I didn’t vote for Barack Obama in 2008, or in 2012. As regular readers will know, I also didn’t vote for the Republicans in those elections. I wanted to vote for him in 2008, came very close, but ultimately decided I couldn’t. I had been rooting for him throughout the primaries, I loved hearing him speak, but my calculus broke down as follows:

So while I’m excited about the upside possibilities, I have to decide based on what I can be confident Obama will actually do. He will surround himself with people like Joe Biden. Disaster. He will move troops from Iraq to Afghanistan and accelerate hostilities there. Disaster. He will attempt to enact tax policy that is exactly right for this time. Good. He will support measures like the $700 billion bailout that passed Congress earlier this month. Disaster. He will increase the amount of healthcare coverage in this country, though he may use mandates to do so. Toss-up. He will talk about hope and change and sacrifice and be aware of the times we are engaging in, as much as most any politician could. Good. He will talk to foreign leaders. Good. He will not commit to ending the war in Iraq. Disaster.

That’s a lot of disaster. I could be accused of being close to a one-issue voter in many ways… war and violence are pretty much the only thing I care about at the end of the day. I think tax policy is somewhat important, and certain social issues here and there (gay marriage, for example). And there’s an increasing issue about who will have the dignity to allow America to step down from its throne of arrogance and superpowerism to gracefully withdraw without pressing red buttons and going nuts. On that last front, Obama clearly beats McCain, though there’s little confidence I have that any American politician can really do that.

Ultimately, I can’t end up supporting someone who has made one of their only concrete policy articulations a description of exactly how many Afghans they want to kill. You can say all you want about him having to say that to get elected and that he’ll actually end both wars, but I need to see that happen before I have any reason to believe it.

In the end, I feel good about my decision not to vote for Obama, not to support accelerating the war in Afghanistan and, as became more important over time, the unending war with everyone via drone strikes. But as I’ve discussed frequently here, the last two years of Obama’s term were his best, by far, and agreeing to release Chelsea Manning capped a run of commutations, negotiations, and executive orders that made me truly sad we couldn’t have had six years of that President beforehand. Had Obama’s first four years looked like his last two, I probably would have voted for him in 2012. The fact that he released Manning after years of punishing whistleblowers and tightening the screws on American secrecy indicates that maybe his heart really was in the right place all along. Or that Trump had shown him the danger of building up the executive’s power to persecute individuals without remorse.

But how I feel about Obama has always been hard and hard to talk about. On Inauguration Day 2009, I stood in Freedom Hall at Glide in San Francisco, shoulder to shoulder with co-workers, homeless San Franciscans, addicts, and leaders. I was swept up in the moment, in the vast unconditional love and admiration, in the tears of all the African-Americans present, in the shaking weeping of Cecil Williams as he watched a Black man become President. I could feel the pulsating hope, the unbridled joy, the feeling of unexpected fulfillment, and my heart, too, was full. I wanted so badly to be wrong about Obama, for him to be the Socialist visionary that Cecil was, that the Republicans accused him of being. He wasn’t, of course. But that didn’t make his Inaugural Address or the speech in Chicago on Election Night that much less magical. The man has always been magical. He captivated our hearts and minds and, for all this flaws, never let them go.

This is the problem of Obama for a radical leftist. The man is so damn likable. He’s a grand orator and an eminently reasonable person. His family is so charming. Michelle Obama is his equal and perhaps a braver potential leader. Her speech at the DNC stole the whole show. I want to like Obama and his cadre and his aura so much, reinforced by all these positive memes and posts and adorations from 95% of my friends. And yet, as it takes someone like Larry Wilmore to remind us, the man is an unrepentant murderer. He has used American power to accelerate and reinforce the post-9/11 strategy and doctrine that we should kill everyone who disagrees with us, that we should maintain and expand imperial power through the use of force. It’s hard for me to square, to reconcile, with all his other rhetoric and his lofty speeches about hope, about being the people we’ve been waiting for. But it’s the reality and one that I have to work hard not to forget.

