Lucie, O’Brien said, he got involved with the wrong crowd, many of them older than himself. That early association set him on the path to petty crime that would consume him as a teenager.

A young Jake O'Brien.

Whether it be burglary, drugs or stealing boats for fun, O’Brien said he tried a little bit of everything.

However, it wasn’t until he was 12 that O’Brien came to the attention of law enforcement. From then on he was in and out of jail and prison and off and on probation for a number of different charges.

He finally ended up spending six years in a juvenile program for everything from trespassing to assault with a deadly weapon and tampering with a witness. O’Brien didn’t get outside the walls of a correctional facility until he was 18.

O'Brien having a video chat while imprisoned.

Trouble for O’Brien didn’t end there.

No more than a year later at the age of 19, O’Brien faced even more trouble.

Over the next four years O’Brien spent five separate stints in jails and prisons throughout Florida for a handful of crimes. These offenses ranged from violating probation to leading the police on a chase that finally ended with him being found by K9s and helicopters.

He most recently got out in October 2016.

Life Outside of the System

The realization of what life is like outside of a cell drove O’Brien toward rehabilitation.

“The importance of life and freedom and the opportunities available to me in the free world is what changed my life and lead me away from a life of crime,” O’Brien said.

O'Brien now.

Although he’s still relishing the freedom of a life without crime, O’Brien said he plans to go back into the Florida justice system, this time not as an inmate, but as a force for good.

“I plan on going back into systems and try to make a difference and lead people into a better life and away from the system,” O’Brien said. “I’m interested in getting involved and everything there is to do to make a change and change people’s mindset on life in general.”

Since his release last October, O’Brien has begun counseling a close friend of his.

In recalling a conversation he had with a counselor when he was 16 and imprisoned in the Okeechobee County Juvenile Division, O’Brien also hopes to send the message that a person’s life doesn’t end once incarcerated.

“[By] being the best that you can at one thing and not being distracted by all this other stuff. You know, master something and be the best at it,” said O’Brien, who now lives in downtown Vero Beach.

For O’Brien, that “one thing” while in prison was fitness and his art: tattooing.

“Every time I’d go in, I’m drawing and working out,” O’Brien said. “I used it to my advantage. I didn’t go in there and just waste time and you know, get involved in stuff that I shouldn’t get involved in. I went in there and made my time better.”

If there is one good thing that came from his prison time, O’Brien said it was the lesson he learned there.

“The fact that you have freedom to do whatever you want and to live,” he said. “It goes for people that’ve been to prison, people that haven’t been to prison and people that may end up in prison.”

“You’ve got to respect your life and what you’re doing and respect the people around you and just, you know, not take advantage of that,” O’Brien said. “Just enjoy your life because it can be taken at any moment you know, through death or prison. In prison, that’s not life.”

Created By
Joshua Hodges


Courtesy of Jake O'Brien

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