But Obama has not shied away from engaging with the former vice president.
"Cheney has been at the head of a movement whose notion is somehow that we can't reconcile our core values, our Constitution, our belief that we don't torture, with our national security interests," the president said in March.
On issue by issue, the two have squared off and spared no punches.
The president said the detainee center at Guantanamo Bay inflames anti-U.S. sentiment and is inconsistent with American values.
"We will close the Guantanamo Bay detention camp and determine how to deal with those who have been held there," Obama said right after taking office in January.
Cheney said last week: "Guantanamo Bay is a great facility. It's very well run. These people are very well treated."
Addressing the enhanced interrogation tactics of the Bush administration, Obama last month, "What I've said -- and I will repeat -- is that waterboarding violated our ideals and our values. I do believe that it is torture."
"It was done legally. It was done in accordance with our constitutional practices and principles," he said.
But perhaps their core disagreement is the fundamental approach to national security.
"We are going to be able to effectively balance our national security needs with our civil liberties concerns," Obama said in March.
Cheney countered: "This is a war. It's not a law enforcement problem."
White House officials say they are happy to have someone as unpopular as former Cheney emerge as their primary opponent in this national security debate. But Republicans say the fact that Obama is delivering a comprehensive national security speech today is evidence that Cheney's criticisms are gaining traction.
Obama is facing skepticism from more than just the former vice president.
Yesterday the United States Senate delivered a harsh rebuke to Obama with a 90-6 vote against the $80 million he requested to shut down that Guantanamo Bay prison.
The Senate's message was clear: do not close the Guantanamo detainee center until you have a plan of what to do with the detainees.
Nearly 540 detainees at Guantanamo Bay were transferred or released to foreign countries under President Bush. Now, 240 detainees remain, including those no other country has been willing to accept, ones the U.S. will eventually prosecute, and prisoners judged too dangerous to release, but the evidence against them would likely not withstand a trial.
The decision on what to do with the remaining prisoners is an especially complicated dilemma for Obama. Democrats and Republicans are promising a fight to keep the detainees not only out of the U.S. but even out of U.S. prisons.
When asked if he'd be comfortable with the prisoners being transferred to American prisons, Reid paused and said, "not in the United States."
Today Obama said that his administration will seek to transfer some detainees to "supermax" facilities in the United States, noting that nobody has ever escaped from one.
Obama is also considering sending roughly 100 detainees from Yemen to a rehabilitation center in Saudi Arabia. At least 11 Guantanamo detainees sent there by the Bush administration, however, have graduated and have become involved again with terrorism, including al Qaeda's deputy leader in Yemen.