Inside Ivanka's Relationship With Her In-Laws

When Donald Trump assumed the presidency in January 2017, all eyes were on him and his family, as his approach to the office was littered with his children and in-laws. Unlike presidents of the past, who relied on mainly campaign managers and political experts to guide them throughout the presidency, Donald sought advice largely from his eldest daughter, Ivanka Trump, and his son-in-law, Jared Kushner — putting Jared, for example, in charge of settling tensions in the Middle East. The move was shocking to some, the lengths Donald went to enabling Ivanka's security clearance were startling to others, and his entire approach struck many as incestuous (per Vanity Fair).

Given how close Ivanka and Jared were to the Oval Office, some safely assumed the married couple were closest to Ivanka's family — her father, brothers, and the then-president himself. But, as it turns out, Ivanka and her husband may be more emotionally tied to the Kushner in-laws, especially now that the Trump family is out of Washington, D.C., and back in Florida. Given the changing dynamic and their ever-present standing in the headlines, we did some digging to take a close look at Ivanka's relationship with her in-laws.

Before we jump into Ivanka Trump's complicated relationship with her in-laws, we should first establish just how similar her own family is to the Kushner family. Donald Trump got his start in the New York real estate business, making a name for himself as an insanely wealthy and powerful man with a chokehold on the city's living and infrastructure. However, as noted by New York Magazine, Jared Kushner comes from extremely similar circumstances, as his father, Charles Kushner, was also a New York real estate tycoon.

Unlike Donald, who used his power to intimidate people into doing his bidding, Charles reportedly used his charm. As New Jersey's top real estate mogul, Charles built a $2 billion empire and used his "Jewish Kennedy" suaveness to get him there. "Charlie's good points are incredibly good," a former employee said of the Kushner patriarch. "But if you cross him he becomes maniacal. He will crush you," noted New York Magazine. Charles himself wrote an opinion column for The Washington Post about his career, boasting that his success in sports, insurance, banking, and energy also contributed to his family's influence. It's no wonder that Ivanka and Jared crossed paths.

Before they joined the White House, Ivanka Trump and Jared Kushner were well established. Their respective families ensured they had political capital and money to burn, but, of course, where there's smoke, there's fire. Their respective in-laws both conducted themselves in allegedly questionable business dealings, perhaps giving Ivanka the ability to relate to the Kushner family and vice versa. Let's start with Donald Trump. Of course, many of his scandals occurred during his run for president, but let's name a few (per The Atlantic). There's the racial housing discrimination scandal that rocked Donald's business dealings in the 1970s as well as Trump University (who could forget?). Tenant intimidation also impacted Donald's real estate practices, and, of course, there's the issue of the sexual assault allegations lodged against him.

As for the Kushner family, Charles Kushner's real estate company was found to have violated a number of laws regarding tenant disputes, and a judge ruled that the real estate mogul had charged "deceptive" fees to renters, per ProPublica. Charles was even arrested and charged with 18 counts of tax evasion in 2005, as reported by the Chicago Tribune.

Now that we've established the environments in which Ivanka Trump and Jared Kushner were raised, we can start talking about their relationship and how it blossomed. As per Vogue, Trump and Kushner met in 2007 for what was supposed to be a business lunch. A real estate broker who knew each of them individually thought they'd hit it off professionally, not realizing that they'd also set up a future married couple. "They very innocently set us up thinking that our only interest in one another would be transactional," Trump explained. "Whenever we see them we're like, 'The best deal we ever made!'"

Trump then explained to Vogue just how similar her upbringing was to Kushner's, giving us insight into why their respective in-laws would love their spouse. Both Trump and Kushner came from prominent New York real estate families, went to Ivy League universities, got their professional start at their fathers' companies, and worked extremely hard to achieve their own ambitions. If two people were seriously made for each other, it's these two. But what did Kushner's parents think of his partner?

While it seemed as though Ivanka Trump and Jared Kushner were a match made in heaven, Jared's parents were initially completely opposed to the young couple dating. In her extensive book, "Kushner, Inc. Greed. Ambition. Corruption. The Extraordinary Story of Jared Kushner and Ivanka Trump," Vicky Ward details just how "horrified" Seryl and Charlie Kushner were when Jared and Ivanka started dating. The future presidential advisor's parents were so "dismayed" that they initially refused to even meet Donald Trump's daughter.

So why did Seryl and Charlie hate Ivanka that much? As it turns out, much of their shock and horror came from Jared dating (and potentially marrying) outside the Jewish faith. "The idea was particularly offensive to Seryl, who had raised the children," Ward writes in her book. "They were her world, and her world was the closed conservative Jewish culture she had grown up in." It was only after Charlie's friend, Alan Hammer, talked the parents into meeting Ivanka that they started to loosen up (a little). "You're the closest people to your children of anybody I know," Alan told Charlie, as stated in the book. "So, what are you going to do, Charlie?"

