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According to Gomes’ ruling, a copy of which was provided to the Star, Holmes was working in the downtown 52 Division in 2017 when he stopped a cyclist for running a red light. When the cyclist refused to provide identification, Holmes moved to handcuff and arrest him, pushing him to the ground and breaking his collarbone and one of his big toes.

Holmes began working for the service in 2008 as a cadet in training and was sworn in as an officer the following year.

At a tribunal hearing this May, Gomes heard the constable faced his first formal discipline in 2012, when he was found guilty of misconduct for posting a picture on Facebook that showed a police officer holding a baton with the words “I’m gonna kick your a-- and get away with it.” He was made to forfeit one day’s pay as penalty.

In the 2017 case involving the cyclist, the Special Investigations Unit, a provincial watchdog that investigates incidents involving police where there is serious injury or death, charged Holmes with assault causing bodily harm. He was convicted in 2019 and sentenced to one year of probation. His appeal of the conviction was denied.

In 2018, while awaiting trial on the criminal charge and on restricted duties, Holmes was leaving a parking lot on Simcoe Street in his black Corvette when a cyclist travelling in the wrong direction forced him to come to a sudden stop. Identifying himself as a police officer, Holmes used “profane, abusive and insulting” language towards the man, including the comments about millennials.
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Holmes was also found guilty of discreditable conduct for berating a different cyclist while off duty, declaring “all millennials are d--ks” and “this is a whole generation of f--k-ups,” according to Gomes’ ruling.

The other charges he was found guilty of were misconduct and insubordination for using “profane, misogynistic and racist” language in “inappropriate” and at times “threatening” emails and texts to other members of the service, including calling a professional standards investigator assigned to several of his cases a “c--t” in an email.
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[His lawyer] told the tribunal that Holmes suffered serious illness, detailing diagnoses of post-traumatic stress disorder, major depressive disorder and alcohol use disorder he said were a result of Holmes’ police work, which the officer noted in his WSIB claim included attending suicides, death investigations and being exposed to HIV.