Wednesday’s ceremony in the East Room marks a rare occasion for a celebration among two presidential administrations inside 1600 Pennsylvania Avenue, where President Joe Biden and first lady Jill Biden are expected to convene a who’s who of administration officials past and present — from the unique vantage point of having served in both.
It was in the same room Obama awarded Biden a surprise Presidential Medal of Freedom in 2017, a teary ceremony that reflected the two men’s deep mutual respect. While both like to play up their relationship in public, there are limits to their friendship, officials have said.
Stewart McLaurin, the president of the White House Historical Association, told CNN that the Covid-19 pandemic played a factor in the timing of the unveiling. The WHHA, a nonprofit organization, facilitates and funds the creation of the portraits.
“Covid impacted us two-and-a-half years ago, and I do think it’s important for these (portraits) to be revealed at a time when the public does have access to the White House and they can be seen,” McLaurin said.
While there’s no hard-and-fast rule for when a White House portrait ought to be unveiled, ceremonies have often been hosted by a former president’s immediate successor. And when in office, President Donald Trump never held a ceremony for the Obama portraits.
What will the Obama portraits look like?
Details about the pieces being unveiled on Wednesday are a tightly held secret, with artists and art movers signing confidentiality agreements to keep things under wraps before the big day. But the Obamas have often used art as a tool to express their tastes, so it should come as no surprise that their White House portraits are expected to do the same.
“There’s going to be a somewhat of an evolution in these portraits over time … and I think it’s actually going to be exciting,” McLaurin said in a preview of the upcoming Obama portraits. “I think this is going to be somewhat of a magical moment. I think it’s going to be an evolution of art.”
He continued, “We’re now in the heading towards the first third of the 21st century. And I think in the mind’s eye of most Americans, we see presidential portraits as these very traditional, 19th-century-looking-and-feeling portraits. But art and taste in art evolves and changes.”
While living at 1600 Pennsylvania Avenue, the Obamas opted to highlight several contemporary and modern artists.
Amy Sherald, who painted the first lady’s Smithsonian portrait, challenges conventions about race by depicting her figures’ skin in shades of gray. Kehinde Wiley, who painted the former President, re-imagines Old Master paintings with Black subjects.
Traditionally, the two latest sets of presidential portraits are placed in the Cross Hall of the White House — though Trump chose to move portraits of Bush and Clinton into a storage room after feuding with both families.
Biden moved the Bush portraits and Clinton portraits back to the Cross Hall, but with a new Obama portrait, Clinton may have to be relocated soon.
Wednesday’s ceremony at the White House
The Obamas’ return to the White House marks a rare moment for the current and past administrations to converge and look back on a presidential legacy.
Unlike the 2012 unveiling, Wednesday’s event will mostly host attendees from the same party — with some attendees having connections to both administrations.
The Obamas will be joined by family, friends, former Cabinet members and top staffers from the administration during the unveiling.
Marian Robinson, the mother of Michelle Obama who lived in the White House residence during their presidency, is planning to attend the ceremony, an Obama aide tells CNN, but daughters Malia and Sasha are not scheduled to join their parents.
Other expected attendees include Obama’s former chief of staff (and the current US Ambassador to Japan) Rahm Emanuel, former senior adviser David Axelrod, former Treasury Secretaries Jack Lew and Timothy Geithner, former Health and Human Services Secretary Kathleen Sebelius, former Attorney General Eric Holder, former Education Secretary Arne Duncan, former Director of the US Office of Management and Budget Shaun Donovan, and former White House press secretary Josh Earnest.
Biden and Obama forged a close relationship when serving in office together, but their friendship has its limits. While they speak occasionally, they are not in daily or weekly contact, people familiar with the matter have said.
After two terms working in Obama’s shadow, Biden has, at moments, differentiated himself from his predecessor. Officials have said there is also a degree of competition between the two men.
Their history, while one of partnership, has also been colored by various slights, real or perceived, that still linger.
Obama declined to endorse Biden over other Democrats in the 2020 primary, a step both men insisted was necessary to allow a true contest within the party. Four years earlier, Obama had viewed Hillary Clinton as his Democratic successor instead of Biden, who decided not to run as he grappled with his son’s death.
White House press secretary Karine Jean-Pierre said the unveiling would mark a lasting symbol of “the power of hope and change” in the White House.
Jean-Pierre highlighted the close relationship between the two presidents, saying, “Over the course of their eight years together in office, a close partnership between the two men grew through the highs and lows of the job and of life.”
Trump portraits are up next
The White House Historical Association is in the “beginning stages” of the portrait processes for former President Trump and former first lady Melania Trump, McLaurin said.
“There’s focus on specific artists that will likely be doing their portraits,” McLaurin added.
A source familiar with the situation told CNN that chatter about the portraits started in the last six months at Mar-a-Lago — Trump’s Florida residence — and that the former president recently sat for photographs. However, it’s not clear whether Trump has posed for the White House portrait artist or for photographs specifically for the portraits.
On Tuesday, Jean-Pierre declined to say whether Biden would extend an invitation to Trump should his portrait be completed during the Biden administration.
Trump’s political action committee donated $650,000 to the Smithsonian Institution in July to help underwrite the portraits of the Trumps, according to Linda St. Thomas, chief spokesperson for the Smithsonian.
The donation from Trump’s Save America leadership PAC marks the first time that funds have come from a political action committee since the institution began raising private funds for presidential portraits — a practice that started with the portraits associated with former President George H. W. Bush, St. Thomas said.
St. Thomas said another private donation of $100,000 also is helping to pay costs associated with the portraits. The funds, totaling $750,000, will go to artists’ fees, shipping, framing, installation and events.
CNN’s Fredreka Schouten, Gabby Orr, Betsy Klein and Jeff Zeleny contributed to this report.