Donald Trump Jr and his habit for making headlines
The US president's son, Donald Trump Jr, joined his brother to take the reins of the family business as his father left New York to step into the presidential spotlight.
But Donald Trump's eldest son has failed to evade the Russian scandal that has engulfed Washington and his father's White House.
Mr Trump Jr, 39, raised eyebrows after he released an email chain showing he was offered damaging information "that would incriminate" Hillary Clinton by a Russian national during the 2016 election.
The fresh revelation came after he admitted to meeting Russian lawyer Natalia Veselnitskaya at Trump Tower with his sister's husband, Jared Kushner, and campaign manager Paul Manafort.
The Republican president has been dogged by allegations that Moscow tried to tip the election in his favour since he took office. He has repeatedly denied any knowledge of Russian interference.
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But the emails, which Mr Trump Jr pre-emptively released on Twitter ahead of a New York Times report, appeared to be the first confirmation that a senior Trump associate met a Russian official with the expectation of being handed sensitive material.
Donald Trump Jr is the eldest of three children from Mr Trump's first marriage to Ivana.
Born in 1977, he grew up in his family's gilded penthouse at Trump Tower in Manhattan and was just 12 years old during his parents' highly publicised divorce
He attended the Hill School in Pottstown, Pennsylvania, and later followed in his father's footsteps at the Wharton School at the University of Pennsylvania.
But he briefly departed from the familial path to serve as a bartender in Aspen, Colorado, after he graduated from college in 2001.
Later that year Mr Trump Jr went to work for the Trump Organization and - like his sister Ivanka - would rise to become executive vice-president, overseeing acquisitions and new developments for the firm's real estate, hotels and golf courses.
He also appeared alongside his siblings as advisers on his father's reality television programme The Celebrity Apprentice.
Mr Trump Jr married his wife, Vanessa Haydon, in November 2005 after his father introduced the pair at a fashion show two years earlier.
The couple have five young children together: Kai, Chloe, Donald, Tristan and Spencer.
Since his father took office, Mr Trump Jr and his brother, Eric, have taken control of management of the family firm.
But the first-born Trump has also shown interest in continuing his family's political legacy.
During a CNN interview in July 2016, he said he would not rule out a run for New York mayor, adding: "As my father always said...we always like to keep our options open".
Mr Trump later cast doubt on the idea, telling Fox News: "I don't see that happening."
Though he was raised among the posh high-rises and busy streets of New York City, Mr Trump Jr has long had an affinity for outdoor life.
At an early age, he developed a close relationship with his maternal grandfather, Milos Zelnicek, with whom he spent several weeks during the summer camping, fishing and hunting in a town outside Prague.
During his time visiting his grandparents, he also learned to speak Czech.
Mr Trump Jr and his Eric Trump's penchant for hunting big game also came under scrutiny in 2012 after photos surfaced showing the pair in Zimbabwe posing with dead animals including a leopard and a crocodile.
The brothers defended themselves, noting that they were not hunting illegally.
"Hunting forces a person to endure, to master themselves, even to truly get to know the wild environment," he later said in a Forbes interview in 2012. "Actually, along the way, hunting and fishing makes you fall in love with the natural world."
Known as a fierce defender of the family name, Donald Trump Jr has made headlines for a string of controversial remarks he made since his father entered the political realm.
During an interview last September, he said the media would be "warming up the gas chamber right now" if Republicans acted the way Democrats did.
The remarks drew outrage from the Anti-Defamation League, which said he was trivialising the Holocaust. But Mr Trump Jr later said he was referring to capital punishment.
Much like his father, he has used social media to both rail against his family's critics and praise the Trump administration.
In March Mr Trump Jr incensed some British people on Twitter when he lambasted London's mayor after the terror attack on Westminster, which killed three people.
Last September he posted a controversial graphic that likened Syrian refugees to poisoned Skittles, with the caption: "Would you take a handful? That's our Syrian refugee problem." He later deleted the graphic.
He also came under fire for posting an image on Instagram that altered a version of the movie poster for The Expendables, which included the online cartoon character Pepe the Frog depicted as his father.
The internet meme has been characterised as a symbol of hate and used by the alt-right group, a disparate group of right-wingers.