Trump's inability to match Clinton is due to three factors. First, because he is an outsider, he has not attracted traditional Republican mega-donors. Second, Trump doesn't seem as motivated to raise money as Clinton is; typically, whenever Clinton flies somewhere to give a speech, she also finds time to hold a fundraiser -- Trump doesn't do this. And finally, Trump believes that he can run his campaign on the cheap because he is such a well-known media personality.
4. Believing he can run an unconventional campaign. Trump believes that he is "the smartest guy in the room" and, therefore, doesn't need to rely upon seasoned campaign professionals to run a conventional campaign. For example, Trump isn't running national TV ads because he believes that he generates the same amount of news with his daily campaign activities (plus his use of Twitter). Thus Clinton is outspending Trump on TV advertising. (NPR reported that, in 7 battleground states, Clinton is outspending Trump by $127 million to $18 million.)
Trump is also being outspent on field operations in swing states. For example, The New York Times reported that Trump's Ohio field operations were late opening and are underfunded: he has 15 offices in Ohio and 70 paid organizers; in contrast, Clinton has 35 field offices and 170 paid organizers. (And Ohio is the swing state where Trump has the most mature field operation.)
At the moment, Clinton leads Trump in all the swing states -- except for Iowa. Trump continues to disparage a conventional get-out-the-vote effort, but many experts believe this can generate a voter differential of several percentage points on election day.
Bottom line: Trump is going to lose because he is alienating critical voting blocks, underfunding his campaign, and ignoring the importance of get-out-the-vote field operations. Traps he set for himself because of his personality disorder.
(Note: You can view every article as one long page if you sign up as an Advocate Member, or higher).