Years before he was arrested for an alleged fight with a 14-year-old student, a Poinciana High School campus monitor resigned from the Orange County Corrections Department amid an investigation into an allegation that he engaged in “improper behavior” with an inmate, according to newly obtained documents.
John Carrasquillo, 62, was arrested earlier this month and faces a charge of child abuse without great bodily harm.
The Osceola County Sheriff’s Office said Carrasquillo “forcibly pushed” the student into a golf cart after a dispute over the student’s phone.
A spokesperson with the Osceola County School District told News 6 that Carrasquillo was hired in January 2025 and was not permitted back on campus “pending the completion of all investigations.”
“The School District of Osceola County has followed and continues to follow all requirements prescribed by Florida law and District policy,” spokesperson Dana Schafer said this month. “A review of this matter confirms that the employee was hired and cleared through all required procedures. The Superintendent intends to recommend the employee’s termination at a regularly scheduled School Board meeting, pursuant to applicable state law and subject to the provisions of the collective bargaining agreement.”
Shortly after we reported Carrasquillo’s arrest, News 6 received a tip from a viewer who claimed Carrasquillo was a former corrections officer.
Through a public records request, News 6 was able to confirm that Carrasquillo did indeed work as a corrections officer at the Orange County Jail from 2007-2013.
123 pages of employment records detail Carrasquillo’s tenure with the Orange County Corrections Department, which featured discipline for an arrest related to alleged stalking.
2007
Carrasquillo was hired by the Orange County Corrections Department in 2007. His personnel file details his employment history, which included time as a corrections officer in New York City.
Months later, in December 2007, Carrasquillo is compelled to resign because he did not pass his certification examination—twice.
“I would like to thank you for giving me the opportunity to join your team with the Orange County Correction Department,” Carrasquillo wrote in his resignation letter. “I hope to return soon.”
2008
Just a month later, in January 2008, Carrasquillo did return to the department.
In July of that year, a supervisor left the following note in Carrasquillo’s file:
“Counseled Ofc. Carrasquillo in regards to an incident that occurred in his dorm 7/10/08. Informed him that shakedowns were not [to] be used as a form of punishment and to contact a supervisor before one is conducted.”
The supervisor wrote that Carrasquillo was “receptive to counseling” and stated the incident would not happen again.
An evaluation of Carrasquillo later that year concluded that he was “an excellent team player” who “accepts responsibility for his actions.”
“Officer Carrasquillo is an asset to the Orange County Corrections Department,” the evaluation reads.
2009
Carrasquillo’s personnel file includes documents from the Osceola County Clerk of Court, detailing court appearances Carrasquillo had to make for a stalking arrest.
Days after he was granted pretrial release for the first-degree misdemeanor charge, Carrasquillo received a memorandum from a work supervisor.
The supervisor cited one of the conditions of release: Carrasquillo could not possess a gun.
“As you know, being able to carry a firearm is an essential function of a Correctional Officer position,” the supervisor wrote, explaining that the pretrial release conditions rendered Carrasquillo unable to perform his assigned duties. “For that reason, as of September 29, 2009, you will be assigned to work in a no-contact inmate position.”
A week later, Carrasquillo’s supervisor returned him to normal duty after a judge authorized Carrasquillo to “possess a firearm only while working.”
News 6 checked the Osceola County Clerk of Court website and the case number mentioned in the personnel file did not produce results.
2010
In April 2010, a supervisor sent Carrasquillo a memorandum outlining the results of an internal affairs investigation born out of Carrasquillo’s arrest.
“You were charged with Stalking as a result of repeated anonymous calls made to your wife’s friend,” the memorandum read.
The memorandum ended by notifying Carrasquillo he was suspended for three days without pay.
That same year, the Orange County Sheriff’s Office investigated Carrasquillo for sexual battery.
The Sheriff’s Office confirmed the existence of that investigation for News 6 but said it did not proceed forward because the victim did not wish to seek prosecution.
2013
On Oct. 2, 2013, a supervisor sent Carrasquillo a memorandum re-assigning him to a different part of the jail where he would have no inmate contact “until further notice.”
“The purpose of this memorandum is to officially advise you that I received an allegation that you may have been involved in an improper behavior with an inmate while on duty,” the supervisor wrote.
The details of the alleged improper behavior were not included in the memorandum.
Later that month, Carrasquillo issued a letter announcing his resignation “due to personal reasons.”
2015
News 6 also reviewed information from the state’s Criminal Justice Standards & Training Commission, which revoked Carrasquillo’s correctional license in August 2015.
A category entitled “Offense” lists sexual battery, indecent exposure, and misuse of public position.
It’s not clear if that license revocation was tied to any investigation by law enforcement or the corrections department.
TODAY
In an e-mail attaching Carrasquillo’s personnel file from his time as a corrections officer, News 6 reached out to the Osceola County School District again Wednesday to ask about his past.
The district’s spokesperson sent along the same statement we received earlier this month:
“The School District of Osceola County has followed and continues to follow all requirements prescribed by Florida law and District policy. A review of this matter confirms that the employee was hired and cleared through all required procedures. The Superintendent intends to recommend the employee’s termination at a regularly scheduled School Board meeting, pursuant to applicable state law and subject to the provisions of the collective bargaining agreement.”