Among the potential candidates the White House is considering to replace Eric Holder Jr. as attorney general are Donald Verrilli Jr., the current U.S. solicitor general; Kamala Harris, California’s attorney general; and Sheldon Whitehouse, a two-term Democratic senator from Rhode Island.

White House officials have known about Holder’s plans to step down for months, but the decision wasn’t finalized until Holder and President Obama discussed it in a one-on-one conversation over Labor Day weekend. As recently as this August, Obama was still trying to persuade Holder to stay, according to a source familiar with the conversation. While vacationing around the same time on Martha’s Vineyard, Obama gently pressured Holder to rethink his plans to retire, even waxing nostalgic about the heady days of the 2008 campaign when the two men cemented their personal friendship.

Obama knows that getting a new attorney general confirmed by the Senate — which could possibly be controlled by the Republicans come January — will be challenging, particularly deep in the second term of his presidency.

White House officials have been quietly vetting potential candidates for months, according to knowledgeable sources. One source identified Verrilli as the leading candidate right now. Verrilli gained national attention when he defended the legal challenge to the Affordable Care Act before the U.S. Supreme Court in 2012. It was widely panned as a wobbly performance, but he prevailed in the end. Obama called to praise him both after the oral arguments and after the victory. Verrilli also served as a lawyer in the Obama White House, where he was well respected for his legal acumen and beloved for his gracious personality.

Solicitor General Donald B. Verrilli Jr. speaks during a forum at the Georgetown University Law Center, on Friday, March 9, 2012, in Washington, D.C. (AP Photo/Haraz N. Ghanbari)

Kamala Harris, the attorney general of California and a rising star in Democratic politics, is also considered a serious contender, should she be interested in the job. But Harris, a former district attorney in San Francisco, may have other political ambitions, such as running for the U.S. Senate or eventually for governor of California.

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Sen. Whitehouse has some clear advantages going into the race to succeed Holder. Whitehouse, who is close to Holder, served as U.S. attorney in Rhode Island in the mid-'90s and has been an important administration ally on the Senate judiciary and intelligence committees. The tradition of senatorial courtesy could smooth Whitehouse’s confirmation, should Obama decide to nominate him. But going for the attorney general’s job would mean giving up a safe Senate seat, which is something many Democrats would be loath to see him do.

Other potential candidates for the position include Deval Patrick, the sitting governor of Massachusetts, who headed the Justice Department’s Civil Rights Division under Bill Clinton, and Thomas Perez, the current secretary of labor and a former head of the Justice Department’s Civil Rights Division under Obama. Privately, Obama has expressed interest in nominating a Latino to head the Justice Department. Perez’s parents were both immigrants from the Dominican Republic. Another potential contender is Kathryn Ruemmler, Obama’s White House counsel until last spring and a former Justice Department official.

Sen. Sheldon Whitehouse, D-R.I., a member of the Senate Committee on Environment, at the Capitol in Washington, on Tuesday, March 11, 2014. (AP Photo/J. Scott Applewhite)

Holder, who evolved into one of the leading liberal voices of the administration, has been a persistent lightning rod for Republican anger. But during the first years of his tenure, he also suffered recriminations within the Obama administration for his handling of national security issues, including his decision to try the 9/11 defendants in Article 3 federal courts instead of military commissions. His push to try Khalid Sheikh Mohammed in a federal courtroom in Manhattan was severely criticized by members of Congress from both parties and ultimately was reversed under pressure from the White House. At one point in 2010, Holder’s spirits sunk so low that he seriously considered resigning. He was talked out of it by his good friend Valerie Jarrett, Obama’s closest adviser.

Toward the end of his first term in office, Holder began pivoting toward issues that were closer to his heart than national security, such as civil rights and reforming the criminal justice system. He has pushed hard to eliminate racial biases in criminal sentencing and to find alternatives to incarceration, the subject of a speech he gave earlier this week in New York.