The two have discussed the possibility of one of Wynn's companies opening a hotel at 666 Fifth Avenue in New York City -- a building that was supposed to be the Kushners' trophy property but has turned out to be a costly miscalculation.
Wynn's company's involvement in the project could provide a much-needed boost for Kushner Companies, which has been floundering in efforts to finance a lofty redevelopment plan for the building.
The status of discussions between Wynn and Kushner Companies is unclear. But a deal between the two for a standalone hotel in New York City would be unusual for Wynn because his company has never developed or branded a project without a casino attached to it.
Spokespeople for both Wynn and Kushner Companies declined to comment about the discussions.
Jared Kushner stepped down as CEO of Kushner Companies to avoid conflicts of interest while working in the White House as an adviser to his father-in-law President Donald Trump. Laurent Morali runs Kushner Companies on a day-to-day basis as the company's president but Charles Kushner, Jared's father, makes major decisions, according to real estate industry executives who have done business with the company. Jared's sister Nicole Meyer also works at the firm.
According to financial analysts, the Kushners severely miscalculated when they paid $1.8 billion for the building in 2007 and now face a big challenge. Today, the office tower shoulders more than $1.4 billion in debt, according to a March report by Vornado Realty Trust, which joined as a partner on the property in 2011. The loan comes due in early 2019. Kushner Companies has various options, including securing new partners, to avoid default or losing its remaining 50% ownership stake in the building, according to people familiar with the deal. The Kushners owned all the retail and office space when they bought the tower, but sold parts of it over time to make debt payments and extend the loan due date.
A spokesman for the company said that Kushner Companies is and will remain current on its debt payments as it engages in discussions about how to reposition the building before February 2019, when its loans are due.
The discussions did not include Wynn's company providing financing for the hotel project, according to a person familiar with the talks. That means the Kushners would have to find the money elsewhere.
Wynn is a highly-respected hotelier and a top political donor who became Republican National Committee Finance Chairman in January.
But even a high-profile name such as Wynn's may not be enough to attract deep pocketed investors to the project because there's a glut of New York City hotel developments, according to Ben Carlos Thypin, co-founder of Quantierra, a quantitative real estate investment platform.
Oversupply in the city coupled with issues related to the property itself could make this a tough sell to lenders or partners.
"Even if the brand or developer is the best of the best, it's not going to change the economics of the situation," Thypin said.
Thypin said data from Real Capital Analytics, a real estate database, showed the average value of Manhattan hotel rooms has decreased by more than a third since fall 2015.
Even still, a Fifth Avenue hotel might be attractive to some partners, said Hans Nordby, managing director of CoStar Portfolio Strategy, which advises developers.
Though Nordby forecasts a dip in the city's hotel occupancy rate over the short term, he says that shouldn't scare off investors with a 20-year time horizon.
Kushner Companies has been pitching investors on an ambitious proposal to transform the 41-story office building with retail shops into a complex that would house a shopping mall, luxury condominiums and a 94-room hotel that would have occupied 11 floors. After completion, the property could be worth as much as $12 billion, according to estimates Kushner Companies presented potential partners. But negotiations for that deal fell through earlier this year.
Wynn, an outspoken businessman who has previously supported Democrats, became the RNC's finance chairman in January after serving as finance vice chair for Trump's inaugural committee. Wynn's company Wynn Resorts donated $729,000 worth of entertainment to the committee, according to filings with the Federal Election Commission.
"I look forward to helping President Trump and his Administration make America greater again for the people who work hard every day," Wynn said in a news release after being tapped for the RNC post.
FEC filings show Wynn has donated to a range of candidates and political groups. In the 2016 federal election cycle, Wynn contributed more than $1 million to mostly Republican candidates and committees, including the presidential campaigns of Texas Sen. Ted Cruz and former Florida Gov. Jeb Bush. He also gave $2,700 to Hillary Clinton's presidential campaign.
There are no records of any personal contributions from Wynn to Trump's campaign.
In an August 2016 interview with CNN, Wynn described both Trump and Clinton as friends but said he hadn't decided whom he would vote for because he was waiting for "someone to have a responsible conversation."
Wynn's relationship with Trump has been complicated. The two moguls feuded in the 1980s and 1990s over casino developments. Trump once told New York Magazine that he thought Wynn was "disturbed." And Wynn told The Wall Street Journal in 1996 that he thought Trump was "incompetent."
Wynn runs an international gambling empire. His company's assets include the Wynn casino and hotel in Las Vegas as well as resorts in the Chinese territory of Macau, where gambling is legal.