Sometimes he offers candid advice about his visitors strengths and weaknesses. With several lesser-known candidates, according to people who have talked to him or been briefed on his meetings, he was blunt about the challenges of breaking out of a large field. His advice is not always heeded. He told Patrick earlier this year that it was likely too late for him to secure money and talent if he jumped in the race. Occasionally, he can be cutting. With one candidate, he pointed out that during his own 2008 campaign, he had an intimate bond with the electorate, especially in Iowa, that he no longer has. Then he added, And you know who really doesnt have it? Joe Biden.
Publicly, he has been clear that he wont intervene in the primary for or against a candidate, unless he believed there was some egregious attack. I can't even imagine with this field how bad it would have to be for him to say something, said a close adviser. Instead, he sees his role as providing guardrails to keep the process from getting too ugly and to unite the party when the nominee is clear. There is one potential exception: Back when Sanders seemed like more of a threat than he does now, Obama said privately that if Bernie were running away with the nomination, Obama would speak up to stop him. (Asked about that, a spokesperson for Obama pointed out that Obama recently said he would support and campaign for whoever the Democratic nominee is.) ... Throughout 2017 the main struggle of the small staff Obama assembled in the West End was how to deal with what they viewed as a crazy president personally obsessed with Obama. After running against Obamas legacy, and then holding one awkward but collegial meeting in the White HouseHe knows absolutely nothing, Obama privately told a visitor about Trump, immediately after the meetingTrump discarded historical precedent and began attacking Obama personally as he worked to overturn his policies. For the most part, Obama and his staff chose to ignore the personal and weighed in only on big policy questions.
Even after the election, Obama still held out hope that he and Trump could have some kind of normal president/former president relationship, similar to how Obama and George W. Bush operated in 2009. He wanted to be a resource, said Kevin Lewis, Obamas first post-presidential press secretary. What we didnt expect at the level that it was done were the attacks. ... And then Joe Biden announced he would run for president. Presidents have always struggled with how much to support their vice presidents. At one level, a Biden win would be a profound vindication, an almost direct restoration of the Obama administration. But Obama had already passed over Biden for Hillary Clinton in 2016. With Biden out of the race in 2020, the psychodrama of their relationship and the intrigue about Obamas assessment of Biden could have been avoided. Obamas commitment to non-interference would have seemed less fraught.
Biden, Obama told people close to him before Biden even entered the race, would have to earn it. There would be no endorsement. (Biden has said he never asked for one.) Besides, he liked to say, fighting it out in a tough primary is what made Obama a strong candidate for the general election. ... Over the past year, Obama and his closest advisers were clinical in their assessments of the candidates. They discussed doubts about Kamala Harris appeal to African Americans. Obama was deeply skeptical about the prospects of Mayor Pete Buttigieg. During their West End meeting, he was complimentary about Steve Bullocks record as a governor and frank about his challenges: Nobody knows who you are, he told him.