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Is Tiffany Trump the new Ivanka? Here's how the two first daughters stack up against each other

Considering Ivanka already has one step out of the door when it comes to her father's politics, it is possible Tiffany is looking to fill her shoes
UPDATED APR 12, 2023
Tiffany Trump (L) could very well replace Ivanka Trump (R) as former President Donald Trump's right-hand daughter (Chip Somodevilla & Riccardo Savi/Getty Images)
Tiffany Trump (L) could very well replace Ivanka Trump (R) as former President Donald Trump's right-hand daughter (Chip Somodevilla & Riccardo Savi/Getty Images)

MIAMI, FLORIDA: Ivanka Trump's absence from her father's post-indictment speech at Mar-a-Lago last week definitely raised eyebrows - after all, many consider her to be Donald Trump's favorite child. However, those attending the prime-time event couldn't help but notice that his other daughter, Tiffany Trump, was front and center for the occasion. Could this mean she's making a foray into politics?

Considering Ivanka, 41, already has one foot out of the door when it comes to her father's politics, insiders with knowledge recently told the New York Post that Tiffany was "trying to be the supportive daughter." They noted that while she has "never really been involved in the political stuff," this "could be her way to get closer to her father." 

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Twenty nine-year-old Tiffany is Trump's daughter with his second wife Marla Maples. While she has somewhat been absent from her father's White House career, she did appear at the 2016 and 2020 Republican National Conventions, his swearing-in ceremony, his State of the Union address, and a few other events. Ivanka, on the other hand, has been a strong presence in her father's political campaigns and even served as an advisor to the president during her father’s tenure.

Republican presidential candidate Donald Trump, Ivanka Trump and Tiffany Trump stand during the third day of the Republican National Convention on July 20, 2016 at the Quicken Loans Arena in Cleveland, Ohio. Republican presidential candidate Donald Trump received the number of votes needed to secure the party's nomination. An estimated 50,000 people are expected in Cleveland, including hundreds of protesters and members of the media. The four-day Republican National Convention kicked off on July 18.
Republican presidential candidate Donald Trump, Ivanka Trump, and Tiffany Trump stand during the third day of the Republican National Convention on July 20, 2016, at the Quicken Loans Arena in Cleveland, Ohio (Photo by Jeff Swensen/Getty Images)

But the elder daughter, whom he had with Ivana Trump, officially stepped back from politics in November shortly after her father announced his third run at the White House. “I love my father very much," she said in a statement. "This time around, I am choosing to prioritize my young children and the private life we are creating as a family. I do not plan to be involved in politics.” With the prospect of Tiffany potentially replacing her older half-sibling in the Trump 2024 campaign, here's how the two first daughters stack up against each other:

Education

Tiffany Trump attended Viewpoint School in Calabasas, California, and graduated in 2012. She then attended the University of Pennsylvania -- where her father also studied -- and graduated in 2016 with a Bachelor of Arts degree in sociology with a concentration in law and society. She was also a member of the Kappa Alpha Theta sorority chapter at the university. Trump's youngest daughter subsequently entered Georgetown University Law Center in Washington, D.C., and came out with a Doctor of Jurisprudence (JD) degree in May 2020.

(L-R) Tiffany Trump and Ivanka Trump arrive on the West Front of the U.S. Capitol on January 20, 2017 in Washington, DC. In today's inauguration ceremony Donald J. Trump becomes the 45th president of the United States.
(L-R) Tiffany Trump and Ivanka Trump arrive on the West Front of the U.S. Capitol on January 20, 2017, in Washington, DC (Photo by Chip Somodevilla/Getty Images)

Meanwhile, Ivanka attended Christ Church and the Chapin School in Manhattan until age 15 before switching to Choate Rosemary Hall in Wallingford, Connecticut. She graduated from Choate in 2000 and went on to attend Georgetown University for two years before transferring to the Wharton School of the University of Pennsylvania, where she graduated cum laude with a bachelor's degree in economics in 2004.

Career

Tiffany originally aspired to become a singer and released a single in 2011 called 'Like A Bird'. During an appearance on The Oprah Winfrey Show, she said she was considering taking her music career "to the next level as a professional" but it never materialized. In 2015, she interned for Vogue, and the following year she modeled for an Andrew Warren fashion show during New York Fashion Week. Tiffany eventually entered Georgetown Law and has remained with the institute after graduating in 2020, working as a research assistant for Professor Shon Hopwood.