It turns out that religion was a prominent component of Jared Kushner and Ivanka Trump's relationship, and it even resulted in a brief breakup between the two. But, as per Esquire, they quickly got back together after Ivanka decided to convert. You'd think that such a gesture to her future in-laws would've gotten Ivanka in Charlie and Seryl Kushner's good graces, but Charlie still had his doubts. Esquire reported that Charlie drilled Ivanka on all things Judaism and tested her on the faith. "This wasn't like, 'Talk to a rabbi, read a couple of paragraphs,'" an insider shared about Charlie's expectations. "It was hard and difficult, and it was on Charlie's terms."

Such a grueling experience might make you think that Ivanka has a difficult relationship with her faith, but, in her interview with Vogue, she shared just how much her practice of Judaism means to her. "It's been such a great life decision for me," she said. "I am very modern, but I'm also a very traditional person, and I think that's an interesting juxtaposition in how I was raised as well ... [Judaism] creates an amazing blueprint for family connectivity."

To say that Seryl and Charlie Kushner put Ivanka Trump through the ringer seems like an understatement. They clearly had expectations of their son's significant other, but Ivanka reportedly blew their socks off. In her book "Kushner, Inc. Greed. Ambition. Corruption. The Extraordinary Story of Jared Kushner and Ivanka Trump," Vicky Ward details just how charming Ivanka was during Charlie's grueling tests regarding religion. She "far surpassed" the Kushner patriarch's expectations, and by the time the wedding rolled around, both Seryl and Charlie were thrilled that Jared and Ivanka were tying the knot. "[Ivanka] had ... charmed Charlie, who would proudly explain to a friend that she really wanted to be a Kushner," Ward writes in her book. "They were the close family she had never had."

Jared and Ivanka got married on October 25, 2009, at the Trump National Golf Club in Bedminster, New Jersey, their wedding being a who's who of political and social circles. And, perhaps, in one of the most surprising turns of the evening, Charlie gave a toast to the couple that was "memorably, startlingly emotional."

When one of your siblings gets married, it's really easy to become close to your new sibling-in-law — chances are they're around your age and have similar values. For Ivanka Trump, she got a brother-in-law in Joshua Kushner, and when more and more information about Ivanka came to the forefront, her relationship with Josh was touched upon.

In an interview with Forbes in 2017, Josh shared that he wasn't just close with Ivanka — she was like the sibling he'd longed for, and he even referred to her as his sister rather than his sister-in-law. By all accounts, they seemed tight, but it might shock you to learn that Josh is a Democrat. "It is no secret that liberal values have guided my life and that I have supported political leaders that share similar values," he shared in the same interview. "But neither political party has a monopoly on the truth ... It's important to be open minded and learn from differing opinions."

As clearly displayed just moments ago, Josh Kushner has very different political opinions than that of Jared Kushner and his sister-in-law, Ivanka Trump. When it was his turn to tie the knot, Josh found a partner who shared equally liberal politics — supermodel Karlie Kloss — but, despite their differences, Ivanka and Jared joined the couple on their big day. As per People, Josh and Karlie's wedding featured a variety of celebrities and A-list guests, from Kendall Jenner to Gwyneth Paltrow. Of course, Ivanka was there to celebrate her new in-laws' nuptials, seemingly putting rumors of tension to bed with a heartfelt message to the couple.

Commenting on one of Karlie's posts from her big day, Ivanka wrote on Twitter, "So much love for you both as you begin forever together," alongside a heart emoji. Did the message reassure fans that all was well in wedding paradise? Not really. One commenter on Twitter replied, "I would say this is the poor version's Ivanka and Jared, but I like them more than I like you. And I don't know anything about them." So much for easing tensions.

From our digging, it seems as though Ivanka Trump tried really hard to get on Karlie Kloss' good side. Karlie is, of course, a bonafide star in her own right and clearly didn't need (or want) to ride on Ivanka's coattails to Republican fame. But, despite their differences, Ivanka still took to social media often, praising the model and her husband. "I feel blessed to have you as a sister," Ivanka once wrote on Karlie's Instagram, per Glamour. "[I] look forward to the decades of happy memories we will create together as a family!"

Did Karlie take the bait? In the earlier stages of her marriage to Josh Kushner, it appeared as though she tried to make it work. JustJared reported in 2019 that Karlie and Josh vacationed along with Ivanka and Jared Kushner in Rome, and they were all spotted on occasion strolling the city and grabbing lunch as a foursome. Karlie even accompanied Ivanka and Jared to designer Misha Nonoo's wedding while in Italy, so there was a little glimmer that the two sisters-in-law might have worked out any kinks in their relationship.

