Gainesville Man Faces 20 to Life for Alleged Jewerly Robbery
Editor’s Notes: The police reports and court documentation have been edited slightly for smoother readability.
As of May 12, 2026, Randy Harry Simmons Jr., 22, has been in the Alachua County Jail for one year. He currently awaits trial and faces 20 years to life in prison on felony charges of robbery with a firearm, aggravated battery, and escape (attempted), along with a misdemeanor count of resisting an officer without violence.
Gainesville Police Department (GPD) officers arrested Simmons on May 12, 2025, and charged him with an additional count of using a firearm while under the influence; however, prosecutors are not proceeding with this charge.
Simmons has no local criminal history but he has a prior from outside of Florida dating back to 2023. It’s currently unclear what this is for because court records don’t indicate what state/county the incident is from.
Police Report 1
Detective Matthew Quinn reported the following:
At around 9:45 p.m., GPD law enforcement officers responded to Summit House Apartments in reference to a report of an armed robbery. Upon arrival, officers located the 66-year-old female victim with numerous injuries and covered in blood.
The victim later received over a dozen stitches to her right ear and the left side of her forehead. She had a broken left hand/wrist and a broken nose.
The victim stated that a Black male in a grey hoodie attacked her in the pool area of the complex by striking her numerous times with the butt of a pistol. The victim stated that during the attack, the suspect demanded she transfer money/cash to him. The victim stated the suspect grabbed her phone from her and attempted to send himself money but failed. The victim stated the suspect stole her white gold ring from her hand during the attack/robbery. The ring has three diamonds valued at $1,000.
While police were investigating this incident at the apartment complex, an informant called the Combined Communications Center to report that a Black male in a grey hoodie was hiding underneath a truck inside of the complex. Officers responded and located [Simmons] hiding underneath a pickup truck while armed with two pistols. [Simmons] was ordered to surrender to police detention, but he resisted by ignoring numerous commands to get on the ground.
Once detained, [Simmons] was transported to GPD. [Simmons] was found to have smeared blood on his left leg and blood on one of the guns found in his possession… All the blood is believed to be the victim’s due to [Simmons] not having any fresh bleeding wounds.
Officers were able to follow a blood trail from the victim’s apartment that led police to the pool area. Located in the pool area were numerous .45-caliber rounds of ammunition that matched the ammo found in [Simmons'] .45-caliber pistol.
Police soon contacted the witness who is [Simmons'] girlfriend. Post Miranda, the witness confirmed that she heard a commotion outside, exited her apartment, and observed the victim on the ground yelling ‘Ahhhhh’ while [Simmons] stood next to the victim.
Post Miranda, [Simmons] stated he has been drinking heavy amounts of alcohol tonight. He confirmed he was in possession of both of his firearms tonight upon his arrest. He confirmed that he was angry with his girlfriend tonight. He was standing in the pool area in the apartment complex when the victim started to record him. The victim did not tell him anything but was just recording him with her cell phone (in a public area) which upset [Simmons]. He does not remember attacking the victim but does agree he likely did. He agreed that the blood police found on his gun likely belongs to the victim. [Simmons] complained of an injury to his hand (likely due to him striking the victims numerous times with the pistol butt).
LEO could smell a strong odor of an alcoholic beverage coming from [Simmons]... He was identified via his Georgia driver’s license.
Police Report 2
Detective Quinn filed another police report regarding Simmons’ escape charge with states the following:
Around 1:20 a.m., I concluded my post Miranda interview with [Simmons] and informed him he is being charged with armed robbery and aggravated battery.
Around 1:39 a.m., [Simmons] was complaining about the handcuffs being too tight and said, ‘Can I get these cuffs off me?’ I told him that I saw no reason as to why I should take the handcuffs off of him. [Simmons] states, ‘I’m in an interrogation room bro, I’m not getting out of here.’ I did loosen the handcuffs in order to appease him as an empathetic act.
