At the closed-door retreat hosted by the American Enterprise Institute in Sea Island, Ga., Cheney respectfully but repeatedly and firmly pressed Pence on a number of the president's foreign policy moves.
The Washington Post reports that the two clashed at a closed-door retreat hosted by the American Enterprise Institute in Georgia, on subjects including the withdrawal of troops from Syria and the tougher stance taken by the Trump administration toward North Atlantic Treaty Organisation.
The questions were a departure from the set of subjects that had been agreed upon for the meeting, which was attended by 200 select guests.
Trump Jr. slammed former Vice President Dick Cheney for comparing Trump to ex-President Barack Obama on foreign policy.
At one point, Pence, whom attendees described as taken aback by some of the questions, turned to his predecessor and inquisitor and joked, "Man, who wrote all these softball questions?"
Though Cheney has avoided the spotlight over the past few years, his remarks over the weekend were not the first criticisms of Trump.
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The former vice president reportedly brought up the fact that Trump "supposedly doesn't spend that much time with the intel people, or doesn't agree with them, frequently".
Cheney homed in on two key issues, attendees said: The president's tendency to make policy decisions on Twitter before notifying senior members of his own staff, let alone important allies, and his tendency to make such decisions without properly consulting aides and intelligence reports. Cheney also anxious aloud to Pence that "we're getting into a situation when our friends and allies around the world that we depend upon are going to lack confidence in us" and then offered a blunt criticism of the current administration's response to foreign policy challenges.
Cheney not only voiced frustration that Trump's foreign policy closely resembled that of Barack Obama, but also that it was a significant break from GOP presidents of the past. "But we think it's possible to demand that your allies do more to provide for the common defense of all of our nations and, at the same time, reaffirm our strong commitment-whether it be to the transatlantic alliance or to our allies across the Indo-Pacific".
The President's eldest son, Donald Trump Jr, jumped at the opportunity to lambast Mr Cheney's own record.
The civil but tense standoff put a spotlight on enduring fissures in the Republican Party over its foreign policy.
Mr Pence defended the administration and stuck by Mr Trump's push to win more financial help from allies and decrease the United States military footprint in Syria, while maintaining a strong posture overseas.