During every Presidential cycle, why do we seem to elect the lesser of the evil?

'Democracy is the worst form of government, except for all the others.'

--Winston S. Churchill

The truth of the matter is a Two Party system or ANY party system has undermined the process. We no longer have the option to pick the Middle ground due to divisive politics from the wings. If you are Pro gun and Pro Gay marriage you are vilified by bother parties. Any candidate that is truly willing to work with both sides is never allowed to stand. They would undermine the power bubble the DNC and RNC hold.

Americans are so busy trying to survive they no longer look up and around at what Washington is doing. Look at all the social justice projects that keep popping up. Every time one is settled another one takes its place to distract. Do you think that is by coincidence? I am 41 and in my life race relations are at there worst, terrorists are running rampant, the economy has tanked, healthcare is a mess, Whole industries are under attack by Washington and people are worried about offending a man in drag trying to use the women's room? is that really an important issue to America?

The DNC and the RNC put forth their (best) and the "People" decided... or do they.
The Paid Media runs their agenda and TELLS America what there opinion should be. To many lemmings take the spoon feeding and that is why we now have a system of "The Lesser of Two Evils.

Because it's all about the money. The powers behind those running and the money they throw into it. There were many good choices this time, but those weren't bought and paid for. Why do you think Trump got where he is, he ran his primary campaign on his own money and every mainstream politician is pissed off at him. Well it's their own fault. If they'd been in there doing their job instead of screwing around. Need I say more.

Because there has not been any quality candidates since like the 80's. So we are stuck choosing between Bevis and Butthead every election.

The simple answer is voter apathy. My state had less than a 3rd of voters actually vote in the primary. 1/3 of the voters went out and chose who would lead our Country among other items on the ballot. Most times people believe their vote doesn't matter or because "well this election doesn't count anyways, so I'll wait until November. So let's use the Republicans as an example. They had 16 candidates at the start of the cycle and now they're down to 1. Imagine the difference if more people turned out to vote. Maybe Trump wouldn't have dominated in the polls. Maybe one of the candidates who dropped out early would have done a little bit better. By the time November comes along, we're left with the choices of what the minority picked out because the majority is definitely not deciding these elections.

It hasn't always been that way. Only since we began selling our votes

It's a combination of everything that people mention below. The system chooses to focus on negative attacks vs the plans and programs of a candidate. When was the last time you saw a political commercial where a candidate actually talked about what they would DO on some specific issue? No matter how much a candidate claims that they will not go negative in their campaign, they inevitably do. When all you have to choose from is what you can glean from negative advertising your natural reaction is to, as you say, choose the lesser of two evils.

Because political divisiveness has reached a crescendo. Both parties have ramped up to almost radical agendas.....just my opinion.

I'm a little distressed, but not surprised that you think the American public elects the "lesser of two evils." As a 2d Lt, you're possible young and infected by the liberal bias in our school and university systems. I have lived under every President since Eisenhower and voted in every election since 1968 (voting age used to be 21). I've seen a lot of Presidents whom I wouldn't consider "evil," that is, they intended to destroy the USA and demean the principles on which it was founded. You can make up your own definition of evil, but that's mine.

Kennedy was liberal for his time. Johnson was a practical advocate for civil rights, but prolonged the war in Viet Nam. Nixon got us out of Vietnam and opened relations with China; he was not as evil as you might think until he was caught up in Watergate. George HW Bush, and George W Bush were more conservative but never tried to destroy the US. Bill Clinton, serving between the Bushes, was more liberal, but was reined in by Congress and his propensity for sexual scandal. Unfortunately, I think Mr Obama was trying to destroy the US as originally founded. I think he was ultra liberal and tried to force those policies on the nation. His behavior gave rise to the Trump victory because most of the people in the nation didn't agree with his agenda--Mrs. Clinton was viewed as a continuation of Obama and rejected. Mr. Trump definitely isn't trying to destroy the nation as founded. He may destroy much of Mr. Obama's work, but that may be a good thing. He is trying to return the US to its rightful place in international relations and to bring us to a more traditional representative democracy in a republic with a smaller and less intrusive Federal Government.

If there was an "evil" in the last election, it was Mrs. Clinton based on her probable criminal actions as Sec State. Exit Polls showed more people voted "against" a candidate than "for" a candidate in 2016. Both candidates had asked voters to give them their vote because they weren't their opponent. It didn't work well for Mrs. Clinton.

Well, I've been trying to answer this question for an hour now, but a couple lines in, my political bias starts to creep in despite the fact this is NOT a partisan issue. Well, it wasn't all bias but every wording I had could have easily appeared to hold the threads of partisanship which is not the message I wanted to convey. So in lieu of a detailed post, I'll just say one thing followed by a couple quotes and answer questions and concerns as they come in.
I think our society has become to over-sensitive, lazy, and ill-informed to not only recognize leadership, but to actually shun leadership and instead embrace a manager, an organizer, or just someone who will tell them what to do and give them what they want instead of working toward something themselves.

"When trouble arises and things look bad, there is always one individual who perceives a solution and is willing to take command. Very often, that person is crazy." ~Dave Barry, "Things That It Took Me 50 Years to Learn"

"I cannot give you the formula for success, but I can give you the formula for failure, which is: Try to please everybody." --Herbert Swope

EDITED
Forgot one major factor. The media is highly partisan these days. There is not single unbiased news source in this country. One thing I picked up on that the media often decides who the choices are going to be. Think about this; how much media attention did Trump and Hillary get impaired to all the rest? Who are now the presumptive nominees? That's how we ended up with McCain years ago. That's how we ended up with Romney. That's how we ended up with Kerry and Gore. Perhaps the only election the media lost was Hillary vs Obama... but even though their choice of Hillary didn't win, they still won with Obama in the end. And this is why I do not read, view, or listen to MSNBC, CNN, FOX, PBS, NPR, CBS, ABC, NBC, Newsweek, Time, any major newspaper, or even the BBC.