Suspicions over blaze revealed as ex details his dark past and how he 'was never good enough' for his dad

Anna Rothschild (pictured right with Tommy Gilbert Jr.) says the 30-year-old Princeton graduate resented his father 70-year-old Tommy Gilbert Sr. and how controlling he was over his money. Gilbert Jr. appeared in court on Monday (pictured left) to answer changes of second-degree murder and posession of a weapon after he allegedly shot dead Gilbert Sr. in his Manhattan home in a dispute over cutting his allowance from $600 a month to $400, according to reports. Gilbert Jr. is also reportedly the prime suspect in the september 1 arson that demolished a 19th century mansion in the Hamptons (top left) that belonged to the father of a love rival.

Suspicions over blaze revealed as ex details his dark past and how he 'was never good enough' for his dad...

A Princeton graduate who was Monday charged with murdering his millionaire father and then trying to stage it as a suicide is also the prime suspect in an arson that burned down a rival's centuries-old Hamptons mansion, it has been revealed.

Tommy Gilbert Jr was arrested in September for violating a restraining order taken out by Peter N. Smith, days after Smith's father's home went up in flames in an arson attack. 

Gilbert Jr was on Monday charged with shooting his father dead at a luxury Manhattan apartment in a fight over his allowance - then trying to make the killing look like a suicide. 

The 30-year-old Ivy Leaguer was a mainstay at New York society blacktie events. But one ex-girlfriend tells of how he had a dark side. A 49-year-old socialite he dated last year says he was a loner with few friends who deeply resented his father Thomas Gilbert Sr. and was obsessed with how he would 'never be good enough' for his dad. 

Reports are also beginning to emerge that Gilbert Jr. suffered from mental illness and had been off his medication prior to the shooting.  

Tommy Gilbert Jr, 30, appeared in court on Monday to answer charges of murder and criminal possession of a weapon following the shooting death of his father on Sunday


Gilbert Jr.'s ex-girlfriend Anna Rothschild, 49, says he was a loner whose phone only rang when his mother called. The two are pictured together at a charity gala at the Jane Hotel in last January 

Cops say Gilbert Jr visited the Midtown Manhattan home, asked his mother to go and buy a sandwich, shot his father dead and left the gun in the victim's left hand to make it look like a suicide before fleeing. 

Police later found the box the gun came in and ammunition that matched the murder weapon at Gilbert Jr's home, investigators said. 

The New York Post reports that Gilbert Jr. is the prime suspect in the September 15 blaze that demolished a historic 19th century mansion in Sagaponack in the Hamptons. 

No one has been arrested or charged, however, a gas can and gasoline-soaked cloth was found in a nearby cemetery and Southampton police are investigating the case as an arson. 

Gilbert Jr.'s ex girlfriend - twice-divorced Upper East Side socialite Anna Rothschild - told the Post that her former flame was a loner who had few friends and never got phone calls.

The only person who ever called him was his mother, Miss Rothschild says. 

Gilbert Jr. was jobless - and seemed to have few prospects, and little interest, for finding serious work.

Instead, he spent most his time in the Hamptons, going to the gym, doing yoga and surfing. 

'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, 49, told the Post. 

His one professional aspiration was founding his own hedge fund - but he complained that his father wouldn't give him the seed money to start it, Miss Rothschild said. 

Gilbert Jr. has an investment company registered to his $2,400-a-month Chelsea apartment - though it's not clear the firm has any assets under investment. 

The company is a called Mameluke Capital - mamelukes being 13th-century Muslim slave soldiers. 

Miss Rothschild said Gilbert Jr. was also preoccupied with how controlling his father was over his money and was convinced that he could never do anything to gain his approval. 

'He talked a lot about his dad and how mean he was to him and how nothing was good enough,' she told the Post. 

The Post reports that Gilbert Jr. suffered from severe obsessive-compulsive disorder and was off his medication when he the murder happened, according to police sources.  

The first thing multiple acquaintances said of Gilbert Jr when asked to comment by Daily Mail Online on their fellow Princeton or Deerfield alumnus was the rumor that he'd burned down his one-time friend's house last summer.

Additionally a long-time resident of East Hampton and acquaintance of Gilbert Sr., who was a member of the upscale Maidstone Club there, also repeated the allegation.

The home belonged to Peter Smith Sr., a friend of the Gilbert family. The Post reports that Gilbert Jr. had been friends with Peter Smith Jr. - but that they had fallen out over a girl. 

The Post also claims that Gilbert Jr. Killed Smith's dog - but this was denied to Daily Mail Online by sources close to the events. 

Three days after the fire, on September 18, Gilbert Jr. was arrested for violating an order of protection taken out by Smith Jr. 

Peter Smith Jr, 32, declined to comment on the allegations and his sister, Bettina Prentice, did not respond to requests for comment. 

Both the Gilbert and Smith families were members of the elite Maidstone Country Club. The 120-year-old establishment sits in the village of East Hampton and has sweeping ocean views along with a private beach, tennis house and 18-hole golf course.

Former golfers on the links included Jacqueline Kennedy's father, John Vernou 'Black Jack' Bouvier III, and socialite Edith Bouvier Beale, famed from 'Grey Gardens.'

The Post reports that Gilbert Jr. had been banned from the club after a fight there. 

Southampton Police detective Lisa Costa told Daily Mail Online on Monday that the house was destroyed in an arson attack and that there were no injuries. 

She refused to comment further with regards an ongoing investigation. No one has been charged in the alleged attack. 

Southampton Fire Department refused to comment to Daily Mail Online on Monday.  

Tommy Gilbert Jr was arrested at his home on Sunday night in the Chelsea neighborhood of Manhattan, following the fatal shooting of his father, the founder of hedge fund, Wainscott Capital.

The 30-year-old was being held pending arraignment and the law office representing him had no comment.

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 Miss Rothschild's colorful love life has drawn her into the public eye.

In October 2003, the former London-based interior designer claimed that 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, Miss 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.  

The Upper East Side divorcee 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.

The 49-year-old is the founder of A. Rothschild & Co. PR company. 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.

More than a decade later 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. 

Source: Ex details his dark past and how he was never good enough for his dad