[Simmons] also confirmed that he understood he was under arrest by saying, ‘You are the only person who has told me what I’m getting arrested for.’ Before I left the room, [Simmons] asked, ‘Am I going to county jail tonight?’ and I responded, ‘yes sir.’
At 1:48 a.m., [Simmons] goes up to the room window for a moment, and then picks up my body cam which is recording him in the room. [Simmons] has the body cam in his hand for only 22 seconds before he puts it up to the scan pad on the wall and scans it in the exact same motion that he had watched me do (with my key card wallet) a couple times tonight in order to exit the room.
[Simmons] clearly wanted his handcuffs taken off just prior to this obvious attempt to try and escape custody/confinement. [Simmons] then proceeded to press buttons on the body cam for 60 seconds until he successfully turned it off.
I later returned to the room and noticed the body cam was turned off. I asked [Simmons] if he had turned it off and he confirmed he did. I asked [Simmons] why he turned it off and he stated it was because he did not like being recorded. [Simmons] deliberately failed to mention that he had thought the body cam may have had capabilities to unlock the door and had scanned it on the scan pad in an attempt to escape the room.
Criminal Case Proceedings
Simmons was not granted bond after his arrest, with prosecutors filing a successful pretrial detention motion.
On June 13, 2025 prosecutors filed formal charges against Simmons, along with a notice of intent to seek enhanced penalties against him as a 10/20/Life Offender.
On June 23, 2025, Criminal Defense Attorney John A. Ramsey began representing Simmons.
Towards the end of June, Simmons wrote a letter to the court that stated the following:
“Request of Plea
To whom this letter may concern,
My name is Randy Simmons. I am not admitting guilty nor not guilty to any charges within this letter. I ask that this letter isn’t used against me, but on my behalf for my case. I am not looking for sympathy within this letter, but any consideration for a fair second chance. A Second Chance I would forever be grateful for and not take for granted. I am not seeking a slap on the wrist, but only a fair plea deal without prison time.
I am fully aware that my charges are serious ones that deserve time in prison. Even though I solely believe that some of my charges I’m not guilty of, I am willing to take on [them] and the conviction if a plea deal that is seemed fit in my and the state’s behalf can be granted to me.
This is my first time on Felony Offenses. I have no history of violent acts for I am not a violent person. The night I received these charges, I was assaulted by my victim before I became the aggressor, and I was not in my right mind for I was heavily intoxicated. In the end, I’m fully aware that these are not excuses for I should not have taken matters as far as I did if I felt assaulted. I should have contacted authorities and not been as intoxicated as I was…
I have made a grave mistake that I shall never repeat. Please have consideration for my mistake doesn’t define me as a person as I am not the person my actions have displayed. I am not a violent person, criminal, robber… or gangbanger. When you look at me, the single tattoo on my face is in remembrance of my dead grandmother.
I do not envy jail or prison for this is not the life I want to live or be the person constantly in and out… Whether I believe I’m guilty or not to some of the charges filed against me, I am willing to put down my sword and shield and not fight this case if a reasonable plea deal can be granted to me. Reasons as to why I’m eagerly willing to do so is for one, I have heavy remorse and sorrows towards my victim. Regardless, any actions my victim took against me that led to our altercation, I know with a heavy heart that I was wrong with how I retaliated against my victim.
Another reason is that even if I believe I am guilty or not… or if there is sufficient evidence or not… There are actions I took that led me to this case such as being heavily intoxicated…
Within a plea deal, I ask that it be considered sentencing me to a drug/alcohol program for however long it is seemed fit…
In addition to a program, I am willing to take house arrest or probation for 8-16 years or however [it should] correspond with my charges and punishment without prison time. I will not fight my charges or go to trial if this deal or one similar can be granted to me. I beg and plead that a second chance is considered for me. For giving one to me will not be a mistake… I will not take it for granted, for I have, and will have learned my lesson and will show that I can and will be a citizen that abides by the law and normally functions within society.”
