Senator Mitch McConnell, the Republican leader, told President Trump this past week that Judges Raymond M. Kethledge and Thomas M. Hardiman presented the fewest obvious obstacles to being confirmed to replace Justice Anthony M. Kennedy on the Supreme Court, according to Republican officials briefed on the conversation.
While careful not to directly make the case for any would-be justice, Mr. McConnell made clear in multiple phone calls with Mr. Trump and the White House counsel, Donald F. McGahn II, that the lengthy paper trail of another top contender, Judge Brett M. Kavanaugh, would pose difficulties for his confirmation.
Mr. McConnell is concerned about the volume of the documents that Judge Kavanaugh has created in his 12 years on the United States Court of Appeals for the District of Columbia Circuit, as well as in his roles as White House staff secretary under President George W. Bush and assistant to Kenneth W. Starr, the independent counsel who investigated President Bill Clinton.
The number of pages is said to run into the millions, which Mr. McConnell fears could hand Senate Democrats an opportunity to delay the confirmation vote until after the new session of the court begins in October, with the midterm elections looming the next month. And while Judge Kavanaugh’s judicial opinions are publicly known, Mr. McConnell is uneasy about relitigating Bush-era controversies, the officials briefed on his discussions with Mr. Trump said.
With Senator John McCain’s absence because of brain cancer, Republicans have just 50 votes, and Mr. McConnell does not want to draw the ire of his libertarian-leaning Kentucky colleague, Senator Rand Paul, who opposed hawkish Bush policies. Aides to Mr. Trump and Mr. McConnell declined requests for comment.
Mr. McConnell is similarly wary of imperiling the votes of two moderate Republicans, Senators Lisa Murkowski of Alaska and Susan Collins of Maine. He has told Mr. Trump he could lose the two senators, who support abortion rights, if he picks another judge seen as a contender, Amy Coney Barrett, an outspoken social conservative who some observers believe may be more open to overturning Roe v. Wade.
On Saturday afternoon, Mr. Trump was undecided about his pick — which he has said he will reveal in a prime-time address on Monday night — according to three people in contact with him. He went back and forth every few hours between the four options in front of him, with Judge Kethledge getting the least attention, people familiar with his thinking said. It is similar to how Mr. Trump has approached most of his self-imposed deadlines for appointees, toggling between choices until nearly the last moment.
Mr. Trump, who in recent days has made mocking reference to the #MeToo movement at a rally and in private conversations, is said to be intrigued by the political statement of picking a woman. But he also likes Judge Hardiman, whom advisers say Mr. Trump came close to picking in 2017 before choosing Neil M. Gorsuch to fill his first Supreme Court vacancy.
The president’s only public statement about the choice confronting him came in a tweet from his golf club in Bedminster, N.J., where he was spending the weekend. “Big decision will soon be made on our next Justice of the Supreme Court!” he wrote.
Judge Kavanaugh, who has been seen as the front-runner, has inspired a broad campaign among supporters, but also a round of criticism from some Republicans, who have called his decisions in abortion and health care cases insufficiently conservative. His supporters have scoffed at the notion he is not conservative enough.
Mr. Trump’s hurdles with Judge Kavanaugh have been less about his judicial rulings than his proximity to the Bush family, of whom the president remains deeply skeptical, according to two people who have spoken with him.
Judge Kethledge is a Midwesterner who has issued strongly conservative rulings on immigration, religion, campaign finance and gun rights. Like Justice Gorsuch, Judge Kethledge served as a law clerk to Justice Kennedy. But unlike most recent Supreme Court contenders, he graduated from a public university’s law school, at the University of Michigan, and he has spent less time in Washington than many.
Judge Hardiman has built a reputation as a reliable conservative on the federal appeals court in Philadelphia, where he has served alongside one of Mr. Trump’s sisters, Judge Maryanne Trump Barry, who is said to have recommended Judge Hardiman for the Supreme Court vacancy last year.
Mr. McConnell has spoken to Mr. Trump or Mr. McGahn, or both, every day since Justice Kennedy announced on June 27 that he was retiring from the court. He has counseled them that there is no margin of error because the timing of the Senate’s court vote is so close to an election that could hand control of the chamber to Democrats.
Three red-state Senate Democrats up for re-election this year voted to confirm Justice Gorsuch, and Mr. McConnell is hopefulthey will support the next nominee. But his advisers say he is prepared to push through the nominee with only Republican votes — and that is why he is sounding notes of caution about Judge Kavanaugh and Judge Barrett.
Mr. McConnell was originally hopeful that Mr. Trump would select Amul Thapar, a federal appeals court judge who was previously on the bench in Kentucky, but has concluded that the president is unlikely to name him.
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