The other issue, of course, is that Obama’s philosophy was to negotiate himself out of the room. It’s hard to say how much of this was naivete or blind faith that the Republicans would be as reasonable as he was trying to be and meet him halfway or even the surreptitious belief that Republicans had better solutions than Democrats. Regardless, it’s impossible to ignore the fact that most of his legacy is cribbed from the Heritage Foundation (the ACA) and the W Bush Administration (nearly all the foreign policy besides the Iran deal and Cuba). He didn’t write a healthcare bill he wanted to see as a strong step toward socialized medicine with a robust public option. He asked Congress to write it, then made even more concessions. He didn’t push for a strong reconciliation in the Middle East, at least after his Egypt speech, and allowed Hillary Clinton to convince the rest of the Cabinet to bomb wherever possible. He understood that a lot of the strength of power is found in not using it all the time, but in so doing handed it to people far less hopeful than he. The result was that most of his policies, especially in the areas I care most about, looked like eight more years of George W. Bush.

On the other hand, of course, now we have Donald Trump as President. Trump is everything that Obama is not, as a human being. He is crass and classless, entitled and boastful, sexist and scornful. Where Obama preached hope, Trump preaches doom. They both advocated change, but much of Trump’s change is a reversal of Obama’s legacy. Of course, when Obama’s legacy looks a lot like W Bush, what do you do with that? Trump says he can replace the ACA with something cheaper that covers more people. And Obama has said that if someone can actually do that, he’ll support it. There’s a window here, a narrow one, for some actual real change and improvement. But it requires working with and trusting someone who has taken every step possible to make himself appear as an enemy of the people who supported Obama, the people who I care about most, the people who I generally agree with in direction, though I disagree substantially with in degree.

It also requires Trump not being an instrument of the party that reluctantly, nay, almost at gunpoint, got him to the White House. Trump’s rhetoric has always been far more populist than Republican, a third road entirely from the traditional parties. But his appointments, from Vice President throughout most of the cabinet, looks like he’s trying to usher in a mainline Republican establishment administration. Far from draining the swamp, he seems to be pumping water in from other wetlands, doubling down on rich old white men who care only about themselves and their bottom line. This, obviously, is the opposite of populism.

Yet the fate of the Trump years, however long they last, relies on the extent of division between Trump and the Republican Party. Many of his speeches, as even a PBS commentator observed during the Inauguration, sound like FDR. He talks about getting America back to work with an investment in infrastructure, building roads and bridges and even railways! Unlike FDR, of course, he touts an isolationist foreign policy. And while I would love to see an America that invests in the rest of the world without fighting with it, I strongly prefer isolationism to the policies of the last sixteen years. America’s role on the planet since 9/11 has been to bomb and to bully, to use 3,000 dead as an excuse to claim a moral authority we abdicate daily. Withdrawing from that entirely, resetting the position of our empire relative to the rest of the world’s people, is better than continuing to accelerate it.

Of course, to build investment in infrastructure while withdrawing from the rest of the world, Trump will have to resist Republican machinations. There’s a reason that the Republican establishment coronated Jeb Bush before the voters revolted. The Republican Party, in 2017, is still the party of Bush. The last two Republican Presidents prior to Trump have their hold on the collective imagination of the the party leadership. And Jeb wants privatization. Jeb wants America to bully more and bomb more. Jeb and friends will pull out all the stops to make Trump’s rhetoric as meaningless as Obama’s promise to close the prison at Guantanamo Bay.

On the flip side, both mainline Democrats and mainline Republicans agree that many of Trump’s policies – the worst he’s advocated – are garbage. Building a wall on the Mexican border, Muslim bans and registries, cracking down on immigration. No one besides Trump and his most rabid voters think these are good ideas. Again, American progress from 2017-? will depend on Republicans ditching Trump when they actually disagree. There’s a narrow window here, a window of possible hope in the darkness, where Republicans ditch Trump on his worst policies, stand against their “own” President, but acquiesce on matters like building new trains and roads and bridges. Or that enough of them acquiesce there and that Democrats see the opportunity to implement FDR-like policies even during a Trump administration, that they get on board with the best parts of populism and help facilitate them.

The worst case scenario, of course, is the opposite. That Republicans get behind the Trump agenda in its worst ways to support the President, but that new infrastructure is a bridge (pun intended) too far for them, while Democrats just try to stonewall everything Trump says or does, regardless of its value as a policy. This is why I get nervous about the way people on “my” side of the aisle are talking about Trump. Yes, many Trump supporters represent racist, sexist, backwards thinking. Yes, Trump has manipulated these people into getting into the White House. Yes, Trump himself is a horrible human being who, like Bill Clinton, has committed sexual assault and bragged about it. None of this means that we should oppose a Trump plan to build new high-speed rail in the US, nor a Trump plan that replaces the ACA with something better. We don’t know that he will propose any of those things, of course – it may all be smoke and mirrors. But if he does, we should be ready to support it. Even if he’s a loathsome individual personally.

