Trust funder accused of murdering his father over weekly allowance just wanted to make him proud him but 'nothing was ever good enough,' ex-girlfriend reveals

• Tommy Gilbert Jr was arrested after his father Thomas Gilbert Sr was found shot to death in his Upper East Side apartment on Sunday
• Investigators believe the younger Gilbert shot his father because his weekly allowance was about to be cut
• Anna Rothschild, who recently dated Tommy, was shocked to hear of the murder
• However, she says the father and son did have a strained relationship that haunted Tommy when they were dating

By Dailymail.com Reporter and Associated Press

Published: 18:37 EST, 6 January 2015 | Updated: 00:12 EST, 7 January 2015

The handsome high-society New Yorker accused of murdering his financier father was constantly struggling to appease him and felt like a disappointment, an ex-girlfriend has revealed.

Two-time divorcee Anna Rothschild recently dated alleged killer Tommy Gilbert Jr, and spoke to ABC News on Tuesday about the tortured father-son relationship.

Manhattan's elite enclave of the Upper East Side was rocked Sunday when 70-year-old Thomas Gilbert Sr was found shot dead in his apartment. Investigators believe his son carried out the killing because his weekly allowance was about to be cut.

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Former flame: Anna Rothschild (pictured) recently dated Tommy Gilbert Jr, the 30-year-old man accused of murdering his financier father over a weekly allowance

Motivations: Investigators believe Thomas Gilbert Jr (left) killed his father Thomas Gilbert Sr (right) because the elder wanted to cut down his son's weekly allowance

Gruesome: Above, investigators remove Thomas Gilbert Sr's body from his apartment building on Manhattan's Upper East Side

Miss Rothschild, 49, says she was shocked and surprised to hear her ex-boyfriend was implicated in his father's death, since Tommy seemed happy and 'totally fine' when she saw him at a dinner just two weeks ago.

However, she she was frank when she described his 'strained' and 'stressful' relationship with his father.

'His father was never happy with anything he did or nothing was ever good enough,' she said.

Miss Rothschild first met Tommy at a mutual friend's dinner party in December 2013, and soon after started dating. She says they broke up last May when she started dating someone new.

Broken up: The couple met at a mutual friend's party in December 2013. Pictured above last year at an event at The Jane Hotel. Miss Rothschild says they broke up last May after she started dating someone new

No bail: The 30-year-old was arraigned Monday on murder charges and jailed without bail. His attorney had no comment

Behind bars: Tommy seen being escorted into Manhattan Central booking by a police officer

At the time, Miss Rothschild says Tommy was unemployed but working to start his own hedge fund, just like his father.

In a separate interview with the New York Post, Miss Rothschild revealed that Tommy complained about his father not giving him the seed money to start the investment venture.

WHO IS TOMMY'S SOCIALITE EX? ANNA ROTHSCHILD'S COLORFUL PAST

Tommy Gilbert Jr's ex-girlfriend, Anna Rothschild (pictured), revealed details of alleged killer's troubled life on the day he was charged with the murder of his 70-year-old multimillionaire father.

'He's very much a loner. His phone never rang. No one texted him or called him. The one time it rang in four months while we were together it was his mother,' the 49-year-old told the Post on Monday.

The Manhattan socialite dated Gilbert Jr, who is 19 years her junior, for four months in early 2014 and last saw him at Christmas.

It's not the first time Ms Rothschild's colorful love life has drawn her into the public eye.

In October 2003, the former London-based interior designer claimed she was dating actor Alec Baldwin, WENN reported, but he laughed off rumors saying at the time that he was enamored with a 25-year-old trainee lawyer.

Several years before, Ms Rothschild, who gave her age as 31 but would have been 35, spoke of her love for large diamond rings to The New York Times as she divorced her second husband.

She told The Times that her first, stockbroker husband had given her a five-carat diamond ring from Harry Winston while the second, an English businessman, had trumped up a six-carat piece.'Personally, I would have preferred ten carats,' she said.

She's been married at least twice and her registered address is a small rental on the Upper East Side.

The 49-year-old is the founder of A. Rothschild & Co. PR company. On the firm's Facebook page, she describes herself as 'an MBA Columbia University graduate and one of the most sought after socialites on the Upper East Side, Ms. Rothschild owns one of the most reputable and successful Public Relations and Marketing firms in New York City'.

The website for the venture appeared to be now defunct. The last event posted to the firm's social media pages was on July 30.

