With 16 days remaining in his half-century political career, President Biden is expected to bestow one of the nation’s highest honors on Saturday to core members of the political, financial and celebrity establishment of which he has long been a part.

President-elect Donald J. Trump will replace Mr. Biden on Jan. 20 and is determined to continue his assault on what he has long called “the swamp.” In 2016, Mr. Trump vowed to wage war against establishment members of both parties who he said had “reaped the rewards of government while the people have borne the costs.”

But on Saturday, Mr. Biden will award the Presidential Medal of Freedom to 19 Americans, including some of the brightest minds of the old guard that Mr. Trump wants to topple. In doing so, the 82-year-old outgoing president is sending an unmistakable message of support for a democratic order that he believes is threatened by Mr. Trump’s re-election.

Honorees include Hillary Clinton, the former first lady, senator and secretary of state who Mr. Trump has threatened to jail; Robert F. Kennedy, the assassinated senator whose son hugged Mr. Trump; and George Romney, the late father of Senator Mitt Romney, the Utah Republican who repeatedly rejected Mr. Trump’s actions and philosophy.

Like many presidents with the Medal of Freedom, Mr. Biden will also honor some of his party’s most prolific fundraisers, including the man who is the biggest among Democratic donors – George Soros, the liberal activist billionaire whom Republicans have singled out as their evil mastermind of the party.

They include media executive and cultural figure Anna Wintour, who placed the first lady, Jill Biden, on the cover of Vogue twice in the last four years, while spurning Melania Trump during her husband’s presidency. Ms. Wintour is one of the fashion industry’s leading fundraisers and hosted events for Mr. Biden’s re-election campaign in London and Paris last year.

Mr. Biden will also recognize artists, musicians, athletes, philanthropists and others who have contributed to society, including singer Bono, actor Michael J. Fox, basketball legend Magic Johnson and investor David M. Rubenstein.

All modern presidents have awarded the medal to those they deemed worthy, often because they had finally left the political stage and sometimes with an ideological bent. Historians view it as the final use of the presidential megaphone to tell Americans, “This is who we should admire and emulate.”

After Mr. Trump won in 2016, President Barack Obama presented the medal to NBA star Michael Jordan, actors Tom Hanks and Robert De Niro and others. Mr. Obama previously gave the award to Mr. Biden, who served as his vice president.

Four years later, when Mr. Trump left office, he presented the medal to two professional golfers, an Olympic athlete and Reps. Devin Nunes of California and Jim Jordan of Ohio, two of his fiercest Republican supporters in Congress.

But Mr Biden’s use of the presidential prerogative appeared to be even more targeted than that of some of his predecessors.

His decision to posthumously award Mr. Kennedy the medal could be seen as a rebuke to Mr. Kennedy’s son, a member of perhaps the country’s most famous Democratic family. Robert F. Kennedy Jr.’s decision to support Mr. Trump during the campaign — despite denunciations from most of his relatives — contributed to Mr. Trump’s nomination of him to head the Department of Health and Human Services.

The White House noted that the elder Mr. Romney, a Republican, was chairman and president of American Motors Corporation and later served as governor of Michigan and secretary of housing and urban development. But he was also the father of the younger Mr. Romney, the only Republican to vote twice to convict Mr. Trump after his two impeachment trials.

The award for Mr. Romney mirrors Mr. Biden’s decision this week to award the Presidential Citizens Medal, one of the country’s highest civilian honors, to Rep. Liz Cheney, who led the effort to impeach Mr. Trump for his actions during the attack to hold the Capitol accountable in 2021.

Both awards from a Democratic president to prominent Republicans offered Mr. Biden the kind of public relations boost that has largely been reserved for Mr. Trump since the election.

The same cannot be said for Mr. Soros. By awarding him the medal, Mr. Biden recognizes how important the investor and philanthropist was to the Democratic Party. Many members of Mr. Biden’s party were wary of doing so, fearing that Mr. Trump and other Republicans would use it as evidence of the conspiratorial control they say he exerts.

But Mr. Biden appears willing to ignore that concern. After weeks in which Mr. Trump presented Elon Musk, the world’s richest man, as a member of his inner circle, Mr. Biden seemed to want to say: We have our billionaires too.

Mr. Soros has spent hundreds of millions of dollars on progressive policies since the Supreme Court’s Citizens United decision, which poured a flood of money into politics from corporations and the wealthy people who run them. Mr. Soros and his family provided critical support to Mr. Biden in the immediate aftermath of Mr. Biden’s disastrous debate performance last year.

The White House’s description of Mr. Soros was more reserved, focusing on his founding of the Open Society Foundation: “Through his network of foundations, Soros has supported organizations and projects around the world that strengthen democracy, human rights, education and social welfare.” Justice.”

Other major benefactors include Tim Gill, a software entrepreneur who is a major donor in the gay community and an advocate for LGBTQ rights first in his home state of Colorado and then nationwide. During the 2020 race, he donated $355,000 to the Biden Victory Fund.

Theodore Schleifer contributed to reporting.