The Infamous $20,000 Donald Trump Portrait by Michael Israel

2008, seven years before Donald Trump ran for president, artist Michael Israel created a six-foot portrait, in just seven minutes, that would later spark global conversation—a stunning live painting of Donald Trump. What started as a heartfelt effort to support HomeSafe, a cause close to Michael’s heart, became one of the most infamous moments in the intersection of art, charity, and politics.

A Longtime Supporter of HomeSafe

For years, Michael Israel has been a dedicated advocate for HomeSafe, a Palm Beach-based charity serving over 16,000 victims of domestic violence annually. The organization provides critical support to vulnerable children and families, offering shelter, counseling, and programs to help them rebuild their lives.

Michael has used his talents to support HomeSafe on multiple occasions, donating both his time and providing art to raise funds to help the charity fulfill its mission. His live painting performances have consistently drawn in substantial funds, combining the thrill of art with the power of philanthropy.

The 2008 Mar-a-Lago Event

In 2008, Michael took the stage at a glittering charity gala at Mar-a-Lago. The event was designed to benefit HomeSafe, with all proceeds supporting its essential programs. True to form, Michael brought his trademark energy, creating five breathtaking works of art in front of a live audience.

The highlight of the evening was a bold six-foot portrait of Donald Trump, painted in just seven minutes. The audience was spellbound as Michael brought the image to life with sweeping strokes and explosive colors. Melania Trump placed the winning $20,000 bid on the portrait, selecting it as her choice from the five works Michael created that evening.

The event raised significant funds for HomeSafe, ensuring vital services for families in need. The story seemed destined for a happy ending, a shining example of art’s ability to bring communities together.

Seven Years Later: Controversy Strikes

In 2016, during Donald Trump’s presidential campaign, the painting re-entered the spotlight—not as a testament to charity, but as a source of controversy. The Washington Post questioned the Trump Foundation’s use of funds to pay HomeSafe for the painting, raising the issue of whether the piece had been retained as a personal gift.

Suddenly, a painting created to help victims of domestic violence became the subject of political scrutiny. The controversy overshadowed the event’s original purpose and shifted the focus away from HomeSafe’s mission.

Michael Israel’s Perspective

For Michael, the painting was never about politics. “I can do more with my paint and canvas than with just money,” he explains, emphasizing his dedication to using art to inspire generosity. Michael has spent decades raising funds for causes like cancer research, the Special Olympics, and of course, HomeSafe.

The media frenzy surrounding the Trump portrait disappointed Michael, as it detracted from the vital work being done by HomeSafe. He hoped the attention would eventually return to the families and children the event was meant to help.

“All of us in America could use some uplifting,” Michael reflected. “We need less fighting and more focus on what brings us together—life, liberty, and the pursuit of happiness for all.”

A Presidential Footnote

The painting even garnered a mention on the world stage. During the presidential race, President Obama jokingly referenced the Trump portrait, quipping, “At least he had the taste not to go for the 10-foot version!”

What Obama didn’t know was that Michael had also painted six-foot portraits of him at other events, including the Black Tie Blue Dominion Inaugural Ball at the Smithsonian. While Trump’s portrait sparked bidding wars and media attention, Obama’s portrait from that event remained unsold, quietly underlining the unpredictable journey of art. There is a lot more to this sage, to be revealed in other posts.

A Legacy of Charity

For Michael Israel, the Trump portrait is just one example of how art can make an impact. As a longtime supporter of HomeSafe, he has continued to create awe-inspiring live art to benefit the charity and others like it. His work transcends controversy, using its reach to inspire hope, generosity, and positive change.

The $20,000 portrait may have become infamous, but its true legacy lies in the lives it helped transform through HomeSafe’s vital programs. For Michael, that’s what matters most.