The Best And Worst Days Of Ivanka Trump’s Life

Over the last several years, Ivanka Trump has gone from heiress to entrepreneur to first daughter. During father Donald Trump’s presidency, she became a highly publicized figure, though she’s always had some degree of fame. From the reports of her extravagant wedding to Jared Kushner to the birth of her three children, many of Ivanka Trump’s happiest days have been covered by various media outlets. 

But with the Trump family comes controversy, and Ivanka Trump was not without her own controversies regarding her business, her products, and even her opinions. With a life as interesting as Ivanka Trump’s you’re bound to have some bad days, after all, but for someone in the media, bad days can be bad for business and reputation. Yikes. Read on how to find out what were some of the best days in Ivanka Trump’s life and the days she probably wished hadn’t ever happened at all.

Best: When Ivanka Trump received major business cred for this move

Ivanka Trump comes from a line of business-savvy people, so it must have been a great day when she was able to negotiate the price for the Trump National Doral Miami, “a $1 billion property that she scooped up for $150 million,” as noted by Business Insider. Ivanka’s importance in the family business was noted by her brother Eric Trump when he told Forbes, “She’s someone you do not want to underestimate. She can turn on the iron shield and give and take punches with everyone else.”

Her negotiation skills were put to the test in 2011, when she, with her father’s help, acted as lead negotiator for the Doral golf course. During the negotiations, Ivanka was pregnant with daughter Arabella, and right before they were finalized, she was forced to leave her week-old daughter to check out the property one more time. Five days later, she got the property. Michael Ashner, Winthrop chief executive, said of her negotiating skills, “She’s one of the smartest people I’ve worked with,” noting, “She’s articulate, she’s tough, and she is superb on due diligence and understanding the deal.”

Worst: The day that Nordstrom dropped Ivanka Trump's fashion line couldn't have been fun

Even if Ivanka Trump was allegedly aware that her products would be dropped by Nordstrom (via People), the reasons behind the decision have been much speculated about. Donald Trump’s controversies, such as the vulgar Access Hollywood tape that was leaked to the public, inspired boycotts from activists. The #GrabyourWallet campaign was a movement to boycott stores carrying Trump products, as Refinery29 reported, and Nordstrom notably made headlines for dropping Ivanka’s brand from their stores, with other fashion brands following suit. Neiman Marcus, Belk, Jet, and Gilt were among some of the companies to drop Ivanka’s clothing following the widely publicized controversy. 

But despite the protests and political controversies, a spokesperson for Nordstrom told Refinery29, “This was absolutely not political,” but instead, strictly for business reasons. Apparently sales weren’t doing so great. Still, politics was likely still a factor in performance, and either way, it wasn’t a good look for Ivanka Trump.

Best: The day Ivanka Trump got to chat with Justin Trudeau and the moment went viral

Ivanka Trump, during her time as first daughter, had a ton of influence on her father, to the point that he brought her along to some major events, with a roundtable discussion on women in business being her first foray into policy, as noted by People. It’s no surprise Donald Trump brought her along considering her stance on and passion for women’s empowerment in business. 

The day Ivanka Trump and Canadian Prime Minister Justin Trudeau were in the same room together at the White House was the same day that the internet lost it. Photos of Ivanka Trump gazing love-struck at Justin Trudeau made their rounds on Twitter, but the photos were only a part of a series of photos showing multiple women seemingly swooning for Trudeau, according to The Guardian

Regardless of the memes, Ivanka was happy to participate in the discussion of a task force called the United States Canada Council for the Advancement of Women Business Leaders-Female Entrepreneurs. “I’m honored to be here and really looking forward to hearing from each of you,” Ivanka told the group as she sat next to Trudeau and across from her father, as reported by The Guardian.

Worst: The day she had her tense interview with Cosmopolitan must have been embarrassing

The Trumps are no strangers to the press, but the day Ivanka Trump had a tense interview with Cosmopolitan must have been embarrassing, as it made for one of the most awkward Ivanka Trump moments. The interview with Prachi Gupta was set to be about her father’s new child care policy and maternity leave policy, which Ivanka had actually had a hand in crafting (via CNN), and things became tense when Gupta brought up Donald Trump’s controversial statements about women prior to the policy.

“I think that you have a lot of negativity in these questions,” Ivanka said in response to Gupta asking about the policy lacking anything for fathers or same-sex couples. She cut the interview early, apologizing and saying she “[had] to run,” but for Ivanka, the damage was already done, as Cosmopolitan released the transcript and the media coverage began. Later, Ivanka Trump tweeted at Cosmopolitan, saying, “Your readers do [and] should care about issues impacting women [and] children. Keep the focus where it belongs — advocating change.”