Marla Maples (L) and her daughter Tiffany Trump arrive at the 12th Annual Young Hollywood Awards at the Wilshire Ebell Theatre on May 13, 2010 in Los Angeles, California.
Marla Maples (L) and her daughter Tiffany Trump arrive at the 12th Annual Young Hollywood Awards at the Wilshire Ebell Theatre on May 13, 2010, in Los Angeles, California. (Photo by Kevin Winter/Getty Images)

By comparison, Ivanka has had a rather eventful career. She began modeling at the age of 14 and debuted in a Tommy Hilfiger denim campaign. In 1997, the Elite Model Management Corp. helped her feature on the cover of Seventeen magazine. For the next two years, the 5’10" blonde beauty traveled across the globe walking runways for the likes of Thierry Mugler, Jill Stuart, and Vivienne Westwood. She eventually gave up modeling and entered the reality TV business. Aside from her tenure as a judge on 'The Apprentice', she also provided commentary for the Miss Teen USA pageant.

Ivanka worked alongside her father and went on to collaborate with the season 5 Apprentice winner Sean Yazbeck to develop the Trump SoHo Condominiums. She later served as a guest judge on two seasons of 'Project Runway'. Then, in 2007, Trump's oldest daughter partnered with Dynamic Diamond Corp. to create Ivanka Trump Fine Jewelry, which went on sale at her flagship store in Soho. In 2011, she launched her namesake clothing line tailored for professional women.

Ivanka Trump attends the Young Fellows of The Frick Collection Annual Gala on March 13, 2008 in New York City.
Ivanka Trump attends the Young Fellows of The Frick Collection Annual Gala on March 13, 2008, in New York City. (Photo by Andrew H. Walker/Getty Images)

Ivanka became a part of the Trump Organization in 2005 and worked alongside her brothers, Eric and Don Jr, on the 25th floor of Manhattan's Trump Tower. She reportedly specialized in acquisitions and designs and was instrumental in the 2011 purchase of Doral Resort & Spa in Miami and revamping the Old Post Office Pavilion in Washington, D.C., to become the Trump International Hotel. After her father's 2016 presidential victory, Ivanka was appointed as a senior advisor in the Trump administration. She devotedly served her father throughout his tenure and became the face of various social campaigns and rallies. Since leaving Washington in 2021, Ivanka and her husband Jared have been living in Surfside, Florida.

Dating Lives and Spouses

Tiffany Trump recently tied the knot with her husband Michael Boulos, a Lebanese-American billionaire heir whose family reportedly owns Boulos Enterprises and SCOA Nigeria in Nigeria. The pair reportedly met in the summer of 2018, while Tiffany was on vacation in Greece with actress Lindsay Lohan. The pair were first romantically linked in November 2018, less than one year after she split from her boyfriend of two years Ross Mechanic. Tiffany and Michael were married on November 12, 2022, at Mar-a-Lago in Palm Beach, Florida.

(L-R) Tiffany Trump and Michael Boulos attend the Taoray Wang front row during New York Fashion Week: The Shows at Gallery II at Spring Studios on February 9, 2019 in New York City.
(L-R) Tiffany Trump and Michael Boulos attend the Taoray Wang front row during New York Fashion Week: The Shows at Gallery II at Spring Studios on February 9, 2019, in New York City. (Photo by Noam Galai/Getty Images for Taoray Wang)

Contrary to her younger half-sister, Ivanka has reportedly had a long list of boyfriends, from entrepreneurs to athletes to actors, per Hello! magazine. Investment banker Greg Hersch was Ivanka's first college boyfriend after the pair met at Georgetown University when they were both students. They broke up in 2001 but managed to remain friends. Ivanka then dated film producer James Gubelman for four years. The pair, who belonged to the same social circle in New York City, eventually parted ways in 2005.

