The Press Herald’s query “If you could ask Donald Trump one question, what would it be?” in advance of his appearance in Portland on Thursday provided a range of questions – some better suited for Trump’s hair stylist than the candidate himself.

With the Republican candidate for president scheduled to hold a town hall-style meeting at 10 a.m. Thursday at Merrill Auditorium, the Press Herald decided to solicit questions from readers.

More than 100 people responded to the question posted on the Press Herald’s website and Facebook page. Trump, whose campaign has been marked by a series of controversies, this week finds himself embroiled in a scathing rebuke for comments he made to the Muslim parents of a fallen U.S. war hero. He also this week has been challenged on his understanding of the relationship between Russia and the Ukraine.

But by far the question asked most by Press Herald readers was why Trump, a billionaire New York businessman, hasn’t released his tax returns. Others asked him about his relative lack of experience to lead the country – “Would you hire you for this job?” asked Diana S. Others wanted to know if he’s afraid to debate Democratic challenger Hillary Clinton, and if elected, would he put her in jail.


A few respondents wanted serious answers to serious questions:


• How do you feel about or justify the fact that casinos – which you proudly point to as examples of your achievements and sacrifices for this country – have been shown to transfer wealth from lower and middle classes to the upper classes? – Tom of Portland

• If elected president, would you continue manufacturing your merchandise overseas, or would you move them to the USA and create more jobs here? – Trudy M.

• How would you stop Putin from taking over all of the Ukraine? Please be specific. Would this include US military intervention, and if so, in what form? – Lisa C.

• Can you build an east to west energy route, thus opening Maine to cheap electricity and natural gas? – Noah C.

• What would you do to improve the K-12 education system to better prepare our students for the real world – without putting the burden for more data collection on our educators? – Heidi S., who added she would ask the same question of Clinton.

• Trump Tower was built by S&A Concrete, whose owners were “Fat” Tony Salerno, head of the Genovese crime family, and Paul “Big Paul” Castellano, head of the Gambinos, another well-known crime family. If you did not know of their ownership, what does that tell voters about your management skills? – Tim M.



Others were looking for insight into his personality and values:

• What do you feel is the BIGGEST misperception that voters have about you, and WHY? – Dave S.

• 1. Name a politician that you respect. 2. What advice or lesson has that person given you that you use? – Shannon

• What do you say to all the contractors and trades people who suffered financially from your business practices and bankruptcies? – Donna

• Why do you think that it is okay for you to insult everybody who disagrees with you? – Bill S.


• Have you every apologized to anyone? Or admitted you were wrong? – A Mainer in Arundel


And then there were the flippant remarks:

• Could you demonstrate some common sense and please just shave your head? – Anonymous

• What’s the Pantone match for that skin color of yours? – J.E.S.

• Who dared you to run for President and where can I find them? – Dave


• You’re so big on helping middle class America … Can I borrow 50 grand? – Lisa of Hartland


Although the majority of respondents asked questions related to issues, a few were reserved for the media:

• Do you expect the local media such as the Portland Press Herald to cover this election with unbiased objective reporting or do you believe you will receive a consistent negative focus while your opponent receives positive coverage? – Christopher B.

• I can’t wait to see the same article posted when Hillary comes to Portland in search of big money from the Maine Wall St. crowd she loves so much. – N. R-S.



Trump, who’s trailing Clinton by seven points in post-Democratic convention polling, has his fans in Maine. Some of them chimed in:

• How does it feel to know you’re going to be the next president of the USA and fix all the problems we have that the Democrats have made during the past eight years? – Linda G.

• Why must you be so controversial even to your own detriment? Stop making us cringe, if you want our vote. Turn the page, you’re only giving crooked Hillary more fodder. – Phil M.

• Why did he choose such a right wing nut as his VP, when he could have selected another moderate business mind? – Stacey G.

• Mr. President Trump, when will you put the lying crook Hillary in prison? – Brian N.

Go to the Press Herald Facebook page or comment on this story to post a question yourself.

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