Which potential candidate would Trump have a harder time picking apart?

[Former Kentuckian]

Maybe Amy Klobuchar? But he'd still probably come up with some nickname for her. He already has a lot of material for Elizabeth Warren. With Gillibrand he'd probably come up with something based on her background with the Clintons and how she's "flip-flopped" from Blue Dog to Progressive. He'd probably go after Cory Booker for defending Bob Menendez and call him a "bad guy" or something. He'd needle Kamala over her San Francisco background. And we've already seen what he has to say over Biden and Sanders.

Edit: On second thought, he'd probably try to connect Klobuchar with Franken, although that could bring up the allegations against him again.

[Former Kentuckian]

JOE SESTAK.

Military. Moderate. And anti-establishment.

Did I inspire this a few days ago?

I think you're absolutely right for the record, but I think other options are also possible - John Allen had a great convention speech and has progressive credibility as president of the Brookings Institution, Bill McRaven has an incredible record (who can attack a Navy SEAL who took down Bin Laden?) and has made public statements against Trump's attacks on the media immediately after his inauguration. Seth Moulton also applies - very anti-establishment internal to the Democratic party with a stellar war record.

I've actually had my eye on Sestak for 2020 for some time now. It's just, all the pieces seem to fit so well with him. He's got military background, but not just any miltary background, he's an admiral! The highest ranking military officer ever to serve in Congress! Against an administration that's always pushing itself as pro-military and pro-"The Generals", "The Admiral" would literally be their worse nightmare. He may not be apolitical like RFKFan wanted, but his political credentials actually boost him IMO. He has strong liberal social positions (he helped lead the fight against DADT), but some more moderate fiscal positions. He also has very strongly liberal positions on healthcare, and an extremely sympathetic reason for his support for government health programs: His daughter survived cancer because of Tricare, the government's health program for military families. And to top it all off, the Democratic establishment hates his guts. They hate him for running against (and beating) Arlen Specter, whom they enticed to join their party to have an easier run for reelection. They hate him for not submitting his campaign in 2016 to the party machine. So none of Trump's "crooked" talk works on him at all!

Pair it with Harris and you have Trump's kryptonite.

I agree with some of your other picks there, however, I'm not sure if any of them have quite the combo Sestak has, especially with his extremely high rank.

Sestak might be a Senator now if not for all the idiotic national Democrats who shilled for McGinty.

God, she was such a garbage candidate. Why they all lined up for a Senate candidate who came dead last in the previous gubernatorial primary and couldn't even figure out how doors worked, I'll never know.

[Former Kentuckian]

What is this fetish for ex military men?

American nationalism

[Former Kentuckian]

Someone with a squeaky clean background.

LADIES AND GENTLEMEN, THE FORTY-SIXTH PRESIDENT OF THE UNITED STATES, MARTIN HEINRICH!

He ain't squeaky clean...

He's just squeaky