The post will be a mess. I started writing this post in 2014. And then it sat.

Over six years later, it became clear that I had chosen a huge topic. I decided I need to finish it any way I can in the fall of 2020. The topic I’m trying to cover here can be spread out in a couple of books if it hasn’t been already. But here’s my pitch if I was writing a book: The election of Barack Obama was historic. It showed how voters prefer a candidate with charisma and positive energy. It showed how Hillary Clinton, a good policy writer and party leader, wasn’t comfortable and charismatic enough to easily win the 2008 Democratic nomination. But in the aftermath of Obama’s election, old “third way” and corporation-friendly habits continued to steer Democratic leaders, and that, unintentionally, weakened them as a party and set the stage for a Donald Trump victory in 2016. We saw clear signs around the time Hillary Clinton chose Tim Kaine as her running mate in the summer of 2016.

The Democrats tried to play nice with a Republican party that was becoming much angrier, more radical, more anti-science, and simply more irrational. While trying to stay in power by being nice, they failed to build a lasting movement around Obama. Had they convinced a new generation -particularly young black men- to vote Democratic and stick to the party, they might have had a coalition strong enough to win in Michigan, Wisconsin and Pennsylvania in 2016, and thus block Donald Trump from becoming president. The way to build that coalition would have been to embrace a new generation of progressive policies like criminal justice reform, marijuana legalization, a federal $15 minimum wage, and the expansion of Medicare. But those ideas were seen as too left wing by Democratic leadership at the time. The Democrats declared good ideas coming from its younger and more academic members as too divisive and controversial before the voters had a chance to weigh-in on them.

I should end the post here! That’s my pitch! What follows are tangents and notes that would have gone into a book.

To start with one small example: the rise and fall of the conservative Democrats in New York state, known as the Independent Democratic Caucus (IDC) was a disaster. It is one of many examples how Democrats think they can stay in power by being moderate and allowing the GOP to dominate them, even when they are the majority. I’m not advocating that Democrats be a hard left party of no cooperation with the GOP, ever. If the GOP ever becomes a rational party, then some agreements can be made on repealing redundant or outdated regulations, reducing coin production, new treaties, and even some level of immigration and refugee policy reform.

But make no mistake, the GOP has been drifting more and more into madness since Watergate. With each new era, from Reagan, to Newt, to Obama, to Trump, the GOP has become more and more insane. So the window for bipartisanship might already be closed. And if that window is closed, then Democrats need to defend their platform and positions with more effort and focus. The voters have not rejected standing-up for progressive ideals. In fact they have welcomed it.

One of Obama’s biggest failures was not leaving the negotiating table when he was insulted and disrespected by Congressional Republicans. Obama made sure that he acted in a presidential manner. He also thought that he had to take the severe racist backlash, much like Jackie Robinson. It was impressive how Obama was aware of the racist insults hurled his way from every corner of our society, but he kept his discipline and didn’t acknowledge it. Even after he left office, he just didn’t talk about it. He slept well and enjoyed his massive wealth while the republic burned.

When will Democrats understand that we sometimes need to have national discussions about uncomfortable topics? Obama didn’t have to make it about himself. He could have sent Joe Biden to talk about racism. Send a surrogate. Delegate. Even when trump committed crimes against humanity in turning refugee children into orphans, Obama couldn’t manage to write a strong condemnation. He could only muster a passive criticism.

Now we have a president who only talks about himself, how he thinks he’s been treated, and vents his complaints and grievances about everything and everyone to anyone willing to listen to him. You could argue that Obama tried too hard to be presidential. You can’t really blame him. All his life, he had to be held to a higher standard because he’s black. But no one -not even him- could talk about that.

As president, what did Obama frequently do when he was at at the negotiating table? He offered the Republicans too much in his first move. Obama famously offered to sharply cut Social Security and Medicare in his 2013 budget before the Republicans brought it up. Thankfully, those cuts were not necessary, and even Republican senators opposed it. So why did he offer them? Obama was never challenged by the press nor his supporters on that odd and very damaging move. Obama must have really wanted to cut the programs, because he tried again the following year. He again put Social Security and Medicare on the table. And again, nearly all senators blocked that move, led by Bernie Sanders, in fact.

Americans wanted -and still want- an expansion of Medicare, even if they have to pay for it. But Obama took that off the table when the Democrats drafted the bloated 2010 Affordable Care Act.

The 2009 stimulus package, which did save this nation from going over a cliff, contained more tax cuts and temporary tax breaks than actual spending. It also didn’t include any criminal consequences for the Wall Street executives who blew up our economy with their complex and volatile sub-prime mortgage investment products. This was the greatest economic collapse in the United States in nearly 100 years. Not one banker was sent to prison.

But let’s end this post with the heart of the matter. Barack Obama’s two terms were not just a missed opportunity to build a solid Democratic majority. His two terms were a failure because he made terrible mistakes and wasn’t held to account by people who voted for him (unless you count the millions who defected in 2016 and voted for Trump, but that would mean that millions thought that Obama wasn’t terrible enough).

