WASHINGTON _ During the last contested presidential election, John Roberts flew to Florida as a private attorney to advise its governor, Jeb Bush, how to navigate the fight ahead.
The governor's brother, George W. Bush, won that contest at the Supreme Court against Al Gore in 2000, became president, and later appointed Roberts to the high court as chief justice.
Twenty years later, as the nation's top justice, Roberts hopes to avoid another Bush v. Gore scenario amid increasing signs that the 2020 election will be contested, with record mail-in voting across the country due to the coronavirus pandemic, legal analysts say.
In Roberts' public statements and his unpredictable court decisions, court watchers see a chief justice on a mission to preserve public confidence in the independence and integrity of the high court.
It is precisely the actions that Roberts has taken as a swing vote and a moderating force on the court that have conservatives, and President Donald Trump, rushing to fill a vacancy on the bench left by the death of Justice Ruth Bader Ginsburg before the Nov. 3 election and any challenges to the results that might follow.
"The pressure on Chief Justice Roberts will be enormous, especially if the seat is not filled and the election is challenged in the Supreme Court. He will want to avoid a 4-4 split or a 5-3 along party lines," said Alan Dershowitz, a constitutional law professor at Harvard and a lawyer to Trump during his Senate impeachment trial.
"His goal is to avoid the politicization of the Court and the perception that there are Republican and Democratic justices," said Dershowitz, who wrote a book, "Supreme Injustice," on the Bush v. Gore decision. "This vacancy at this time is his nightmare scenario."
There would be key differences from the 2000 case. This time, challenges could arise from multiple states with conflicting lower court decisions, and that litigation is already being prepared well in advance.
"We are going to have enormous litigation challenges that would make Bush v. Gore look like patty cake," said David Rivkin, a constitutional litigator who served in the White House counsel's office under former Presidents Ronald Reagan and George H. W. Bush.
And Trump appears to be preparing for it.
In recent days, the president has repeatedly told reporters that he wants to replace Ginsburg ahead of the vote so that nine justices are seated � including a new, reliable conservative � before the court hears any cases related to mail-in voting.
He plans to name his choice to replace Ginsburg on Saturday, and Republicans have signaled they have enough support in the Senate to proceed with confirmation hearings and a vote before Election Day.
"You're going to need nine justices up there. I think it's going to be very important," Trump said on Tuesday. "Because what they're doing is a hoax, with the ballots. They're sending out tens of millions of ballots, unsolicited � not where they're being asked, but unsolicited. And that's a hoax, and you're going to need to have nine justices. So doing it before the election would be a very good thing."
Filling the vacancy left by Ginsburg with a conservative judge would increase the chance of a decision along ideological lines that strips Roberts of his ability to serve as an arbiter or a swing vote, even if he were to vote with the liberal wing of the court.
"Having a Bush v. Gore-type scenario is probably Roberts' worst nightmare," said Ashley Baker, director of public policy at the Committee for Justice, who worked on the Republican effort to confirm Justices Neil Gorsuch and Brett Kavanaugh.
"Since elections inherently have winners and losers, Roberts can't 'split the baby' like he did in other controversial decisions such as the census case last year. If possible, he will avoid having to decide the election," she said.
Experts believe that Roberts will attempt to build consensus around any court ruling related to the election to avoid the 5-4 ruling that effectively halted a recount in the battleground state and contributed to the controversy around Bush v. Gore.
Thomas Jipping, a senior legal fellow at the Heritage Foundation, said it is "impossible to say" what the court would do before any election litigation has been filed.
"There's no way to know what a case related to the election would be, what issue would it raise, how would it get to the Supreme Court, what would the timing be," Jipping said.
But Rivkin said that challenges to mail-in voting will "inevitably" arise at the circuit court level, and those courts could have "inconsistent answers on the same legal issues."
He warned that the resulting confusion could keep the Electoral College from rendering a verdict when it meets on Dec. 14, making it the responsibility of the House of Representatives to pick the next president.
"That's the last thing we need as the back end of the national nightmare we've been living with pandemic," he said. "Whatever one thinks about who should win, my point is not this way. Not this way."
If Trump is successful, the newest justice would be his third appointment to the Supreme Court and the sixth member to be appointed by a Republican. The other three were appointed by Democrats.
The appointment would resolve what staunch conservatives, including Texas Sen. Ted Cruz, are arguing could lead to a constitutional crisis if Roberts voted with the liberal justices on election cases. A tie at the Supreme Court could create chaos around the election, they argue, if lower courts issue conflicting rulings and Americans lose confidence in the electoral process.
Those warnings have been dismissed as exaggerated by Democrats, who pointed out this week that the court also had a vacancy during the last presidential election year.
Conservative strategist and pollster Frank Luntz said that a 4-4 split vote ruling that conservatives are concerned about is the best argument Republicans have for filling the seat expeditiously.
"What he decides to do as the swing vote will decide the future of the world," Luntz said of Roberts if the vacancy is not filled and there are eight justices.
Trump has long been distrustful of Roberts, and the president on Wednesday echoed conservatives' concerns that the chief justice could side with liberals on mail-in voting cases that could come before the courts.
"This scam will be before the United States Supreme Court. And I think having a 4-4 situation is not a good situation," Trump told reporters. "I don't know that you'd get that. I think it should be 8-nothing or 9-nothing. But just in case it would be more political than it should be, I think it's very important to have a ninth justice."
Roberts' past rulings on the Affordable Care Act, the U.S. Census, and other high-profile cases have led to disappointment and skepticism from some conservative legal experts that he is not a reliable vote for their causes.
Conservative groups still feel "betrayed" by the chief justice over his decision on health care, said Adam Brandon, president of FreedomWorks, a conservative activist group.
"The mental jujitsu that he had to go through to make that ruling, it didn't seem like that was based on a legal principle as much as he was trying to find any justification possible for justifying the law," he said. "That makes me nervous."
The rulings have also contributed to concern in conservative circles that Roberts is factoring outside political pressure into his decisions.
"At the end of the day, for the court to be perceived as a political rather than a legal actor, undermines its legitimacy, and the fact of the matter is that those types of decisions from Chief Justice Roberts have only increased the perception of the politicization of the court," said Carrie Severino, president of the Judicial Crisis Network.
Leaving a vacancy on the court that would allow Roberts to act as a swing vote is not a risk that conservatives said they were willing to take.
"The pressures on the chief justice are sort of a symptom of exactly the problem that we would hope this nominee would be part of the solution to, which is that we put far, far too much emphasis on the Supreme Court, and for that matter on the federal government," said Casey Mattox, vice president of legal and judicial strategy at Americans for Prosperity.
"Our hope would be that this nominee restores the correct balance," he said.
