LONDON—President Barack Obama cut his political teeth in Chicago. It’s fitting then that he chose that city to deliver his farewell speech as President, soon after its homicide rate hit a 20-year high under his watch. Chicago is a city traumatized by death. Obama is the man it raised up high in hope. “An Amazing Journey” for him it may well have been, but how amazing was it for everyone else remains a matter of debate.

The President’s approval rating comes in at a record high of 60 percent. As with all Presidents it is only set to continue rising with time. Though it is to his lasting legacy–not popularity–that we must turn, for these days even reality TV stars have proven popular. But legacy is the stuff of history.

From Blowfly’s 1988 satire First Black President to Nas’s 2008 track Black President, within my lifetime the idea of a black president has gone from laughable fantasy to serious reality. How important this is in historic terms to an integrated future cannot be understated. Clearly much remains to be done, although today’s equivalent of me in 1988–disenfranchised angry and radical–no longer has an iron wall segregating their imagination from the possible. The only visible role models I encountered back then were educated, articulate Islamist separatists. In this sense, President Obama’s precedent is an unquantifiable positive in legacy terms.

Obama’s evolution on equal marriage culminated in his 2012 affirmation that same sex couples had the right to be married. And though the decision was ultimately made by the Supreme Court, the President’s vocal support was undoubtedly crucial. With this one decision, millions of lives have been emancipated, but better yet is the millions to come who will experience true liberation: never to know what it felt like to be so stigmatized for their sexual orientation.

The number of Americans who believed climate change to be a top priority plummeted under Obama from 38 percent in 2007 to 28 percent in 2013. Against these odds, and with Republicans controlling both Houses, Obama managed to commit the U.S. to the Paris Climate Deal. This obliges the world’s nations to ensure the global temperature rise remains less than two degrees compared to pre-industrial times. If implemented properly, the Paris accords have the potential to herald the end of the fossil fuel era. The effect that erratic weather, rising sea levels and dwindling fresh water flows have on food supplies, migration patterns, and war makes this a truly magnificent achievement for our planet.

Talking of precedents, Obama’s term was a time for First Ladies to shine. Whatever your views on Hillary Clinton, it is hard to imagine any future First Lady being expected to serve as mere window dressing. And no First Lady has proven she has a right to be heard as well as Michelle Obama.

Granted, Michelle’s eloquence is not Obama’s achievement, but her prominence says much about the mood for gender equality under his presidency.

That view also shows in Obama’s only two appointments to the Supreme Court. Both were women. Elena Kagan and Sonia Sotomayor–the Court’s first Latina judge–tripled the number of female justices to three.

Yes, being female is no assurance of a good judge, just as being black is no guarantor for a good president. Glass ceilings should not be shattered for mere tokenism, but by people of merit. Talent should be accepted from wherever it hails. But with only one female supreme court judge, it was clear that talent was not coming from wherever. Rather, it was coming from a very specific somewhere.

To bring millions of people into healthcare was always going to be a difficult move. Obamacare is roundly unpopular, with voters. Even the majority of its supporters prefer it to be reformed. Its errors, and the backlash against it could be explained in part by its lack of cross party scrutiny and support.

From Civil Rights to the Patriot Act, most landmark pieces of legislation succeeded by appealing to both sides of the house. This ensures they were built to last. The Affordable Care Act should never have been a unilateral initiative. But even Republicans accept they cannot simply now cancel the act without presenting a reasonable alternative. The GOP anticipates a three year delay to guarantee that any replacement has longevity.

At least Obamacare has kickstarted a debate around more accessible healthcare. And even by Conservatives’ estimates it boosted health cover by 14 million people. That much at least is a good thing. Bank it.

Gun control would only ever have seemed achievable if tragedy struck. A series of incidents from Tucson, Arizona,, through Aurora Colorado, including the children at Sandy Hook, and culminating this month at Fort Lauderdale shook the nation. Sadly, even these multiple mass shootings were insufficient for Obama to be able to build the alliances needed to make this happen. His bill failed at Congress. So the President went as far as he could without Congressional approval, issuing an unprecedented 23 Executive Orders on gun control.