And this relates to the other main concern I have about the disloyal opposition’s approach to attacking Trump. I fear that people see Trump as the problem with America, not a symptom of its problems. In focusing so much attention on Trump as a person, on Trump’s supporters, on the worst aspects of Trump’s proposed policy and Cabinet, we are ignoring what about Trump is a natural outgrowth and evolution of the road we’ve been on since 9/11. And that, I fear, is very dangerous. Because if we think Trump is the problem, much less the genesis of the problem, and not merely a symptom, then we will think we are cured whenever we move beyond Trump. And that means we might celebrate someone who is only a couple minor steps to the left of Trump as a wholesale solution.

Trump offers us an amazing opportunity to see what is wrong with us, in full view. It’s not that Trump is good, by and large, though I agree with him on infrastructure, the TPP, and not doing a lot of interventionist wars. It’s that so many people from all walks of politics can recognize that Trump’s hateful rhetoric is wrong. That so many can see his bravado and authoritarian love of displays of military might and his appeal to traditional white male domination, to the rule of wealth, that all of these things are horrible. They are horrible. We are right to stand up and attempt to shout them down.

But it is not really about Trump. It is about an America that has always championed these values, has always believed in wealth and power and corporations and white men at the expense of those people they oppress. About an America that has always been racist and sexist and homophobic. About an America that has a long, long way to go before it can be considered good, much less great. This is why the attack, the Clinton slogan, that America has always been great was both insidious and a losing strategy. It’s not true. America is a force for ill in the world and we need to work very very hard to try to steer that ship in a new direction. Blaming the captain who is maintaining course and only accelerating it has truth to it, but only partial truth. The whole truth is that we needed to crank the wheel, regardless of speed. Yes, accelerating is a bad plan when we’re going in the wrong direction. But as long as we’re going in the wrong direction, the speed is actually a secondary issue.

In this way, the likability of Obama and the obvious odiousness of Trump almost work against us. They confuse the issue. As do all the comments about decorum and dignity of the office. One of the very very few things I actually kind of like about Trump is that he can’t be bothered to make nice with all the establishment traditions and norms. This is what his supporters adore about him. The “ain’t nobody got time for that” attitude is refreshing in the face of a government that cares more about appearances than actually helping anyone. But of course, Trump’s odiousness goes far beyond firing off tweets that always speak his mind. It goes to sexism and crassness and dismissing people’s rights and some stuff that is very important and very bad.

In this context, Obama was a wolf in sheep’s clothing, or maybe a fox in sheep’s clothing, someone doing some really negative things with a lovable appearance. Trump, by stark contrast, is a wolf in wolf’s clothing. Or maybe a wolf in shark’s clothing, or T Rex’s clothing, the manifestation of a monster while his policies are perhaps just a little bit worse. By focusing on the costume, we avoid looking at the actual teeth, evaluating the actual danger. The danger is real with Trump, but it has always been real. We should not let the fact that Obama is smart and nice and looks the part get in the way of criticizing his failings. And we should not let the fact that Trump appears to be the devil incarnate get in the way of supporting the very few things he might suggest that are good.

And maybe there will be nothing. I am open to this unfortunate and scary possibility, that Trump is indistinguishable from Jeb, that he just saw an angle and a constituency he could galvanize and will then use his platform to aggrandize mainline Republican policies through and through. Or that he will make deals with the Republicans to those ends. I can’t imagine why the Republicans would have fought so tremendously hard to stop him if this were the case, but it could happen. Really, anything could happen. And in that uncertainty, we get the last piece of the puzzle that people hate about Trump. He’s unpredictable. They go to bed at night not knowing what will happen in the morning.

But change and hope and possibility depend on uncertainty. Maybe not Trump’s uncertainty, certainly. Maybe everything he does will be bad and awful and damaging. But with the fomentation of that uncertainty, there is real opportunity. Opportunity to enable Trump to show us the error of our ways, all of our ways, and chart a new course. Opportunity to accept and acknowledge anything Trump does that happens to be helpful. Opportunity, perhaps most importantly, to shift the landscape of how we view American politics, away from a bifurcated D and R and into a new road and new alignments that enable us to ditch time-honored traditions like murdering everyone who disagrees with us along with several wedding parties in countries where such people disagree.

It’s not much. It’s a cracked window opening, or perhaps a crack in a window. But it’s there and we can try to let a little light in as we steer the ship into rougher seas.