Billionaire philanthropist Robert Smith set out to befriend Donald Trump’s inner circle while reportedly under investigation for tax evasion, DailyMail.com can disclose.

Smith, who has been named by Forbes as the richest black man in the country, went viral last year when he pledged to pay off $34 million of student loans for 400 students at an Atlanta university, prompting praise from Jamie Foxx and Martin Luther King Jr.’s daughter Bernice.

But in August it was revealed that the 57-year-old IT mogul is under investigation in a years-long case over alleged evasion of as much as $200 million in taxes.

According to Bloomberg, investigators are examining whether Smith failed to pay taxes on vast sums in offshore accounts in Bermuda, Nevis, the British Virgin Islands, the Cayman Islands and Belize.

And DailyMail.com can now reveal that while the IRS reportedly closed in on Smith this year, he befriended Trump’s daughter Ivanka – who called him a ‘great champion’ – Treasury Secretary Steve Mnuchin – who oversees the IRS – and Van Jones, a CNN host close to Jared Kushner and other White House insiders.

The billionaire held daily calls with Mnuchin during the roll out of the first coronavirus stimulus package in May and June, joined Ivanka’s White House advisory board on jobs last month and is even believed to have rented a home in Palm Beach, Florida, close to the Trump family’s playground of Mar-a-Lago.

Billionaire philanthropist Robert Smith set out to befriend Donald Trump's inner circle while reportedly under investigation for tax evasion, DailyMail.com can disclose. And DailyMail.com can now reveal that while the IRS reportedly closed in on Smith this year, he befriended Trump's daughter Ivanka - who called him a 'great champion'

Billionaire philanthropist Robert Smith set out to befriend Donald Trump’s inner circle while reportedly under investigation for tax evasion, DailyMail.com can disclose. And DailyMail.com can now reveal that while the IRS reportedly closed in on Smith this year, he befriended Trump’s daughter Ivanka – who called him a ‘great champion’

A month after Bloomberg revealed the alleged $200 million IRS probe, a September 23 White House press release announced that Smith was joining Ivanka on the American Workforce Policy Advisory Board, a government task force to rejuvenate the jobs market. He attended remotely as Ivanka welcomed him by saying: ‘Robert has been a great champion for improving access to capital in distressed communities. Incredible supporter of the administration’s actions on HBCUs’ 

The billionaire caused a media sensation when he used his commencement speech to tell 400 students in the Atlanta-based university Morehouse College class of 2019 he would pay off $34 million of their student debt

The billionaire caused a media sensation when he used his commencement speech to tell 400 students in the Atlanta-based university Morehouse College class of 2019 he would pay off $34 million of their student debt

Graduates react after hearing billionaire technology investor and philanthropist Smith say he will provide grants to wipe out the student debt of the entire 2019 graduating class in May

Graduates react after hearing billionaire technology investor and philanthropist Smith say he will provide grants to wipe out the student debt of the entire 2019 graduating class in May 

Smith had already been just one step removed from the Trump family since 2015, when he married his second wife, 35-year-old former Playboy Playmate Hope Dworaczyk, who starred as a contestant on Celebrity Apprentice alongside Ivanka in 2011. 

The billionaire’s first wife, Suzanne, filed for divorce in 2013 after 25 years of marriage, citing adultery.

Smith’s close association with the Trumps has raised eyebrows, but a source with knowledge of his activities said he had never discussed the tax evasion investigation with the first family or those close to them. 

The source added that Smith has a close relationship with senior politicians on both sides of the aisle, including Senate Minority Leader Chuck Schumer and House Speaker Nancy Pelosi.

Smith became embroiled in the alleged tax evasion probe in 2014 after federal investigators obtained financial disclosures from his divorce case, a source close to the case told DailyMail.com.

The tech investor had previously kept a low profile while he amassed billions of dollars. But the same year that investigators allegedly obtained his financial documents, Smith began a media and political blitz and a gift-giving spree that has not ceased.

A source close to Smith claimed the tax evasion probe was focused on Smith’s associate, Texas billionaire Robert Brockman – who has also not been charged.

Smith, who is based in Los Angeles, and worth $5.2 billion according to Forbes, had previously kept a low public profile. His company website did not even include his picture and he had eschewed media attention.

