Ex-Miss Cayman dodges jail in assault case

| 15/11/2023 | 34 Comments
Cayman News Service
Tiffany Conolly arriving at court (file photo)

(CNS): Tiffany LeAnn Conolly (25) from West Bay was handed a six-month jail sentence on Tuesday in relation to an assault at her ex-lover’s family home in West Bay more than two years ago. However, that jail time has been suspended for two years. The former pageant queen lost her Miss Cayman Islands title following a conviction for assaulting her ex-boyfriend, his father and a police officer.

Conolly was found guilty of common assault, damage to property, assaulting police and disorderly conduct in Summary Court back in February. But the sentencing hearing has been repeatedly delayed as a result of issues relating to mental health reports. However, on Tuesday morning Magistrate Philippa McFarlane handed down the suspended sentence.

Conolly was also ordered to pay $2,260 as compensation for damaging the cars of her ex-lover and his father as well as a pair of reading glasses. If she fails to pay the fine within one year, she will go to jail for three months, the court has ordered. She has also been directed to attend anger management classes, to seek mental health treatment and undergo routine drug tests.

During the trial last year, Conolly denied assaulting the two men and implied that her ex and his father had threatened her. She argued she was defending herself, a claim the magistrate did not believe. Conolly did, however, blame the incident on an episode of mental illness, which was supported by medical reports.

McFarlane also noted the failure of the courts to record previous convictions for Conolly for similar offences. It was because there was no criminal record that Connolly was allowed to continue to compete in the 2022 Miss Cayman pageant, which she went on to win, which placed the committee and the tourism ministry in an awkward situation that has led to government pulling out of the beauty contest business.

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Category: Courts, Crime

Comments (34)

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  1. Anonymous says:

    She doesn’t deserve to goto jail.
    Counselling is most appropriate.

  2. Anonymous says:

    Hopefully this time around she is receptive to the mental health treatment she requires. The court stated she has previously denied court orders of doing just that and missed appointments set for her. It is interesting that she is being routinely drug tested; is it a measure of ensuring she is taking the medication she is prescribed by her psychiatrist? Hopefully so. I think her mental illness is far greater than she is/this trial has let on, which is why she is being given yet another chance. Sending her to the prison here would probably do far more harm than good when really what she needs is to be in a mental facility receiving rehabilitative treatment; which as we all know Cayman lacks..

  3. Anonymous says:

    I suppose we have to be grateful she had no conviction recorded. Thats par for the course in Cayman Courts. Weak justice or no justice.

  4. Anonymous says:

    Like a furious jungle cat! Attacked BF, BF’s dad, car and police officer wow Tiffany intensity could fit well as a UFC cage fighter!

  5. Anonymous says:

    I was once charged with ‘insulting the modesty of a woman’ for saying she was incompetent, that is how stupid the law is!

  6. Anonymous says:

    Psycho. Lots of those around here

  7. Anonymous says:

    So have the pageant organisers ever stated what has happened with the prizes award at the contest? I sincerely hope that she has not benefitted financially and the scholarship funds will be used by the revised winner.

  8. Anonymous says:

    3, yes THREE counts of assault (police officer, guys dad and guy) and still suspended 😂

    Anyone know this birds background? What kind of Caymanian is she? New neighbour Caymanian or wah?

  9. JTB says:

    It’s hard to understand how a conviction for assaulting a police officer can not result in a custodial sentence.

  10. Anonymous says:

    Hopefully she gets her life back on track.

  11. Anonymous says:

    So you just keep committing crimes like the previous ones never happened? The prior decisions not to record a conviction should always have a caveat that future convictions rescind the waiver and you bare the full force and effect of the Law.

    • Anonymous says:

      Some may remember the Englishman, still here, who was caught 7 figures deep in the developers’ cash register, and he was incredibly charged with “Deception”.
      This slap on the wrist meant that he has continued to “deceive” many business partners, and always settles with NDAs.
      Slaps on the wrist are no deterrent to criminal minds.
      Punishment that hurts freedom, the pocket, or reputation is a deterrent….slaps on the wrist don’t achieve anything.

  12. Anonymous says:

    A** whoopings don’t fall out of the sky…

  13. Anonymous says:

    Slap on the wrist ..won’t change her ways, in a culture of high heels, long nails and no brains.

  14. Anonymous says:

    The ultimate in vanity
    Exploiting their supremacy
    I can’t believe the things you say
    I can’t believe, I can’t believe the price
    We pay
    Justice is lost, justice is raped, justice is gone
    Pulling your strings, justice is done
    Seeking no truth, winning is all
    Find it so grim, so true, so real

  15. Anonymous says:

    cayman justice= no justice

  16. Anonymous says:

    nice precedent…will look forward to meeting a few cops this weekend and settling a few scores.

  17. Anonymous says:

    Basically we can all agree now she wasn’t fit to be ambassador material. Will there be a disgorgement of benefits paid from us, back to our account?

  18. Equality does not exist says:

    Image if this was a young man with a history of violence do you think he would have received a suspended sentence?
    Disgraceful. Young men in Cayman take note of her and stay away.

    • 345Dude says:

      Agreed, no one truly wants equality in all aspect. I’d imagine if she was an Expat then she’d spend prison time and get deported right?

    • Anonymous says:

      Don’t worry she’ll be back in the dock or in the asylum in EE before her two years are up.
      She obviously has serious issues but acknowledgement is the first to dealing with them. Repeated lunacy is being rewarded with impunity. Who would have been accountable if she had critically injured or even killed someone?

    • Anonymous says:

      Women and men should be held to the same standard. Im a woman and even I think it’s unfair. The law should apply equally.

    • Anonymous says:

      yeah all the me-too brigade have gone silent….zzzzz


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