On one hand, Obama avoided confrontation too much. The man had too much class, but that hurt us. When Senate republicans blocked him from nominating a third Supreme Court justice, did Obama complain about it more than twice? A massive polarization was coming, and insiders saw it, but Obama chose not to start battles.

Before I dump what I have left of my notes for this point, I’ll some small examples of the many ways Obama failed. All of my next examples sat in one place - his cabinet. His Treasury Secretary was Tim Geitner. On paper, he had the qualifications. But as an apprentice and colleague of his predecessor, Hank Paulson, he was never going to be on the side of “Main Street.” Remember, Paulson and Geitner are the men who rescued Bear Sterns but chose to let Lehman Brothers die and take the whole US economy with it. Barack Obama campaigned on “change,” but the economic and banking management would mainly stay unchanged.

Obama’s cabinet also included Rahm Emmanuel as his Chief of Staff, an aggressive party elitist who used scorched earth tactics to protect Obama and elevate himself and his friends while doing the bidding of corporations. He managed to alienate every single faction of Chicago's Democratic coalition when he swooped in to take City Hall. He won no friends by becoming mayor of Chicago, and he left the local Democratic party shattered and I suspect, demoralized, as a new, disappointing mayor took over. Emmanuel also knowingly or unknowingly oversw a new era of torture conducted by the Chicago Police Department.

Leon Panetta is another terrible Cabinet choice. Beyond awful, whose memoir is an embarrassment for both himself and Obama. But I really want to shine a light on Obama’s Secretary of Education, Arne Duncan.

We might have the worst Secretary of Education now, but Duncan was easily the second worst. This is a supposed education expert who applauded the firing of the entire teaching faculty of a Rhode Island high school because the student grades on high stakes, standardized tests were low; the same man who dismissed childhood poverty as the primary reason for children's academic deficiencies in urban public schools, and whose entire tenure as Obama's education secretary was, in my opinion, a waste of a unique opportunity to actually improve public education. Basically, he’s the opposite of Jonathan Kozol, who addressed our education failings and their relationship to poverty head-on.

Obama’s cabinet sucked. It wasn’t a team of rivals. It killed any chance at progress.

And here, I reach the lightning round, since if I continued to write, Id’ write a book that’s probably already out there in the wild.

Obama’s failures also included:

• The expansion of NSA spying programs (such as the massive XKEYSCORE)

• The expansion of the drone and assassination squad war in countries that are not at war with the US (especially Yemen and Pakistan)

• The most aggressive war against whistleblowers in our nation's history

• The continuation of CIA and military torture programs (yes, we still outsource torture)

• A failure to hold the Bush-Caney administration to account for human rights violations and overseas torture programs

• The continued war against any and all reporting on that off-shore torture program

• A failure to hold the previous administration accountable for its violations of the constitution, while committing gross violations of its own

• This failure to investigate the Bush administration allowed Brett Kavinaugh to avoid what could have been a career-changing period, and might have prevented him from being nominated to the US Supreme Court 10 years later

• A failure to fully investigate the politicization of the Department of Justice under AG Alberto Gonzales (this is also the Democrats' failure in the House) 

• A failure to get the US out of Afghanistan within two full terms

• A failure to close the US military prison at Guantanamo Bay within two full terms

• A failure to curb defense (war) spending

• The failure to push for an expanded Medicare program for Americans, including a very fair, deficit-neutral idea to let Americans buy into Medicare and cover the costs themselves.

• A 2009 stimulus program that contained far more tax cuts than infrastructure spending 

• A failure to acknowledge that the most important thing our country can do to slightly curb the environmental catastrophe is to stop burning coal.

But we voters are not off the hook, either. This failure of one party, and the last four years under Trump is also our failure.

Because we’re stupid.

The great, American electorate is both ignorant and foolish. I know full well that politicians can never blame the voters. Conventional wisdom mandates a worshipful attitude toward the people who hold the future of our politicians in their hands. But let's be honest. Millions of Americans could not pass the simplest test oh the history or the government of this country. And they don't want to hear the truth about what needs to be done to solve the nation's problems. They want a full panoply of services, delivered perfectly, and AT NO COST TO THEMSELVES. Oh, and they want it now. Trump promised our voters precisely that absurd bag full of goodies, and far too many of our fellow citizens convinced themselves that the fat orange man with the funny golden comb over was going to deliver. Was Hillary a lousy candidate? You know she was. Is the Democratic Party led by a bunch of incompetent hacks? Is Santa Claus a jolly old elf in a red suit? Are Americans, by the millions, inexcusably ignorant, racist, selfish know nothings? Can you recognize rhetorical questions when you read them? The country's in deep trouble, and Americans are to blame.

Uncle Tim contributed to this post.