Is Donald Trump Jr. Married? Inside the Life of America’s First Family

As the eldest son of Donald Trump, Donald Trump Jr. has been in the public eye since birth. His personal relationships and family life have drawn much interest over the years. Many are curious – who is married to Donald Trump Jr.?

Let’s take an in-depth look at Donald Jr.’s current wife, his past marriages, children, and the dynamics of the Trump family.

Donald Trump Jr.’s Current Wife

Donald Trump Jr., often referred to as Don Jr., has been married to Vanessa Trump (maiden name: Vanessa Kay Haydon) since 2005. Key facts about Vanessa:

  • Born in 1977 and grew up in New York City as the daughter of Bonnie and Charles Haydon.
  • Met Don Jr. at a fashion show in 2003 where she worked as a model.
  • Married Don Jr. in November 2005 at Mar-a-Lago in Palm Beach, Florida.
  • Has five children with Don Jr. – daughters Kai, Chloe, and Spencer, and sons Donald III and Tristan.
  • Lived a relatively low-key life compared to other members of the Trump family.
  • Filed for divorce from Don Jr. in March 2018 after 12 years of marriage.

Vanessa maintained a modest public profile during her marriage to Don Jr. She focused on raising their children while he ran the Trump Organization with his brother Eric.

Don Jr.’s Divorce from Vanessa

In March 2018, Vanessa Trump filed for divorce from Donald Trump Jr. after 12 years of marriage. Some key points about their split:

  • Vanessa cited “unresolvable differences” as reason for the divorce.
  • The divorce was uncontested with a settlement reached quickly and privately.
  • Don Jr. and Vanessa issued a joint statement saying their focus was on their children.
  • Many sources reported they separated before President Trump took office.
  • Rumors of Don Jr.’s affair with Celebrity Apprentice contestant Aubrey O’Day in 2011 emerged after the filing.
  • Don Jr. took over managing the Trump Organization after the divorce.

Despite rumors of affairs, the divorce appeared amicable without a contentious legal battle. Don Jr. and Vanessa agreed to joint custody of their five children.

Donald Trump Jr.’s New Relationship

In early 2019, Donald Trump Jr. began dating Kimberly Guilfoyle, a TV personality who worked on Fox News and was an assistant to Donald Trump during his 2016 campaign. Key facts about Kimberly:

  • Born in 1969, she is 9 years older than Don Jr.
  • Previously married twice – to California politician Gavin Newsom and furniture heir Eric Villency.
  • As a lawyer, she served as an Assistant District Attorney in San Francisco.
  • Spent several years as legal analyst on TV shows including The O’Reilly Factor.
  • Joined Fox News in 2006 as a news anchor and host.
  • Left Fox News in 2018 amid accusations of misconduct, which she denied.
  • Started dating Don Jr. soon after he separated from Vanessa Trump.
  • Works on fundraising operations for President Trump’s re-election campaign.

The couple appear regularly together at political events and trips. Don Jr. has praised Kimberly’s intelligence and made her a key part of his political inner circle.

Donald Trump Jr.’s Ex-Wife Relationships

Donald Trump Jr. has one known former partner prior to his marriage to Vanessa Trump – model Melissa Ann “Missy” Leigh. Key facts:

  • Don Jr. dated Missy Johnson for 5 years beginning in 1998.
  • She was a model who appeared in some Guess clothing ads.
  • Lived with Don Jr. for 3 years, spending time in New York and at Mar-a-Lago.
  • Don Jr. reportedly broke up with her via FedEx letter.
  • She later married actor Gary Harrison Leigh.

Don Jr.’s relationship history before Vanessa Trump remains relatively unknown. But his gentlemanly breakup letter to Missy Johnson hinted at his immaturity early in life before settling down.