In June 2025, prosecutors disclosed their witness list to the defense, which includes many GPD officers.
In September 2025, Simmons wrote another letter to the court in which he raised concerns about Ramsey’s representation of him. In the letter, Simmons references a plea offer that he does not find favorable, but the specific contents of the deal are not clear. The letter states:
“Request for Representation
To whom this matter may concern,
My name is Randy H. Simmons. I am currently being held in the Alachua County Jail. In the midst of my case, I have had two different public defenders appointed to represent me (Canaan R. Goldman & David R. Ciantci). Upon feeling as if I needed better representation for my case, I hired John A. Ramsey… Since I have hired Ramsey, I feel that he has not been representing me to the best of his ability or has not put any effort into representing me in my case. Ramsey has not filed any motions, hearings, or depositions on my behalf. He has been breaking attorney client privilege with his wife. She has been lying to me regarding matters within my case in an attempt to scare me into signing the plea.
Ramsey has not been out to visit me to discuss matters or update me on my case… only one time. Within this one attorney visit, Ramsey’s wife stated to me, ‘When the judge is done sentencing you, you’re gonna wish you’ve taken the plea.' In addition to this statement, Ramsey’s wife has lied to me about evidence present within my case. These tactics and violation of my attorney client privilege has made me feel uncomfortable and that it is not in Ramsey’s interest to properly represent me in this case. Upon this feeling, I have told [my girlfriend] to not continue payments to Ramsey… As a result, Ramsey stated that me nor [my girlfriend] contact him and has sent me a motion to withdraw from this case.
As a result of these circumstances, I am requesting to be appointed regional conflict counsel for I have had a paid attorney and public defenders and feel they have failed at proper representation and I do not wish to represent myself in this case. If regional conflict counsel is not deemed to seem fit for this scenario I ask to be appointed any form of representation to correspond with my case…”
On October 6, 2025, Judge Robert Groeb granted Ramsey’s motion to withdraw. Soon after Cianci would resume his representation of Simmons.
On April 4, 2026, Simmons submitted a motion for a Nelson Inquiry regarding Cianci. Defendants can submit a Nelson Inquiry when they feel their attorney is not properly representing them. The motion states:
“Defendant Randy Simmons motions the court for a Nelson Inquiry where the law office of David R. Cianci (Florida Bar #94637) renders ineffective assistance. In Support thereof, the Defendant submits the following.
1. Defendant has given Counsel defense tactics that Defendant believes can possibly prove his innocence. Yet, counsel denies [them] stating, ‘If I place this defense in court I will lose my Florida Bar license.’ Counsel steadily denies any pretrial tactics brought forth and continuously attempts to convince Defendant to plead guilty to charges, stating, ‘Taking this plea is your best option if we go to trial you will lose and get the maximum sentence…’
2. Defendant believes Counsel has already predetermined the Defendant guilty of all charges due to certain wording during attorney client meetings such as, ‘You did,’ ‘when you did,’ and ‘it looks like you did it.’
3. Defendant feels as if Counsel and State Attorney have too much of a social connection as Counsel refers to and emails State Attorney Daniel Ley as ‘Danny’ and ‘Danny Boy.’
4. Counsel seems to side with the alleged victim due to Counsel comparing the Defendant’s and the alleged victim’s race, age, and sex to severity of alleged crimes.
5. These tactics used by Counsel are believed to be unethical and render ineffective assistance of counsel. Nelson V. State, 274.
Wherefore, The Defendant requests that the court appoint conflict-free counsel…”
It’s unclear how Judge Groeb responded to the motion for a Nelson Inquiry, but records show Cianci is still Simmons’ attorney as of his May 4, 2026 case management hearing.
Groeb’s upcoming retirement was recently announced, meaning Simmons will likely get a new judge if his case isn’t resolved soon.
Several depositions are scheduled to take place throughout June 2026. Simmons has a case management hearing set for June 8, 2026.