Smith had already been just one step removed from the Trump family since 2015, when he married his second wife, Hope Dworaczyk, who starred as a contestant on Celebrity Apprentice alongside Ivanka

Smith had already been just one step removed from the Trump family since 2015, when he married his second wife, Hope Dworaczyk, who starred as a contestant on Celebrity Apprentice alongside Ivanka

Smith's second wife Dworaczyk is a former Playboy Playmate (pictured)

Smith’s second wife Dworaczyk is a former Playboy Playmate (pictured) 

Dworaczyk (far left) also starred as a contestant on Celebrity Apprentice alongside Ivanka in 2011

After he gave the Smithsonian’s National Museum of African American History and Culture a $20 million gift in 2016, the museum’s director of development Adrienne Brooks told the Washington Post he had been a relative unknown just three years earlier.

‘We kept wondering, ‘Who is this Robert Smith?’ she told the paper.

As the federal investigation gained steam, Smith appeared on the cover of Forbes in 2015 and 2018. In 2020 alone he has made the covers of three magazines – Lifestyles, Savoy, and Town & Country.

He became the first black man to sign the Giving Pledge in 2017, committing to devoting half of his net worth to causes which support ‘equality of opportunity for African Americans’ and ecological protection.

Smith grabbed headlines in February last year when he gave $5 million to criminal justice nonprofit Reform Alliance, of which he is listed as a ‘founding partner’.

The organization’s CEO, Van Jones, has been a liberal darling, serving as a green energy jobs adviser in the Obama administration and a CNN host.

But Jones had developed close ties with the Trump administration, criticizing Hillary Clinton supporters and even working with Jared Kushner. 

He was embroiled in controversy in June over claims he worked on Trump’s police reform policies, which were slammed by Democrats, the NAACP and other civil rights organizations, the Daily Beast reported.

Smith grabbed headlines in February last year when he gave $5 million to criminal justice nonprofit Reform Alliance, of which he is listed as a 'founding partner'. The organization's CEO, Van Jones (pictured), has been a liberal darling, serving as a green energy jobs adviser in the Obama administration and a CNN host. Jones is also a friend of Jared Kushner's

The billionaire also set up daily calls with Treasury Secretary Steve Mnuchin (pictured)- who oversees the IRS - during the roll out of the first coronavirus stimulus package in May and June

Smith grabbed headlines in February last year when he gave $5 million to criminal justice nonprofit Reform Alliance, of which he is listed as a ‘founding partner’. The organization’s CEO, Van Jones (left), has been a liberal darling, serving as a green energy jobs adviser in the Obama administration and a CNN host. Jones is also a friend of Jared Kushner’s. The billionaire also set up daily calls with Treasury Secretary Steve Mnuchin (right)- who oversees the IRS – during the roll out of the first coronavirus stimulus package in May and June

But Jones had developed close ties with the Trump administration, criticizing Hillary Clinton supporters and even working with Jared Kushner. He was embroiled in controversy in June over claims he worked on Trump's police reform policies, which were slammed by Democrats, the NAACP and other civil rights organizations, the Daily Beast reported

But Jones had developed close ties with the Trump administration, criticizing Hillary Clinton supporters and even working with Jared Kushner. He was embroiled in controversy in June over claims he worked on Trump’s police reform policies, which were slammed by Democrats, the NAACP and other civil rights organizations, the Daily Beast reported

Jones denied the story’s claims, tweeting: ‘I have never been included in any meetings about police reform (not by phone, zoom, nada). I didn’t know what was in the EO [Executive Order] until the day it was released.’

Smith’s multi-million dollar donation to Jones’ nonprofit earned him glowing praise from the CNN contributor, who tweeted in May last year that ‘Robert Smith is the MAN!’ and said he was ‘fighting for criminal justice reform… He is like a real-life Tony Stark — using his genius and wealth for good.’

The billionaire caused a media sensation when he used his commencement speech to tell 400 students in the Atlanta-based university Morehouse College class of 2019 he would pay off $34 million of their student debt.

After establishing himself as a major player in the nonprofit world, the IT mogul waged a highly effective political charm offensive.

His private jet was pictured on February 3 and 4 this year at West Palm Beach airport and the billionaire was rumored to have rented a property near Donald Trump’s Mar-a-Lago club.

