Wealthy ‘playboy’ financier hit with multiple domestic violence charges against glamorous ex-girlfriend
A high-profile Sydney eastern suburbs financier has appeared in court accused of assaulting his 21-year-old socialite ex-girlfriend.
Thomas Christopher Fennell, 53, was arrested on domestic violence charges over alleged incidents involving Mackenzie Bridgewood, 21, five-and-a-half months ago.
Fennell has previously attracted attention over his lavish life, including an extravagant 50th birthday party in 2023 that was reportedly Playboy Mansion themed.
It’s understood Ms Bridgewood reported the allegations at Maroubra Police Station on Friday.
The couple began dating last year and broke up in June this year.
Fennell has been accused of six DV charges including two counts of common assault occasioning actual bodily harm and two counts of common assault, the Daily Telegraph reported.
Ms Bridgewood is understood to be pregnant with her second child, however, Fennell’s lawyer told the court on Sunday he has not been confirmed as the father.
The judge granted Fennell bail to live at his multi-million dollar Bellevue Hill property, despite opposition from the prosecution.
MIllionaire financier Tom Fennell (right) has been accused of assaulting his 21-year-old socialite ex-girlfriend, Mackenzie Bridgewood (left)
Fennell (above) fronted a bail court on Sunday on six domestic violence charges
His case will return to Waverley Court on November 12.
Fennell’s lawyer, Paul McGirr, confirmed he will fight the charges.
‘The allegations are strenuously denied and will be vigorously defended,’ he said.
Fennell – once considered one of Sydney’s most eligible bachelors following his split from ex-wife Vanessa Jacobs Fennell – has been quiet on Sydney’s social scene since he and Bridgewood parted ways.
Sources close to Fennell say he and Bridgewood have not crossed paths since they broke up, despite her move from Sydney’s inner west to her grandparents’ home at Darling Point in the exclusive eastern suburbs.
Bridgewood previously enjoyed a jet-setting lifestyle after linking up with Fennell, spending time at his Bellevue Hill party pad and travelling first-class to Paris and Switzerland.
Since splitting from Fennell, she was rumoured to be linked with another businessman believed to be in the middle of a high-profile separation.
Fennell’s and Bridgewood’s relationship attracted attention not only because of the significant age gap, but also because of her striking resemblance to his late former fiancée, socialite Annabelle Price.
It’s understood Bridgewood (above) made a report to police on Friday
Price, 32, died in non-suspicious circumstances in March.
His ex-wife Vanessa, 55, made headlines last year after crashing her Range Rover into a parked Tesla following a social luncheon and then assaulting a police officer who arrived on the scene.
She later pleaded guilty to negligent driving, assaulting police, refusing a breath test and failing to provide her particulars to the owner of the damaged property.
She formally entered pleas at Waverley Local Court in May 2025, but is still seeking to have the matters dealt with under mental health provisions.
READ MORE: Why playboy Tom Fennell’s romance with a 21-year-old ended in tears after an Emirates flight that had cabin crew talking
