"President Trump is being played," Lee, a professor at the Fletcher School of Law and Diplomacy at Tufts University, said on CNBC's "Power Lunch."
"Moved by hubris, among other things, [Trump is] presuming he can get the North Korean dictator to give up his nuclear arms, the one ace card that North Korea has in overturning the tables against South Korea."
North and South Korea have been divided for more than half a century. The North is technically still at war with the South and the United States.
Lee said the 34-year-old North Korean dictator is "putting on an elaborate show," one in which he hopes to gain power over the South.
"How do you do that?" Lee said. "Grow your economy? Use soft power? No. North Korea doesn't have those things. North Korea does have menacing nuclear power."
On his way to the Singapore summit, Trump was asked whether he will be able to tell if Kim is serious about negotiating. "I think within the first minute," Trump replied.
"Just my touch, my feel. That's what I do," Trump continued.
But Lee said it's simply not possible, "to assume that we can get this done by his charisma, by President Trump's art of the deal and so forth."
"Kim Jong Un has been preparing for this moment his entire life, receiving leadership training," Lee said.
"Underestimating the North Korean leader, thinking he's weird and crazy and being surprised to find out he's not only not a lunatic, but quite reasonable and charming, has been a fallacy," Lee said. "Repeatedly, Americans have been played by their assumption of North Korea as an underdog."
Part of the problem is that the two countries want different things, Alexandra Bell, senior policy director at the Center for Arms Control and Non-Proliferation, told CNBC.
"For the United States, we want to see the complete, verifiable, irreversible disarmament of the Korean peninsula — a very high bar," Bell said on "Power Lunch."
"For the North Koreans, what they want is regime security and more access to the international market," she said.
Lee said the summit, however, is a political move, one in which Kim can "buy time and money to do what he really wants to do, which is to further advance his nuclear and missile, menacing capabilities."