The president’s daughter, Ivanka, told the Washington Post that she was ‘blown away’ by Smith’s student debt jubilee, and when the coronavirus pandemic hit the US, the two began weekly phone conversations, sometimes talking multiple times a week.

The Los Angeles-based philanthropist, worth $5.2 billion according to Forbes, had previously kept a low public profile. His company website did not even include his picture and he had eschewed media attention

The Los Angeles-based philanthropist, worth $5.2 billion according to Forbes, had previously kept a low public profile. His company website did not even include his picture and he had eschewed media attention

The Los Angeles-based philanthropist, worth $5.2 billion according to Forbes, had previously kept a low public profile. His company website did not even include his picture and he had eschewed media attention

His private jet was pictured on February 3 and 4 this year at West Palm Beach airport and the billionaire was rumored to have rented a property near Donald Trump's Mar-a-Lago club (pictured)

His private jet was pictured on February 3 and 4 this year at West Palm Beach airport and the billionaire was rumored to have rented a property near Donald Trump’s Mar-a-Lago club (pictured)  

On May 10 he appeared on NBC’s Meet The Press and told interviewer Chuck Todd he wanted to praised ‘leadership in Washington, people like Ivanka Trump and Senator [sic] Mnuchin, who have been very engaged’ in African-American communities.

He claimed Ivanka and others were ‘making great progress’ in getting PPP assistance to marginalized areas.

Ivanka tweeted: ‘Robert, you are a change maker and it’s been a pleasure working with you.’

A month later she tweeted the Post article and in response, Smith wrote: ‘Thank you @IvankaTrump, @stevenmnuchin1, @senschumer for your leadership.’

Ivanka continued to heap praise on the billionaire philanthropist even after reports emerged he was under investigation in a groundbreaking tax evasion case.

One month after Bloomberg revealed the alleged $200 million IRS probe, a September 23 White House press release announced that Smith was joining Ivanka on the American Workforce Policy Advisory Board, a government task force to rejuvenate the jobs market.

Smith attended remotely as Ivanka claimed that ‘the great American comeback was under way’ and that ‘we continue to turn the corner on the virus.’ Days later the White House became the ground zero for the worst superspreader event in Washington D.C.

‘Robert is joining us virtually, hi Robert,’ she said as she led a round of applause.

‘Robert has been a great champion for improving access to capital in distressed communities. Incredible supporter of the administration’s actions on HBCUs.

‘Robert your voice will be a great addition to the board going forward.’  

Smith’s charm offensive reached Mnuchin too, who knew the billionaire from his previous career in finance.

The president's daughter, Ivanka, told the Washington Post that she was 'blown away' by Smith's student debt jubilee, and when the coronavirus pandemic hit the US, the two began weekly phone conversations, sometimes talking multiple times a week. In May Ivanka tweeted: 'Robert, you are a change maker and it's been a pleasure working with you' (picttured)

The president’s daughter, Ivanka, told the Washington Post that she was ‘blown away’ by Smith’s student debt jubilee, and when the coronavirus pandemic hit the US, the two began weekly phone conversations, sometimes talking multiple times a week. In May Ivanka tweeted: ‘Robert, you are a change maker and it’s been a pleasure working with you’ (picttured)

As racial tensions rose and the American economy crashed in May and June, the two worked closely on a program to get black-owned small businesses access to lifeline loans. 

‘At one point, we were having daily conference calls with him and his team. They gave us feedback and we made changes,’ Mnuchin told the Post in June.

‘He made a real effort and didn’t have a particular agenda… He was legitimately interested in helping the program.’

Smith has not been charged over any IRS probes – but if the Department of Justice does take action, the case could become the largest tax evasion prosecution in decades.

The most recent tax evasion case of comparable size was against Beanie Babies tycoon Ty Warner, who pleaded guilty to evading almost $6 million in taxes on $107 million held in offshore accounts.

Warner’s plea deal got him just five years probation and no jail time, with the judge praising the billionaire for his charitable giving as he handed down the lenient sentence.

Bloomberg reported that Smith has hired one of Warner’s lawyers and is seeking a settlement with the IRS to avoid criminal charges.



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