Donald Trump: Filmmaker Ian Halperin says he’ll cover $355m penalties if former President wins tennis match

Donald Trump has been gathering even more attention than usual over the past few months as he faces several legal challenges. The costliest of these to date, his New York trial that saw him accused of inflating his worth to dupe investors, came to a head on Friday 16 February. Judge Arthur Engoron slapped Trump and his two eldest sons with a ban: the former is not allowed to do business in New York for three years while Donald Trump Jr. and Eric are blocked for two. On top of this, Trump was ordered to pay a whopping $355 million in penalties.

Now, an unexpected celebrity has stepped forward with an improbably challenge for the former POTUS: a tennis match with a twist that could save Trump a whole lot of money. Here’s everything you need to know

Trump challenges to a tennis match

It is no secret that these legal costs, unless Friday’s decision is successfully appealed, will have a massive impact on the former President. His company, the Trump Organization, is already facing instability given that neither he nor his sons are allowed to be at the helm. On top of that, even for a rich man like Trump, $355 million is a lot of money - and his legal debts are reportedly growing by £70,000 a day.

One celebrity, the award-winning filmmaker Ian Halperin, has clearly seen an opportunity in this situation. He has challenged Trump - who is, of course, running again against President Biden - to a tennis match. Here’s the juicy bit: Halperin insists that he will foot Trump’s legal bills if he manages to win the game.

Halperin seems serious

Halperin’s suggestion is a serious one; he insists that he has multiple investors who have agreed to pay Trump’s legal fees if he wins the game. The filmmaker added that there’s a main investor who is happy to confirm his participation:

A billionaire stepped up and said he'll pay Trumps fine if he beats me in the tennis match. And he means it.

The idea apparently comes out a desire to put to rest the ongoing discussions about Trump and Biden’s advanced age. Both parties are in their 70s and have faced concerns that they are unfit to be in office. Halperin says the match would be televised, and therefore give Trump a chance to quash any fears he is too old to run the country. The filmmaker said:

Trump can be funny. The same can't be said for Biden.

He seemed to have really planned it out: he’s even suggested they use Trump’s tennis courts at either Mar-a-Lago or The Breakers resort in Palm Beach. Halperin has also suggested both he and Trump don the former President’s recently released golden tennis shoes for the match.

Who is Ian Halperin?

Halperin is quite the figure: he is a bestselling author and award-winning filmmaker, and he is known for his love of a good dare with a financial twist. The filmmaker, who directed and acted in the new comedy film Don’t F With Pablo, said he’ll even play the match in his costume if Trump accepts. He plays Pablo Escobar’s illegitimate Jewish son Pablito.

This is not the first time that the filmmaker has approached a celebrity with a financially backed challenge. In August 2021, he offered Prince Andrew $100 Million to carry out a lie detector test. He challenged Courtney Love to the same thing in a bid to get to the bottom about Kurt Cobain’s early death. He said these two were ‘chickens’ for declining his offer:

But Trump is not only no spring chicken he is also not a chicken.

Halperin said the offer was sent to Trump's key representative and, like any good challenge, it has a deadline. Trump has until Friday February 23rd 4PM EST (11AM GMT) to accept.

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Sources used:

Mirror: EXCLUSIVE: Donald Trump sensationally challenged to a tennis game to settle £281million damages bill

The Guardian: Trump launches $399 gold ‘Never Surrender’ sneakers after court ruling