Setting the stage for the Senate’s latest judicial battle, Judiciary Committee Democrats are gearing up for a nomination hearing Tuesday by preparing a line of questioning that could encompass a decade’s worth of Washington scandals.

Most importantly, Democrats plan to question Brett Kavanaugh, a former aide in the White House Counsel’s office, about whether he or anyone else in the Bush administration saw any of the more than 4,000 Democratic memos that were taken off committee computers in 2001 and 2002.

Kavanaugh, whose main responsibility in the counsel’s office was overseeing judicial nominations, previously worked in the Independent Counsel’s office under Kenneth Starr and authored key portions of the Starr report, which called for Bill Clinton’s impeachment in 1998. That period with Starr has led Democrats to express concerns about Kavanaugh’s views on privacy and prosecutorial conduct in his bid to land a lifetime seat on the U.S. Court of Appeals for the D.C. Circuit.

“There will be a ton of questions,” said Sen. Dick Durbin (D-Ill.), a Judiciary member. “He opens so many doors into areas of inquiry.”

Kavanaugh’s confirmation prospects appear very slim at the outset given the current blockade Democrats have imposed on all judicial nominees sent up by President Bush in the wake of the president’s decision to give recess appointments to a pair of controversial circuit court judges. That impasse has shown no signs of ending as Democrats continue to demand Bush promise in writing that no more judges will be given recess appointments, a request that Senate Republicans are adamantly opposed to.

But Kavanaugh’s hearing could spark the most political fireworks of any judicial nominee so far this year because the unique perches he’s occupied throughout his relatively brief legal career have put him at the center of some grueling partisan fights.

From Starr to Monica Lewinsky to Manuel Miranda — the former GOP staffer at the center of the improperly accessed Democratic memos — Kavanaugh has connections directly or indirectly to a host of scandal figures who have irked Democrats in recent years.

Republicans defend Kavanaugh, now a close Bush aide serving as White House staff secretary, as a sharp legal mind who has been awaiting a hearing since last summer.

“He’s certainly waited there long enough. Frankly, he’s a fine, fine man,” said Judiciary Chairman Orrin Hatch (R-Utah).

But Democrats question the amount of legal background Kavanaugh, 39, has to qualify him for a seat on the D.C. Circuit, often considered the second-most important court in the nation because of its wide-ranging jurisdiction. They are expected to argue that Kavanaugh’s experience is predominantly as a partisan lawyer who has been, as one Democratic aide put it, “a guy who was raised at the right-wing nipple.”

Sen. Charles Schumer (D-N.Y.), who has proven to be one of the toughest inquisitors of Bush nominees, is expected to be the lead questioner for Democrats at the Kavanaugh hearing, as he has done for other high-profile D.C. Circuit nominees including the 2002 hearing on Miguel Estrada.

Most recently Kavanaugh worked for two years in the White House Counsel’s office, helping select and prepare nominees. Throughout a three-and-a-half-month investigation by the Senate Sergeant-at-Arms Office, Democrats contended that some aides in the White House Counsel’s office must have seen or been briefed on the contents of their memos that were taken.

In late February, Judiciary Democrats sent White House Counsel Alberto Gonzales a letter pointedly asking whether he or any of his staffers had seen the memos and requested a listing of any contacts his staff had with Miranda or outside conservative groups that worked on the nomination issue.

Gonzales declined to answer which of his aides had contacts with Miranda and, in a brief letter in early March, said he was not aware of any credible allegation his staff had seen the memos and therefore had not investigated the matter. Democrats were infuriated by the letter and are anxious to pointedly ask Kavanaugh about his contacts with Miranda and other conservative activists.

Some Judiciary Republicans have supported the Democratic call for an independent-minded U.S. attorney to investigate whether any crimes were committed in taking the documents, and say questioning Kavanaugh about it won’t be a bad thing. “I don’t think it’s an unfair line of questioning,” said Sen. Lindsey Graham (R-S.C.).

Kavanaugh’s job required that he deal with individuals such as Miranda, who in 2001 and 2002 worked at Judiciary, and outside groups such as the Committee for Justice. In June 2003 Kavanaugh was one of dozens of key Bush administration and Senate Republican staffers to attend a fundraiser by the Committee for Justice at which George P. Bush, the president’s nephew, was the keynote speaker.

While in the counsel’s office Kavanaugh was also at the center of a few other decisions, including one to restrict access to presidential documents traditionally released after 12 years. Democratic staff said this was a bit of legal irony since, while working for Starr, Kavanaugh spent a lot of time and effort trying to unseal documents on which the Clinton administration claimed executive privilege.

His connections to Starr are an obvious source of anguish for Democrats. “Having been Ken Starr’s right-hand man, he comes in raising a lot of questions on our side,” Durbin said.

Graham, however, defended Kavanaugh’s experience with Starr. “The fact that he worked for Judge Starr is not a disqualifier for me,” said Graham, who was one of the impeachment managers as a Member of the House.

Kavanaugh first worked for Starr in the Solicitor General’s office at the end of the first Bush administration. When Starr became independent counsel in 1994, Kavanaugh joined him. He did a brief stint with Starr’s old law firm, Kirkland & Ellis, in 1997 and rejoined the Office of the Independent Counsel in 1998 when the Whitewater probe turned into the Lewinsky investigation regarding perjury and obstruction of justice.

After leaving Starr’s legal team in 1998, Kavanaugh rejoined Kirkland, and then joined the White House Counsel’s office in early 2001. Currently serving as staff secretary, Kavanaugh is in charge of all documents that Bush sees and is always close to the president.

In a December New York Times profile of life on the Bush family ranch in Crawford, Texas, Kavanaugh was described as one of three close aides to Bush who live in a “fraternity-house existence” in a double-wide trailer on the ranch.