Bruce Heyman has encountered some complications during vetting, but so far there are no insurmountable obstacles in his path to the job, says a source familiar with the discussions.
In a story Wednesday about Canadian complaints over the delay in naming a new U.S. envoy to Canada, the Washington Post reported that Heyman has already undergone the State Department's diplomatic "charm school" training, an almost certain sign that he'll soon be announced publicly as Obama's pick.
Heyman hasn't returned calls this summer. Repeated requests for information from both the White House and the State Department about who's replacing David Jacobson, the former U.S. envoy who left the post in July, have also gone unanswered for weeks even as the administration announced a slate of other ambassadorial nominations.
Colin Robertson, a former senior Canadian diplomat who spent years at the Canadian embassy in Washington, says his White House contacts have suggested the reason for the delay in announcing Jacobson's replacement has nothing to do with American neglect of Canada and everything to do with politics.
Heyman's nomination will require Senate confirmation, and with the Keystone XL pipeline a hot potato issue in Congress over the past few months, the White House has likely decided to take its time rather than risk having to make any promises on the project in exchange for a green light for the Chicago financier's appointment.
"I've been told they're not going to put anyone up with all the Keystone stuff going on," said Robertson.
Instead, Robertson said, the nomination will probably come this fall and could fly under the radar of a Congress preoccupied with immigration reform, budget battles and a vote on whether to authorize the use of force against Syria.
Public records show that Heyman and his wife, Vicki, have been donating to Obama since 2007. They are what's known as "mega-bundlers" in American political parlance — in other words, top fundraisers.
Both Heymans served on Obama's National Finance Committee in 2012, helping to raise millions for his re-election campaign. The Chicago Tribune described Vicki Heyman as among the "local workhorses of the campaign ... regularly at Obama headquarters" in a report four months before the presidential election.
Heyman has been with Goldman Sachs since 1980. For the past 12 years, he's helmed the firm's Midwest private wealth-management group, covering 13 states and the western half of Canada.
The finance guru has also publicly sung the president's praises, not common among Goldman Sachs executives. While the company was a big Obama donor in 2008, executives were miffed by what they perceived as regulatory attacks from the White House and personal attacks on their character, donating instead to Mitt Romney and the Republican party in 2012.
"I am sensitive to the emotions" of Wall Street, Heyman told the Wall Street Journal last year. "But if you look at the facts, Mr. Obama is pro-business."
Some career diplomats have griped that choosing another Obama fundraiser for the job, when there is so much on the plate in terms of bilateral issues between the U.S. and Canada, suggests the president doesn't value the importance of the position.
"A lot of the criticism we're hearing about Heyman is the kind of stuff I heard before Jacobson came. He was not a career diplomat, his sole credential was raising money, he didn't have any ties to Canada," he said.
"But Jacobson was a very good ambassador. He was a point person, a problem-solver, he worked hard, he had a fantastic relationship with Gary Doer, the Canadian ambassador to the U.S., and most importantly, he had the president's ear. Having someone in Ottawa who can pick up the phone and get through to the White House is really important."
David Wilkins, ambassador to Canada under George W. Bush, said his close relationship with the president was one of his biggest assets as envoy.
"It's far more important that the U.S. ambassador has a relationship with the president of the United States than prior knowledge of Canada," he said in an interview.
"You can learn about Canada, and you're surrounded at the embassy by career foreign service workers who will bring you up to speed. But what is invaluable, and what many career diplomats don't have, is a relationship of trust with the president. I had it, and it was more important than a pre-existing relationship with Canada."