Samantha Vinograd is a CNN national security analyst. She served on President Obama's National Security Council from 2009-2013 and at the Treasury Department under President George W. Bush. Follow her @sam_vinograd . The views expressed in this commentary are her own. View more opinion articles on CNN.

(CNN) Both President Trump and North Korean leader Kim Jong Un expressed interest in a third summit this week, just two months after their meeting in Vietnam abruptly collapsed.

Trump has already struck out twice with North Korea, and barring any major strategic shifts, the third time probably won't be any different. Kim has successfully courted Trump by appealing to him directly, both through flattery and televised addresses. And since Trump kicked off diplomatic engagement with North Korea, Kim has only become stronger. It doesn't help that the United States has suspended military exercises in the region to placate Kim, which affects our readiness to respond to threats.

To make matters worse, Trump may be sending the wrong message by repeatedly undercutting his own team. Friday, Trump floated a possible plan to move migrants to sanctuary cities ostensibly to punish Democrats -- this announcement came just one day after his own team said the policy had been rejected . Because Trump keeps contradicting his own team on key policy issues, Kim may have reason to believe the President is riding solo on all things, including security decisions.

Given that Trump has politicized security decisions, Kim may be under the impression that the United States' security needs are an afterthought for a President who is hell-bent on campaign promises and scoring political points.

If the President logs out of his Twitter account long enough to listen to North Korea experts, they would likely advise him to temper his public displays of affection for Kim and share some analytic realities that he may not want to hear.

Strength in numbers

Typically, before presidents announce a willingness to meet with a foreign leader, experts present them with the current context so they can decide whether it's worth spending more time meeting.

The context for a third summit couldn't be clearer -- North Korea is stronger today than it was when Trump became president. Trump has already started campaigning against former Vice President Biden (who has not formally announced his candidacy) by raising the US policy toward North Korea under the Obama administration. But the truth is, North Korea has more friends -- and nuclear weapons -- today than under President Obama. The International Atomic Energy Agency and senior US officials have said that North Korea continues to build its WMD capabilities, including its nuclear weapons.

To top it off, North Korea has an increasing number of allies that are willing to accept or at least overlook its various illegal activities, including WMD proliferation, human rights abuses and cyber attacks. South Korean President Moon Jae-in has drawn much closer to the North Korean leader, and Moon is literally investing in the regime by keeping negotiations on track and pursuing joint economic projects with Kim

Kim is finding strength in numbers. While he's been developing a relationship with Trump, he's increased the number of nuclear weapons in North Korea, won friends around the world and pursued illegal transactions. President Trump has turned a blind eye to this activity and remains committed to staying in negotiations even though they're bearing fruit for Kim, and not for us.

Trapping Trump

North Korea continues to pursue a strategy that's worked well for Kim since last March -- he's appealing directly to President Trump, oftentimes through televised messages.

Isolating the President from his own home team is a winning strategy for Kim. Trump has shown that he puts more faith in what Kim tells him than analysis his own experts have been trying to get across: Kim has no intention of denuclearizing. And if the President's priority is really just propping up his own ego, he'll be reluctant to acknowledge that he's been played by Kim, which may give the North Korean leader more time to carry out his nefarious plans.

If the President actually gets briefed by his experts, they would probably warn him not to fall into Kim's transparent trap of personal flattery and criticisms of his administration. Otherwise, Kim will continue to toy with the President while he buys more time, develops more weapons and gains global acceptance as an illegally nuclearized power.

All options used to be on the table

Kim is also probably banking on the fact that even if President Trump abandoned negotiations, the US military is not as ready to respond to North Korean threats as it has been in the past. The US suspended joint military exercises with South Korea -- both because Trump said they were " very, very expensive " and to avoid upsetting Kim. Trump first canceled some of our exercises last summer after the first summit with Kim in Singapore, and he canceled more this year . Plus, Kim probably thinks that the likelihood of a US military strike is also degraded as South Korea gets more engaged on the ground with North Korea.

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Without a heavy dose of self-reflection and the willingness to put our country's security needs ahead of his desire to play a peacemaker worthy of a Nobel Prize, the President will probably try to schedule a third summit with Kim. But Kim will not change course unless we give him a real reason to do so, and any attempts to convince him that we're serious about denuclearization is going to take a lot of work. Meanwhile, Kim's counting on Trump being a creature of habit -- and those habits include putting his own ego ahead of the security needs of the American people.