A vocal critic of Trump throughout the campaign, Chertoff began his interview Friday with Erin Burnett
by congratulating the man that will soon become the nation's 45th commander in chief.
"I have to take my hat off to him, because he demonstrated an ability to read the mood of the American public that confounded all the data crunchers, and I think you have to give him some credit for that," said Chertoff, before couching his praise with a word or two of caution.
"It's still early and obviously he hasn't even started in office yet. But at least I'm encouraged that what we're hearing seems to be sober, disciplined and appropriate."
As the topic turned to one of Trump's most recent and controversial selections -- retired Army Lt. Gen. Michael Flynn for the role of national security adviser
-- Chertoff was hesitant to condemn the appointee based solely on opinions expressed 140 character bursts.
Referencing Flynn's provocative tweets
, which strongly endorsed Trump throughout the campaign season, Chertoff pushed for big-picture analysis.
"Obviously any statement that someone makes you have to consider," he said. "But I'm very reluctant to regard tweets as a real measure of what a person thinks."
Also tapped by Trump on Friday was Jeff Sessions
, a veteran US senator from Alabama whom the President-elect picked to be attorney general.
The first sitting senator to endorse the business mogul during his surprising run to the White House, Sessions joins Trump in favoring a strict approach to immigration policy.
Though Sessions has faced accusations of bigotry
during his political tenure, Chertoff suggested that such decade-old claims may be overstated.
"I found Sen. Sessions to be knowledgeable, smart, willing to engage and willing to listen," Chertoff told Burnett. "People I know who actually were closer to him are really willing to vouch for him for being someone who's not carrying any kind of racial animus."
The appointments of Flynn and Sessions were two of three headline-grabbing decisions shared by Trump on Friday, as he also asked Rep. Mike Pompeo of Kansas to be CIA director, furthering the notion that the President-elect is surrounding himself with those that will support the hard-line agenda he promised throughout