Early Life and Education of Donald Trump Jr.: A Complete Timeline

By Popular Timelines Editorial Team · Updated: April 12, 2026

An overview of the childhood and early education of Donald Trump Jr., highlighting the experiences that shaped the journey.

Donald John Trump Jr., is an American businessman and activist, known as Don Jr. He is the eldest son of Donald Trump. He is also politically active, frequently appearing at rallies and conferences, and he's a prominent figure in conservative media. Trump Jr. has been involved in various business ventures, often working within the Trump Organization.

Sections (4)

Full Timeline Early Life & Education Career & Achievements Controversies & Scandals

December 31, 1977: Donald Trump Jr. Born

On December 31, 1977, Donald John Trump Jr., son of Donald Trump and Ivana Trump, was born. He is an American businessman and activist often nicknamed Don Jr.

2000: Moved to Aspen, Colorado after Graduating from Penn

After graduating from Penn in 2000, Donald Trump Jr. moved to Aspen, Colorado, where he hunted, fished, skied, lived in a truck, and worked as a bartender for a year.

2000: Graduated from Wharton School

In 2000, Donald Trump Jr. graduated from the University of Pennsylvania's (Penn) Wharton School with a B.S. in Economics.

2003: Began dating Vanessa Haydon

In 2003, Donald Trump Jr. began dating model Vanessa Kay Haydon at his father's suggestion.

November 12, 2005: Marriage to Vanessa Haydon

On November 12, 2005, Donald Trump Jr. married model Vanessa Kay Haydon at his father's Mar-a-Lago estate in Palm Beach, Florida. The service was officiated by his aunt, Judge Maryanne Trump Barry.

May 2007: Birth of daughter Kai Madison

In May 2007, Donald Trump Jr. and Vanessa Haydon welcomed their first child, a daughter named Kai Madison.

2007: Donated to Hillary Clinton's Campaign

In 2007, Donald Trump Jr. gave $4,000 to then-Senator Hillary Clinton's campaign to be the Democratic presidential nominee.

February 2009: Birth of son Donald John III

In February 2009, Donald Trump Jr. and Vanessa Haydon welcomed their second child, a son named Donald John III.

2010: Hunting trip where trophy photos were taken

In 2010, Donald Trump Jr. took photos of his hunting trophies, which were later published in 2012, sparking controversy. In one photo, Trump Jr. is pictured with his arms around a dead leopard.

October 2011: Birth of son Tristan Milos

In October 2011, Donald Trump Jr. and Vanessa Haydon welcomed their third child, a son named Tristan Milos.

October 2012: Birth of son Spencer Frederick

In October 2012, Donald Trump Jr. and Vanessa Haydon welcomed their fourth child, a son named Spencer Frederick.

2012: Controversy over hunting trophy photos

In 2012, controversy erupted when photos Donald Trump Jr. had taken of his hunting trophies in 2010 were published, including one where he is holding a knife in one hand and a bloody elephant tail in the other. Anti-hunting activists criticized him, although the hunt was legal.

June 2014: Birth of daughter Chloe Sophia

In June 2014, Donald Trump Jr. and Vanessa Haydon welcomed their fifth child, a daughter named Chloe Sophia.

2015: Mia Farrow reposts hunting photos

In 2015, Mia Farrow reposted the pictures Donald Trump Jr. had taken of his hunting trophies, further fueling the controversy that erupted in 2012.

September 2017: Asked to Remove Secret Service Detail

In September 2017, Donald Trump Jr. asked to have his Secret Service detail removed, citing a desire for more privacy, but the protection was later restored.

2017: Prairie dog hunting trip in Montana

On Earth Day in 2017, Donald Trump Jr. legally hunted prairie dogs in Montana with GOP Congressional candidate Greg Gianforte.

March 15, 2018: Separation from Vanessa Haydon Announced

On March 15, 2018, it was announced that Donald Trump Jr. and Vanessa Haydon had separated, and Haydon had filed for uncontested divorce in Manhattan Supreme Court.

2018: Started dating Kimberly Guilfoyle

In 2018, Donald Trump Jr. started dating Kimberly Guilfoyle, who had been friends with the Trump family for years.

February 22, 2019: Divorce Settlement Announcement

On February 22, 2019, Donald Trump Jr. and Vanessa Haydon announced that they had settled their divorce at the end of 2018.

December 11, 2019: Mongolia hunting permit controversy revealed

On December 11, 2019, ProPublica revealed that the government of Mongolia retroactively granted Donald Trump Jr. a hunting permit for the endangered Argali mountain sheep. The sheep hunt and travel to Ulaanbaatar for a private meeting with Mongolian president Khaltmaagiin Battulga cost U.S. taxpayers $76,859.36 for United States Secret Service protection.

2019: Developed Persona as Right-Wing Provocateur

By 2019, Donald Trump Jr. had developed a "public persona as a right-wing provocateur and ardent defender of Trumpism", according to The Washington Post.

2019: Mia Farrow reposts hunting photos again

In 2019, Mia Farrow reposted the pictures Donald Trump Jr. had taken of his hunting trophies, which previously caused controversy in 2012, again.

February 2020: Alaska hunting trip with fundraising auction winner

In February 2020, Donald Trump Jr. agreed to go on a hunting trip in Alaska with the winner of a fundraising auction for Safari Club International.

December 31, 2020: Engagement to Kimberly Guilfoyle

On December 31, 2020, Donald Trump Jr. reportedly became engaged to Kimberly Guilfoyle on his 43rd birthday.

December 2021: Switched official residency to Florida

In December 2021, Donald Trump Jr. switched his official residency from New York to Florida, two years after Donald Trump had done so.

January 2022: Public Announcement of Engagement to Kimberly Guilfoyle

In January 2022, the news of Donald Trump Jr.'s engagement to Kimberly Guilfoyle was made public.

2024: Mutual End of Engagement with Kimberly Guilfoyle

In 2024, Donald Trump Jr. and Kimberly Guilfoyle mutually ended their engagement.

2024: Kai Trump Spoke at the Republican National Convention

In 2024, Kai Trump, Donald Trump Jr.'s oldest daughter, spoke at the Republican National Convention on July 17.

December 2025: Engagement to Bettina Anderson

In December 2025, it was announced that Donald Trump Jr. had become engaged to socialite Bettina Anderson.

2025: Accusation of killing protected duck in Venice lagoon

In February 2025, Donald Trump Jr. was accused of killing a protected duck while hunting in the Venice lagoon. A video showed Trump Jr with the body of a rare ruddy shelduck (Tadorna ferruginea), a species protected throughout Europe and by Italian law.