Bret kicked off Tuesday's show by welcoming Kellyanne Conway, Donald Trump's newly-appointed campaign manager. She began by analyzing the current state of the race. "Three weeks ago all the pundits were saying the race was over," Conway said, "but now the polls are tightening, especially in swing states. We are within the margin of error in Michigan and Pennsylvania and Ohio, and in those states we are leading among independents. He is such an unconventional candidate and I don't think polling captures the breadth and depth of his support. Donald Trump is closing the gap!" Conway looked ahead to Trump's Wednesday night speech on immigration. "You'll hear a consistent Donald Trump in that there will be no amnesty, no legalization, no sanctuary cities. We also want to be fair to the American workers, and there are a lot of folks who feel like they are competing with illegal immigrants. He wants to enforce the law and you will see one of the toughest speeches on illegal immigration in American history."

For another view, Bret asked Democratic strategist Richard Goodstein about Donald Trump's immigration policies. "Over the past week we have heard about Trump's 'softening' and 'hardening,'" Goodstein said, "but this is his signature issue and I think he's going to double down. He will say we want them all out, although he will equivocate as to how soon. This plays right into Hillary Clinton's message that Donald Trump is not equipped to be commander-in-chief, this is a gift to the Hillary Clinton campaign." Goodstein also vigorously defended the Clinton Foundation and praised the foundation's good works.

During a visit to Bangladesh, Secretary of State John Kerry advised the media to pay less attention to terrorist attacks. Bret spoke about that suggestion with Charles Krauthammer. "When you are living in an alternate reality," Dr. K said, "you want other people to join you. It is clear that John Kerry and the president have this view that the media and the public exaggerate the importance of terrorism. Obama sees terrorism essentially as a geopolitical nuisance and he wants to treat it that way, but the problem is that it kills a lot of people. The administration's idea is that if you ignore it the problem will go away, which is silly."

After Hillary Clinton's top aide Huma Abedin announced she was leaving her sexting-addicted husband Anthony Weiner, Donald Trump tried to make political hay of the tawdry situation. Bret spoke about that with Juan Williams and Lisa Boothe. "I don't think this is fair game," Williams protested, "because this is about the damage to a family and a child is involved. This is a family falling apart and you would think Donald Trump, who has been through two divorces, would appreciate the turbulence that family is undergoing. I don't think Anthony Weiner has access to any national security information." Boothe agreed that Trump crossed a line with his criticism. "Huma Abedin is certainly fair game in this election, but using her divorce is a little bit out of bounds. There's plenty of information for him to go after Huma without getting into the divorce."

For two more views of Donald Trump's upcoming immigration speech, Bret spoke with Juan Hernandez and Alfonso Aguilar. "Trump is going to say that he is presenting a more humane and just immigration plan," Hernandez predicted, "but he always slips back into hateful rhetoric. He has insulted me and my friends and my family members, there is no way he can win over Hispanics!" But Aguilar explained why he is supporting Trump. "I was offended by some of the comments Trump made during the primary, but I am far more concerned with the policies of Hillary Clinton in terms of the economy and Supreme Court nominations. We have to look beyond some of the words Donald Trump has used, he has always said he was open to having good people come back into the country. This is not about winning the Latino vote, this is about becoming more competitive in some battleground states."

Some polls show Donald Trump closing the gap between him and Hillary Clinton. Bret crunched the numbers with political observers Heidi Przybala and Philip Bump. "The stratospheric numbers that Hillary Clinton had after the Democratic Convention," Przybala stated, "are coming back to earth and this is a closer race. That being said, the fundamentals for Donald Trump are the same - he needs to win the states Mitt Romney won in 2012 and expand from that. At this point he is not doing that and it's even unclear whether he will be able to hold all the Romney states." Bump theorized that Donald Trump's primary mission is to make sure he wins the support of most Republicans. "He has to consolidate the Republican base because more Democrats support Hillary Clinton than Republicans support Donald Trump. It seems likely that he can pull some of those Republicans back in, but the real question is whether he can expand his support. Right now Hillary Clinton leads in all ten of the states that were the closest in 2012."

Returning for another segment, Heidi Przybala and Philip Bump looked ahead to the presidential debates. "Donald Trump is an agile performer and very spontaneous," Przybala began, "and he wants her to come off as being rehearsed while he's authentic. But in the primaries he was on a crowded stage with a lot of other alpha males, and in this case he will be on stage with one person who is preparing to hammer him on substance. Hillary Clinton will try to bait him on temperament and substance." Bump agreed that Secretary Clinton may try to challenge Donald Trump and hope that he loses his cool. "Donald Trump is fairly easy to goad and that is what the Clinton campaign is thinking about. But Trump won the primary by being himself and that seems to be the attitude he is taking in the debates. He has not recognized that the audience has changed and a risk will come if he does not change his debate style."