Bingo Gubelman and Ivanka Trump arrive at the CFDA & Vogue Fashion Fund Dinner October 14, 2004 in New York City.
Bingo Gubelman and Ivanka Trump arrive at the CFDA & Vogue Fashion Fund Dinner on October 14, 2004, in New York City. (Photo by Bryan Bedder/Getty Images)

Rumor has it that Ivanka briefly dated Lance Armstrong. The pair reportedly met in 2006 when the Trump heiress was on a trip to Los Angeles. In 2007, however, Ivanka was linked to Sean Brosnan, the son of Pierce Brosnan. And right before meeting Jared, Ivanka was reportedly dating Justin Murdock the heir to the Dole Fruit fortune who has also been linked to Lana del Rey and Avril Lavigne. Ivanka finally met Jared in 2007 after being set up by a mutual friend. They reportedly broke up briefly due to religious differences but Ivanka converted to Judaism in 2009 and the couple got married that same year in New Jersey.

Children

As mentioned, Tiffany Trump and Michael Boulos got married in November 2022 at Mar-a-Lago in Palm Beach, Florida. They do not have any children at this point. On the other hand, Ivanka and Jared, who took the holy vows in 2009 in New Jersey, have three kids together, namely Arabella, 11, Joseph, 8, and Theodore, 6.

Clockwise from upper left, White House adviser and first daughter Ivanka Trump, her husband Jared Kushner, children Theodore Kushner, Joseph Kushner, Arabella Kushner attend a turkey pardoning event at the Rose Garden of the White House November 20, 2018 in Washington, DC. The two turkeys, Peas and Carrots, will spend the rest of their lives in a farm after the annual Thanksgiving presidential tradition today.
Clockwise from upper left, White House adviser and first daughter Ivanka Trump, her husband Jared Kushner, children Theodore Kushner, Joseph Kushner, and Arabella Kushner attend a turkey pardoning event at the Rose Garden of the White House November 20, 2018, in Washington, DC (Photo by Alex Wong/Getty Images)

Net worth

According to CelebrityNetWorth, Tiffany Trump has an estimated net worth of $10 million. On the other hand, Ivanka, with multiple ventures over the years, has accrued an estimated net worth of $300 million.

Thoughts on Dad Donald

Both Tiffany and Ivanka adore their father, regularly showering him with adulation in public. Tiffany sang his praises the night he officially became the GOP presidential nominee in 2016. “He draws out the talent and drive in people so that they can achieve their full potential,” she gushed at the Republican National Convention.”That’s a great quality to have in a father. And better yet, in the President of the United States.” She said Trump’s “desire for excellence is contagious,” and that “he’s always helped me be the best version of myself.” Tiffany also lauded his abilities as a father, recalling an incident when she lost someone close to her. “And the first call I got, as I knew I would, came from my father," she said, adding, “In person, my father is so friendly, so considerate, so funny and so real."

U.S. President Donald Trump acknowledges the audience after taking the oath of office as his wife Melania (L) and daughter Tiffany watch during inauguration ceremonies swearing in Trump as the 45th president of the United States on the West front of the U.S. Capitol in Washington, DC. January 20, 2017.
U.S. President Donald Trump acknowledges the audience after taking the oath of office as his wife Melania (L) and daughter Tiffany watch during inauguration ceremonies swearing in Trump as the 45th president of the United States on the West front of the U.S. Capitol in Washington, DC. January 20, 2017. (Photo by Jim Bourg - Pool/Getty Images)

Ivanka, who devoted four years to her father's administration, gushed about him at the 2020 Republican National Convention. "Four years ago, I introduced you to a builder, an entrepreneur, an outsider, and the people's nominee for president of the United States," she said. "Tonight, I stand before you as the proud daughter of the people's president. He is our commander-in-chief, champion of the American worker, defender of common sense, and our voice for the forgotten men and women of this country—he is our president, and my father, Donald J Trump,” she told the crowd on the South Lawn of the White House. 

Republican Presidential Candidate Donald Trump visits his Scottish golf course Turnberry with his children Ivanka Trump and Eric Trump on July 30, 2015 in Ayr, Scotland. Donald Trump answered questions from the media at a press conference.
Republican Presidential Candidate Donald Trump visits his Scottish golf course Turnberry with his children Ivanka Trump and Eric Trump on July 30, 2015, in Ayr, Scotland. Donald Trump answered questions from the media at a press conference. (Photo by Jeff J Mitchell/Getty Images)

In an 18-minute address, Ivanka reminisced about her time at the Trump White House and referenced a number of “moments I wish every American could see,” describing her dad as “a president who’s fighting for you every day from dawn ’til midnight.” 

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