Donald Trump Jr.’s Prominent Role in the Trump Family

As the eldest son bearing his father’s name, Don Jr. serves an important role in the Trump family empire and politics:

  • Took over with brother Eric Trump running the Trump Organization in 2017 after Donald Trump became President.
  • Became a passionate advocate and attack dog for his father on the campaign trail and media.
  • Key speaker at Republican events, praising his father’s policies and achievements.
  • Active on conservative social media defending President Trump’s record.
  • Published book “Triggered” supporting his father’s agenda.
  • Rumored to have political aspirations of his own, including a possible run for NYC mayor.

Don Jr. arguably became the second most prominent Trump family member in politics after his father due to his zealous promotion of Trumpism.

Donald Trump Jr.’s Relationship with His Parents

By all accounts, Donald Trump Jr. has a close and loving relationship with both of his parents:

Father Donald Trump

  • Don Jr. inherited his father’s strong personality, confidence, speaking style and passion for business.
  • They share a deep interest in conservative politics and Don Jr. idolizes his father’s successes.
  • Don Jr. has worked for the Trump Organization since graduating college in 2000.
  • The two share a love of hunting, fishing, golf and real estate development.
  • Don Jr. became an aggressive defender of his father against media attacks.

Mother Ivana Trump

  • Ivana raised Don Jr. and siblings mostly as a single mom after divorcing Donald Trump in 1992.
  • She instilled a strong work ethic and helped oversee the children’s education and upbringing.
  • Ivana remains very involved in her children’s lives as grandmother to 10 grandchildren.
  • They appear to have an affectionate, playful mother-son relationship into adulthood.

Don Jr. speaks reverently of both his mother and father as major influences in his life despite their divorced households.

The Role of Donald Trump Jr.’s Siblings

Donald Trump Jr. has two younger siblings who have also been prominent parts of the Trump family.

Ivanka Trump

  • Don Jr.’s younger sister Ivanka was born in 1981.
  • The two were close growing up and she has played a key role in the Trump Organization and politics.
  • Known for her fashion, accessories businesses and poise, contrasting Don Jr.’s controversial style.
  • Rumored tensions developed as Don Jr. accused her of attempting to undermine his power.

Eric Trump

  • Eric Trump, born in 1984, works closely with Don Jr. running the Trump family company.
  • The two brothers inherited responsibility for the business from their father.
  • Don Jr. and Eric host a podcast together focused on political issues.
  • They share a close personal and working relationship into adulthood.

Don Jr. appears to collaborate well with his sister Ivanka and brother Eric, despite some reported competitiveness and disagreements at times behind the scenes.

Life as a Father

An important part of Donald Trump Jr.’s life centers around his five children:

  • Daughter Kai, born in 2007
  • Daughter Chloe, born in 2014
  • Daughter Spencer, born in 2020
  • Son Donald III, born in 2009
  • Son Tristan, born in 2011
  • Co-parents the kids with ex-wife Vanessa Trump

Don Jr. posts frequently on social media about his children, sharing family photos from trips and events. He seems proud and engaged as a father. Balancing frequent travel, political activities, new girlfriend Kimberly and his kids makes for a hectic life.


Donald Trump Jr. navigated divorce from wife Vanessa in 2018 and soon began dating Fox personality Kimberly Guilfoyle. He maintains busy careers in business and politics alongside his father while co-parenting five children from his first marriage. Don Jr. enjoys tight-knit relationships with his siblings Ivanka and Eric as well as his parents. His active support for Donald Trump’s agenda makes Don Jr. one of the most influential and vocal surrogates for the Trump family.


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Nakashima, Ryan and Alan Suderman. “Unlike the president, Donald Trump Jr. showed up for jury duty.” Chicago Tribune, November 8, 2019.

Santucci, John and Katherine Faulders. “Inside the lives of Donald Trump’s 5 children, 9 years after ‘Apprentice’ made him a household name.” ABC News, January 20, 2017.

Scott, Eugene. “Donald Trump Jr. has book out later this year.” CNN, May 22, 2019.

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Tumulty, Karen. “Donald Trump Jr. settles long divorce with Vanessa.” The Washington Post, February 8, 2022.

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