President Donald Trump is weighing an ambitious new wave of clemency that could see as many as 250 pardons issued either on his own birthday — Flag Day, June 14 — or as part of the nation’s July 4 celebration marking America’s 250th birthday, according to a new report from the Wall Street Journal.

The proposal, still in what administration officials describe as “preliminary discussions,” would dramatically expand Trump’s already aggressive use of presidential pardon powers during his second term and further cement clemency as one of the defining features of his presidency.

According to the report, White House officials are debating whether the pardons should coincide with Trump’s birthday celebration on June 14 — which also falls on Flag Day — or whether they should instead be tied directly to the nation’s semiquincentennial festivities on the Fourth of July.

Some aides inside the White House are reportedly uneasy about the timing, warning that another major round of pardons ahead of the midterm elections could create political headaches for Republicans. Still, administration officials stressed that no final decision has been made and that Trump remains the ultimate authority on clemency matters.

The possible move would fit neatly into Trump’s broader effort to put his personal stamp on America’s 250th birthday celebration. Since returning to office, Trump has championed a series of patriotic projects tied to the anniversary, including plans for a “National Garden of American Heroes” featuring 250 statues of iconic Americans such as George Washington, Ronald Reagan, and Jackie Robinson. He has also promoted “Patriot Games” athletic competitions for high school students and ordered renovations around national monuments in Washington.

Historically, rulers and political leaders often used “jubilee” celebrations to grant mercy or forgiveness, a tradition Trump allies have increasingly referenced as justification for a broader use of presidential clemency powers.

One of the administration officials helping oversee the current pardon operation is Trump-appointed pardon attorney Ed Martin, who earlier this year argued that pardons are an “essential” part of justice and pointed to historical examples of kings and popes granting mass clemency during anniversary celebrations.

Trump’s second term has already featured some of the most controversial and sweeping pardons in modern presidential history.

Most notably, Trump issued a broad pardon for many supporters charged in connection with the January 6 Capitol riot, a move that sparked outrage from Democrats and some Republicans alike. Critics accused Trump of rewarding political allies, while supporters argued he was correcting what they viewed as politically motivated prosecutions.

Trump has also pardoned several high-profile figures tied to the cryptocurrency world and corporate fraud cases. Those granted clemency include former Binance CEO Changpeng Zhao and Silk Road founder Ross Ulbricht, whose case became a rallying point for libertarian activists and parts of the crypto community.

In another controversial case, Trump pardoned former Nikola executive Trevor Milton after Milton was convicted of defrauding investors.

The administration’s willingness to entertain high-profile pardon requests has also fueled a surge in clemency applications nationwide. The Journal reported that more than 16,000 pardon requests were filed last year — the highest number recorded since at least 1937.

Among those publicly seeking relief from Trump is disgraced FTX founder Sam Bankman-Fried, though Trump has publicly mocked the idea of pardoning him.

There has also been speculation surrounding imprisoned Epstein associate Ghislaine Maxwell after her legal team floated the possibility of cooperation in exchange for clemency. So far, however, there is no indication Trump is considering such a move. Earlier releases tied to the Epstein investigation showed Trump praising Florida investigators for pursuing Jeffrey Epstein and describing Maxwell as “evil.”

The looming possibility of another massive clemency push also revives comparisons to former President Joe Biden, who faced bipartisan criticism after commuting the sentences of nearly 2,500 federal inmates during the final stretch of his presidency. Biden’s pardon of his son, Hunter Biden, and his commutation of dozens of federal death row inmates generated particularly fierce backlash.

Trump allies argue that Biden normalized expansive uses of executive clemency, opening the door for Trump to exercise the same authority even more aggressively during his second term.

For now, administration officials say discussions remain fluid. But if Trump ultimately moves forward, the pardons would likely become one of the most politically explosive moments of the country’s 250th anniversary celebration — while simultaneously reinforcing Trump’s longstanding view that the presidency’s pardon power should be used far more aggressively than previous administrations were willing to do.