(CMR) The mental health status of reigning Miss Cayman, Tiffany Conolly, played a critical role in her apparent defense of assaulting multiple people including striking a police officer in the face at the Detention Center.
Conolly appeared in court to answer to six charges, including common assault, property damage, and assaulting a police officer. She pleaded not guilty to all charges.
Her attorney put questions to the first key witness implying that Conolly was also denying a large portion of the assault against a 58-year-old man who was viciously assaulted at his own front door. The man explained how he had forbidden Conolly from coming to his house several weeks prior to October 15, 2021.
The trial of Conolly got underway in Summary Court before Magistrate Philippa McFarlane. The prosecution called three witnesses, including the father who was assaulted as well as two police officers that attended the scene.
The father noted that he was at home watching TV when he heard “an extremely loud banging” at the door around 10:00 pm. He had expected it to be Conolly because she messaged his son to say that she was on her way over there. The two had been in a relationship for about three months before it ended.
He noted that his son was given strict instructions that because she had previously had an incident at their residence involving a mobile phone, she was not allowed to return there.
Being concerned that Conolly was going to break the glass in the door, he opened the door to find a “belligerent, hostile and threatening” Conolly shouting for his son to come out. The father then immediately asked her to leave as she attempted to push her way past him to get into the house. He testified that unable to get past him, she took a step back and struck him in the face.

That assault knocked off his reading glasses to the ground before Conolly picked them up. He gave a detailed account of him pleading to get his glasses back, only to have the beauty queen look him directly in the eyes, hold the glasses up in his face with both hands before “bending and crumbling them” and then threw them on the ground.
“She look me dead straight in the eyes and with both eyes bend and crumble them and threw them to the ground. She held the glasses up and destroyed them”.
As he stepped forward to retrieve the glasses, Conolly then punched him in the head. He said he was taken aback and immediately called 911 for help. As the assault continued, he called for help from a neighbor and his son eventually came downstairs to assist him.
The front doorstep attack resulted in him being repeatedly assaulted with his lip being popped, headbutted, scratched and clothing ripped. The son also sustained a bite on his chest, headbutted and scratched.
On cross-examination, Oliver Grimwood put a different version of events to the witnesses, which he denied and called a “complete fabrication” and “absolutely false”. Grimwood pressed the witness that he had pushed Conolly down on the steps and had assaulted her on the night in question.
She went on to throw her bicycle on one of two family vehicles and threw a brick on the windshield of another vehicle. At some point, her mother arrived at the scene before the police. He testified that Conolly said to her calm mother:
“Mommy, why do they always do this to me”
At this stage, the witness became very emotional on the stand and began crying. Police officers both testified that during the journey to the Detention Center, she was kicking something inside the vehicle. She went on to become disorderly at the lockup, including assaulting the officer and refusing to remove jewelry.
Her defense attorney played heavily on the fact that Conolly has had a history of mental health issues and pressed the police for why she was not treated as such. The court heard that her physician signed off on her mental fitness for the police interview.
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The trial continues on December 5 and 6, when the defense makes its case. Two days have been set aside for the continuation of the trial.
The Miss Universe Pageant International Pageant will be held on January 14, 2023, in New Orleans, Louisiana. It remains unclear if she will be in attendance as the Miss Universe Cayman Committee has indicated they would be making no decisions before the outcome of the pageant.
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