Best: The day Ivanka Trump met her now-husband, Jared Kushner, at a networking lunch

Ivanka Trump has been married to husband Jared Kushner for over a decade now, and they have three children together. Both were advisors while Donald Trump was in office, and the two have been called a power couple by the press. So the day Ivanka met Kushner must have been a day to remember. Donald Trump’s longtime business partner set up a networking event and actually introduced Ivanka and Kushner. “The best deal we ever made,” Ivanka told Vogue. They dated for a while, but had a minor breakup over their different religions in 2008, as Kushner grew up Modern Orthodox Jewish. 

Eventually, the two met again at an event by a mutual friend. Ivanka said of her relationship with Kushner in an interview with New York, “We’re very mellow. We go to the park. We go biking together. We go to the 2nd Avenue Deli.” Kushner even had something to say about meeting Ivanka. “We got introduced by two business colleagues — I got very, very lucky in that one,” Kushner said (via Marie Claire).

Worst: When Ivanka Trump found out about her parents' divorce

When Ivanka Trump was 8, her parents went through a public divorce and cheating scandal, as People reported. Her mother, Ivana Trump, and father, Donald Trump, divorced following the allegations that he had cheated with model and actress Marla Maples. (He and Maples married in 1993, though that didn’t last.) 

The tabloids covered the drama, but Ivanka Trump, when speaking about the divorce to People magazine, said, “We didn’t have newspapers in the house for a significant period of time and the TV wasn’t on when they weren’t there,” and so she wasn’t aware of the tabloid coverage as a young girl. Even during the divorce, her parents were cordial and kind to each other, even while tensions rose in the tabloids. When People asked Ivanka in the same interview about her relationship with Maples, she didn’t have a lot to say about Maples other than they weren’t close. And could you blame her? But her relationship with half-sister Tiffany Trump was strong. “She’s my little sister! I’ve been close to Tiffany her whole life, and I really love her,” she said in the same interview.

Best: The days Ivanka Trump gave birth to her kids must have been a dream

Ivanka Trump has three children with Jared Kushner — Arabella, Joseph, and Theodore — and the days they were born must be a highlight of her life. Arabella, the oldest, was born on July 17, 2011, and Joseph arrived on Oct. 14, 2013. Theodore, her youngest child, was born March 27, 2016, and has been a joy for Ivanka ever since. In a series of Instagram throwback photos of Theodore days after his birth, Ivanka wrote, “You bring joy to our lives each minute of every day!” It’s clear how much Ivanka loves her children, as her Instagram features them quite often enjoying quality time. 

Ivanka Trump is big into motherhood and has stated in a video for her father, “The most important job any woman can have is being a mother.” While this statement may have caused controversy, she loves being a mother and cherishes time with her children because, as she said, she doesn’t “have an enormous quantity of time to spend with them,” as reported by CNN.

Worst: It must have been really difficult after her father's vulgar recording was leaked

When Donald Trump was the 2016 Republican presidential nominee, a 2005 recording was leaked to the public, in which he was caught saying sexist and derogatory things about women. Surely this must have been difficult for Ivanka Trump, as his daughter, to hear. For a while after, she didn’t speak up on the matter. But finally, she broke her silence two weeks later to Fast Company on the same day her stepmother, Melania Trump, gave her statement to Anderson Cooper.

“My father’s comments were clearly inappropriate and offensive and I’m glad that he acknowledged this fact with an immediate apology to my family and the American people,” she said to Fast Company. Despite the fact that she clearly didn’t support her father’s comments, in the same interview, Ivanka made it clear her relationship with her father is close, alluding to the idea that he isn’t all the media makes him out to be. This isn’t surprising, as Ivanka has supported her dad in the past.

Best: When Ivanka Trump launched an initiative to empower women globally

Ivanka Trump has received praise for launching the Women’s Global Development and Prosperity Initiative, which aims to empower women financially around the globe so that they can re-invest in their communities. In Donald Trump’s 2020 budget proposal, he allotted $100 million for Ivanka’s organization, which seemed like a great step towards helping women globally. She said that the organization was “working towards our goal of economically empowering 50 million women in developing countries by 2025,” in a statement to the Associated Press

The initiative received some criticism for its timeliness, before the 2020 elections, but according to NPR, “Experts who work with women’s issues in the global development community are hopeful about the new initiative.” According to The Washington Post, Trump’s initiative received a lot of praise at a state department meeting. The publication reported that she “entered … to a standing ovation.” Likely this could be one of her most important and fulfilling moments in her political career.