There was once a time when Jared Kushner's parents wouldn't even meet Ivanka Trump, but, as clearly proven, that attitude changed with effort on Ivanka's part and acceptance on Charlie and Seryl Kushner's side. By the time Ivanka and Jared were working in the White House, Charlie and Seryl became visitors and were even spotted at the couple's home in the swanky Kalorama neighborhood of Washington, D.C., on occasion.

On one given afternoon, Charlie and Seryl were seen arriving at Ivanka and Jared's home, even though the couple were at work. As per the Daily Mail, the Secret Service escorted the elder Kushner couple out of a gray car and into the house. With them were suitcases, toys, wine, and a case with Arabella Kushner's name — Jared and Ivanka's daughter — prompting speculation that the grandparents were getting ready for a weekend getaway with Jared, Ivanka, and their children. Certainly a far cry from their early impression of Ivanka, it became clear in just this instance that Charlie and Seryl are dedicated parents-in-law and grandparents.

Their romp to Rome in 2019 seemed to suggest that things were thawing between Ivanka Trump and Karlie Kloss, but 2021 changed everything for the sisters-in-law. January 6, 2021, marked the dangerous and tragic siege of the United States Capitol — of which Ivanka is said to have pertinent information about, per AP News – and her role on the day in question certainly seemed to mark the final straw for Karlie, who took to social media on the day to share her unfiltered thoughts on the pro-Trump attack. "Accepting the results of a legitimate democratic election is patriotic," she wrote on Twitter. "Refusing to do so and inciting violence is anti-American."

The message certainly didn't seem to attack her in-law in particular, but when a fan responded, "Tell your sister-in-law and brother-in-law," Karlie responded, "I've tried." Per Page Six, Ivanka was left feeling "surprised and hurt" by Karlie's sentiment, but sources confirmed that the two hadn't shared a "close relationship" for "quite some time" by that point. Since then, Ivanka has been relatively silent on social media, and neither has been vocal about the other.

Presidential pardons often come at the end of an administration. Sometimes pardons are afforded to those who have been wrongfully convicted (for example, Barack Obama largely used his pardon power to erase drug charges). For Donald Trump, he used his pardon power for much different purposes, and, in addition to commuting the sentences of the likes of Scooter Libby (charged with obstruction of justice) and Michael Flynn (charged with giving false statements to federal investigators), he also pardoned Jared Kushner's father, Charlie Kushner, who was charged and convicted of tax evasion and illegal campaign donations.

Former New Jersey governor Chris Christie was the U.S. attorney assigned to Charlie's case back in 2005, and he told ABC News that it was "one of the most loathsome, disgusting crimes" he ever prosecuted in his career. Charlie — who was in business with his brother-in-law at the time — allegedly hired a sex worker to lure his brother-in-law in an attempt to "intimidate" him. Why? His brother-in-law was cooperating with federal investigators. Charlie's "revenge" scheme didn't work, and he was charged. Ivanka Trump's father later pardoned her father-in-law and cited that his "record of reform and charity" outweighed his indiscretions.

When Donald Trump left Washington, D.C., his family ventured south to Florida. He and his wife, Melania Trump, have been residing at Mar-a-Lago, and Ivanka Trump and Jared Kushner followed suit. As per CNN, Ivanka and Jared signed a lease at a luxury condo in Miami, The Arte, dishing out $40,000 a month in rent. While living in the glamorous rental, Ivanka and Jared made an investment on the exclusive Indian Creek Island, where a more permanent home is being built for them.

So, why Florida? Some may think it's because most of the Trumps live there now, but, as it turns out, Jared's parents also call Florida home. Charlie and Seryl Kushner own a home in the sunshine state, per SCMP, that they use as a vacation destination. Now that their grandchildren are there, it's safe to say that Florida is the place for the Trump/Kushner gang. So, do all the family members spend time together? SCMP noted that Charlie and Seryl actually haven't been spotted with Donald, despite living a short distance away, though there may be a reason for that (keep reading!).

Given that Ivanka Trump and Jared Kushner live in Florida, just a stone's throw away from Donald Trump's residence, you'd think that the families would get together on a regular basis. However, it appears as though time has been a cruel teacher, and, as the Daily Mail noted, Ivanka, Jared, and their children spend far more time with Jared's family than the Trump counterparts. So, what happened? As per the Daily Beast, Jared and Donald had a major falling out after their time in Washington, D.C., came to an end, and it's no doubt bled into the former real estate mogul's relationship with his daughter. Jared — who was once one of Donald's most trusted advisors — wasn't even part of the team that rolled out Donald's political comeback, and multiple sources confirmed that the two do not see eye to eye.

This, however, might be good news for Charlie and Seryl Kushner, who now are spending ample time with Ivanka and Jared's children, Arabella, Joseph, and Theodore. As the Daily Mail reported, the elder Kushner couple joined Ivanka, Jared, and their kids on a stroll in Florida the same day that Donald held his first rally of 2022 in Arizona.