According to court records, Ms Rothschild filed for bankruptcy in 2011 and 2013.

In 2012, Ms Rothschild was praising the benefits of taking a car service to Greenwich, Connecticut because of the hot dating scene in the suburbanite clubs.

She told The Post at the time: 'There’s so many guys! I don’t know which way to look.'

In winter 2012, she was rumored to be dating Prince Lorenzo Borghese, made famous by season nine of reality show The Bachelor.

The Italian royal, who actually hails from New Jersey and runs a pet-care company, threw a lavish New Year's Eve party with the socialite at a Park Avenue penthouse.

Still, money never seemed to be too much of an issue during their courtship since Tommy always paid the bill when they went out and seemed to enjoy his life of leisure.

Miss Rothschild says Tommy appeared not to be too bothered about his lack of a job, spending most of his time in the Hamptons, going to the gym, practicing yoga and surfing.

She describes Tommy as sweet but a bit of an introverted loner who had few friends.

In fact, Tommy's mother was about the only person who ever called him, Miss Rothschild says.

Still, she finds it hard to believe her former flame capable of carrying out such a heinous act.

'How could a guy be that gorgeous, that wealthy, that fit and kill his dad? This is the last thing in a million years that I thought he could do,' Miss Rothschild said.

Tommy Gilbert was part of the trust-fund-baby crowd, a handsome Princeton grad who flitted between his Manhattan home and the Hamptons and attended society parties at museums and symphonies while living off an allowance from his parents.

On the surface, it was a charmed life.

But he was in debt, with no job or recent work history. He was a suspect in a fire that destroyed a mansion on Long Island, a law enforcement official said. He was accused of harassing a friend. And his mother told police he had a tense relationship with his Wall Street father and a history of mental illness, authorities said.

On Sunday afternoon, police say, it all erupted in violence over a small amount of money.

Threatened with a cut of a few hundred dollars in his monthly allowance, Gilbert went to his parents' apartment on wealthy Beekman Place on Manhattan's East Side and shot his father to death, authorities said.

The 30-year-old was arraigned Monday on murder charges and jailed without bail. His attorney had no comment.

Gilbert had gone to his parents' home saying he wanted to have a word alone with his father, hedge fund founder Thomas Gilbert Sr. His mother went out to get him some food and was gone about 15 minutes when she got a "bad feeling" and went back, said Robert Boyce, chief of detectives.

She found her 70-year-old husband on the bedroom floor, a bullet hole in his head, Boyce said.

A .40-caliber Glock was resting on his chest, his left hand on the gun. Boyce said it was a staged to look like suicide, but the gun wasn't in the right position for a self-inflicted wound.

Detectives waited outside Gilbert Jr.'s $3,000-a-month apartment in a six-floor walkup in Chelsea. When they saw a light go on, they went in and found bullets and empty shell casings along with 21 blank credit cards and a device for stealing card numbers, police said.

"He was on a stipend from the family. Looks like he was in debt," Boyce said.

Gilbert was taken in for questioning but he refused to speak to detectives and asked for an attorney.

His father, a graduate of Princeton University and Harvard Business School, worked on Wall Street for more than 40 years and founded Wainscott Capital Partners Fund in 2011. The fund has $200 million in assets.

The shooting was a rare act of violence in the well-to-do neighborhood near the United Nations.

Neighbor Pierre Gazarian remembered Gilbert as "incredibly courteous, elegant," and praised his "civility."

Gilbert Jr. graduated from Princeton in 2009 with a degree in economics and was trying to follow in his father's footsteps: He had filed papers with the Securities and Exchange Commission to start a hedge fund of his own, Mameluke Capital.

He attended galas and fundraisers with the city's wealthy. In many society photos, some taken at such places as the Frick Collection and the New York Philharmonic, he was seen posing with smiling young women and looking tan at the beach.

But he was arrested and accused in September of harassing Peter N. Smith in the town of Southampton, on Long Island, and had a Feb. 2 court date. And a law enforcement official, who was not authorized to discuss the investigation and spoke to The Associated Press on condition of anonymity, said Gilbert is a suspect in a blaze that burned down Smith's father's mansion three days before his arrest.

Pattern of violence? Tommy was arrested and accused in September of harassing a Peter N Smith in Southampton, Long Island. A law enforcement official revealed that Tommy was suspected of burning down Smith's father's mansion there three days before his arrest