Worst: The day she was accused of copying another designer's shoes

Another bad day for Ivanka Trump’s brand was when designer Aquazzura accused the first daughter of copying the design of one of their shoes in June 2016. The “Wild Thing” red sandal with fringe across the toe and at the end of the ties ran around $700, compared to Ivanka’s similarly designed heel at about $145, according to Mic. Because of the design’s distinct look that’s reportedly indicative of the brand, Aquazzura filed a trade dress infringement suit against Donald Trump’s eldest daughter, as well as Marc Fisher, her licensee. Ivanka Trump and Marc Fisher denied the allegation.

A judge mandated Ivanka testify in court, but her legal team argued that she should be excused from having to testify. She said, “I had no involvement in the conception, design, production or sale of the ‘Hettie Shoe,'” according to the Associated Press. About a year after initially suing, Aquazzura dropped the lawsuit.

Best: The day she began her career in politics as a presidential advisor

Ivanka Trump became an employee to the White House officially in late March 2017, as an unpaid adviser to her father, an expansion of her previous role as a special assistant. Though her new role did raise some ethical concerns, as she wouldn’t be officially sworn in but would have access to classified information, she answered concerns by stating (via Politico), “I will voluntarily follow all of the ethics rules placed on government employees.”

During her time as an advisor to President Donald Trump, Ivanka has focused on women empowerment in education and economics, with strategies such as her Women’s Global Initiative and her backing of the Trump Administration Industry-Recognized Apprenticeships that would help create more jobs in America. 

Still, even with her accomplishments in policy during her father’s time as president, she wasn’t sure about returning if her dad won a second term. In an interview with Face the Nation (via CNBC), she said, “I am driven first and foremost by my kids and their happiness, so that’s always going to be my top priority.” Still, we imagine the start of her time as a political advisor was an exciting day for her.

Worst: When Ivanka Trump's 2017 book received less-than-stellar reviews

It’s not easy to write a book, but Ivanka Trump’s done it. Women Who Work was released in 2017, and is a call to action to other women on how to cultivate opportunities and succeed in business. Ivanka even donated full royalties to the Ivanka M. Trump Charitable Fund, a donor-advised fund that gives grants for organizations that support women (via CNN). While the book made over $1.1 million, according to Forbes, it still ended up losing money for its publisher and garnered pretty negative reviews. Fifty-eight percent of people who reviewed it on Amazon gave it one star, as reported by Harper’s Bazaar.

Most of the criticism said that the book was a summary of other self-help books already on the market, and that Ivanka was blind to the privilege that led to her success (via Independent). Even with the scathing reviews, she put on a proud front on social media by promoting her new book. But anyone who writes knows how much those bad reviews can sting, so that day must not have been easy for her.

Best: The day Ivanka Trump got married was like a fairytale

One of Ivanka Trump’s best days was when she got married to Jared Kushner in an extravagant ceremony in 2009. She and Kushner, being children of wealthy parents and entrepreneurs in their own right, were able to spend some serious money to create a beautiful ceremony. The two rented out the Trump National Golf Club at around $64,000, and Ivanka’s wedding dress alone was just over $50,000, according to Express. Her dress was a stunning Vera Wang design, custom-made for her with Chantilly and Lyon lace, and her ring was worth just over $545,000. The wedding cake was designed by the famous Sylvia Weinstock and was 13 layers and 70 inches tall. 

In an interview with Brides, Ivanka said, “I’ve always envisioned myself having a traditional and elegant wedding, even before the engagement.” She also stated in the interview, “As soon as I started walking down the aisle toward my husband, everything else just melted away.” She sure looked beautiful, and, considering the money they dropped on the wedding, it must have been a dream come true. 

Worst: When Ivanka Trump's father lost the 2020 election

The 2020 presidential race went to Joe Biden, thus ending Donald Trump’s time as president and, subsequently, Ivanka Trump’s time as first daughter. That couldn’t have been a good day for anyone in the Trump family. Ivanka even tweeted in support of her dad, writing, “Every legally cast vote should be counted. Every illegally cast vote should not. This should not be controversial.” CNN reported that she soon changed her tune, stating that she and Jared Kushner were advising that her dad to concede the election. “She also knows that her entire future — now more than ever — is tied to her father’s,” an insider told CNN. Ivanka has also responded to the claims of investigations against her dad for tax fraud in a series of heated tweets, according to Vanity Fair

Donald Trump’s controversial term as president has affected a lot of people’s views about him and his family as well, which leaves Ivanka Trump needing a new strategy for her brand now that she isn’t first daughter. The Guardian reported she will likely not return to fashion, as she closed her brand to focus on her job in the White House.

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