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WASHINGTON – President Donald Trump has said he learned lessons from President Richard Nixon’s fall from grace, but in using the power of his office to keep his friend and adviser Roger Stone out of prison he has now crossed a line that even Nixon in the depths of Watergate dared not cross.

For months, some of Trump’s senior White House advisers warned him that it would be politically self-destructive if not ethically inappropriate to use his clemency power to help Stone, who was convicted of lying to protect the president. But in casting aside their counsel Friday, Trump indulged his own sense of grievance over precedent and restraint to reward an ally for his silence.

Democrats immediately condemned the commutation of Stone’s 40-month prison term and vowed to investigate, just as Trump’s advisers had predicted they would. House Speaker Nancy Pelosi, calling the move an act of “staggering corruption,” said she would pursue legislation to prevent the president from using his power to protect those convicted of a coverup on his own behalf, although that would face serious constitutional hurdles and presumably would never be signed into law by Trump.

Still, Trump’s action was too much for some GOP critics of the president, who called it an abuse of power intended to subvert justice on his own behalf. “Unprecedented, historic corruption: an American president commutes the sentence of a person convicted by a jury of lying to shield that very president,” Sen. Mitt Romney of Utah wrote on Twitter.

Trump had long publicly floated the possibility of clemency for a variety of associates caught in the cross hairs of prosecutors, including Stone, former National Security Adviser Michael Flynn and former campaign chairman Paul Manafort. That by itself was interpreted by some critics as an act of witness tampering, in effect promising intervention to allies as long as they did not cooperate with investigators against Trump.

By contrast, one former associate who did cooperate, Michael Cohen, his former lawyer who arranged to pay hush money to women claiming extramarital affairs with Trump, was locked up again on Thursday after federal authorities demanded that he agree not to publish a tell-all book in September, deeming it a violation of the terms of his early release.

While Trump has enthusiastically used his clemency power to help political allies and others with connections to his White House, he had until now deferred to advisers urging him not to use it for Stone or others caught up in investigations of the president’s campaign ties to Russia, recognizing that it would be politically explosive.

But with Stone due to report to prison in the next few days, Trump opted not to wait any longer and the commutation could be a test case for what he could do next. If he judges that the political cost was not too high, he may be emboldened to help out others, although it may not be necessary since Manafort has now been released early and Trump’s Justice Department has moved to drop the case against Flynn even though he pleaded guilty to lying to the FBI.

While most elected Republicans remained silent about Stone’s commutation, some of the president’s staunch supporters who have likewise attacked the legitimacy of the underlying investigations into Trump and his associates cheered him on.

“In my view it would be justified if President @realDonaldTrump decided to commute Roger Stone’s prison sentence,” Sen. Lindsey Graham of South Carolina, chairman of the Senate Judiciary Committee, wrote on Twitter. “Mr. Stone is in his 70s and this was a nonviolent, first-time offense.” (Stone is actually 67.)

Other presidents have also generated blowback through disputed pardons, including some involving people close to them.

Just days before the 1992 election, Lawrence Walsh, the independent counsel investigating the Iran-contra affair, filed a new indictment against former Defense Secretary Caspar Weinberger that made public notes contradicting President George H.W. Bush’s account of his involvement. Bush’s team considered that a dirty trick intended to influence the election, and indeed Bush was defeated days later.

Bush responded the next month to what he considered an illegitimate prosecution by pardoning Weinberger and five others on Christmas Eve, prompting Walsh to complain that “the Iran-contra coverup, which has continued for more than six years, has now been completed.”

His successor, President Bill Clinton, waited until the final hours of his tenure in January 2001 to issue a raft of more than 175 pardons or commutations, including for his own half brother Roger Clinton, the financier Marc Rich and several former administration officials.

Among those Clinton pardoned on his last day in office was Susan McDougal, a friend and former business partner from his Arkansas days who spent 21 months behind bars for refusing to cooperate with independent counsel Ken Starr’s investigation of the Whitewater land venture.

Unlike the case with Stone, Clinton acted only after McDougal had already served her sentence and been released. With Starr no longer in office and the Whitewater investigation shut down, Clinton faced no additional legal risk at that point.

The bigger furor at the time was over his pardon of Rich, who had fled the country to avoid charges of evading $48 million in taxes and obtained his clemency after his ex-wife, Denise Rich, a prominent Democratic donor, contributed money to Clinton’s presidential library.

Democrats joined Republicans in roundly condemning the pardon, and Clinton later expressed regret because of “the terrible politics.”

Jack Goldsmith, a Harvard Law School professor and former top Justice Department official under President George W. Bush, said those cases could be seen as parallels to Stone’s commutation but pointed to the larger pattern under Trump. In 31 of 36 pardons or commutations that he has issued, the act advanced his political goals or benefited someone he had a personal connection to, whose case had been brought to his attention by television or was someone he admired for their celebrity.

“This has happened before in a way,” Goldsmith said. “But there has been nothing like Trump from a systematic perspective.”

One president who dared not use his pardon power to help his friends was Nixon, although not for lack of thinking about it. Nixon’s associates paid hush money and dangled the prospect of executive clemency to the Watergate burglars to buy their silence, but that was off the table once the Watergate story broke open.

Likewise, Nixon secretly promised a pardon to H.R. Haldeman, his chief of staff, on the day after Senate hearings opened.

“I don’t give a shit what comes out on you or John, even that poor damn dumb John Mitchell,” he told Haldeman, in a conversation captured on his Oval Office taping system. “There is going to be a total pardon.”

But he never followed through. Haldeman, John Ehrlichman, another top Nixon White House aide, and John Mitchell, his former attorney general and campaign chairman, were indicted in 1974 and accused of making “offers of leniency, executive clemency, and other benefits” to obstruct justice. All three eventually went to prison.

Nixon was made an unindicted co-conspirator and resigned that August without ever using his pardon pen. But he received one himself a few months later from President Gerald Ford, who wanted to spare the country the spectacle of a former president put on trial.

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