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.