2016 was the year in which many icons breathed their last. Among those was the dictator Fidel Castro. By most accounts, Cuba’s human rights have gotten worse since Obama’s overtures. Any economic gains from increased trade with America go mainly to Cuba’s military regime. But business and tourist ties are now too deep to reverse. Cuba is less free than many places, but it is no Iran. Having economic mechanisms already in place will be crucial to any next stage of major reforms, tied explicitly to the U.S. embargo. Cuba’s Gorbachev cannot arise unless the foundation already exists for him or her to exploit. Amid understandable grumblings from older Miami-based Cuban dissidents, Obama may have unwittingly chosen a wise year in which to soften ties. Castro’s passing is the perfect opportunity for reformers–and the embargo is the perfect leverage to pressure for internal democratization.

That was the good. What remains is to consider the bad, and the ugly. So to adapt a line from that iconic movie, there are two types of men in this world: those who lead, and those who don’t. And there is so much in Obama’s legacy indicating his trouble with leadership.

The economic meltdown was perhaps Obama’s first major test in leadership. Appallingly, no senior banking mogul–those who lost billions, not millions–was ever held responsible for the crash, and major systemic change never came. A gratuitous bank bonuses system remained intact, and the U.S. government appeared to side with big business, even finding itself owning a car company after bailing out General Motors.

Leftwing anger catalyzed in the form of Occupy Wall Street, later fuelling the discontented who would “Feel the Bern”. More significantly though, as bitterness over bailouts provided the Tea Party its long awaited time in the sun this eventually gave way to the alt-right, creating Trump voters from traditional blue collar Democrats angry over lost jobs. “Too big to fail” was the overwhelming aftertaste of Obama’s timidity in the face of corporate America.

With white supremacist bloodshed and black nationalist killing, ironically, race relations plummeted under America’s first African-American president. As black on black crime soared in his home city of Chicago, and as community relations with police plummeted all over, the divisive politics of identity made an ugly comeback. And whether it was years of pent up aggression, latent racial tension or his mere presence emboldening hitherto pacified race-radicals, Obama cannot escape scrutiny.

Leadership was needed. Yes black lives matter, and so do blue. They are in fact codependent. The result of police feeling unable to do their jobs is more black deaths through street violence. Though not as a ratio, more in sheer numbers of American lives have been lost to street violence in Chicago than in Iraq and Afghanistan combined. This earned the city the moniker Chiraq, leading many to ask where is Obama?

In a sense, great leaders transcend the good and the bad. Every good thing they do affects millions, and every mistake can cost hundreds of thousands of lives. In this way, judging legacy is reduced to sifting consequential leaders from inconsequential ones. We try to determine whether those consequences were good or bad for us, in historic terms. But here is where it gets dark.

By ending World War II President Truman was among those who saved western democracy. To do so he ordered the atomic bombing of Hiroshima and Nagasaki, and killed over 130,000 people within four days. Likewise, no appraisal of Obama is complete without considering the near existential threat to world stability that the Syria crisis and its related rise of ISIS unleashed. And it is here that Obama’s “lead from behind” legacy will suffer terribly.

Back in 2003 aboard the USS Abraham Lincoln, President George W. Bush infamously declared that Iraq was a “mission accomplished”. In May 2011 President Obama declared that the United States had killed Bin Laden. Time was to prove that this became Obama’s very own “mission accomplished” moment.

Obama’s State Department approached the problem of jihadist terrorism as one would organized crime. As with Al Capone, the idea was: take out the leader and the organization crumbles. Such a false analogy could only be promoted by an administration that refused to acknowledge it was dealing with an ideological problem, not a criminal one. Obama’s administration worked diligently to ostracize reform Muslim voices warning of a global jihadist insurgency, and instead frustratingly restricted the problem to “al-Qaeda inspired extremism.”

In denial, they dogmatically refused to accept it was not al Qaeda that inspired extremism, but extremism that inspired al Qaeda. Stating on CNN at the time of Bin Laden’s killing that we ignore the power of the Islamist ideological “narrative” to our peril, I warned that the “real strategic threat” would come from the wider al Qaeda “franchise” and those “vying to replace bin Laden as symbolic leaders.” It followed that killing Bin Laden was seen as a victory for the organized crime model. Naturally then, Obama was totally blindsided by al Qaeda’s successor, the so-called Islamic State.

From day one Obama decided to abandon any semblance of ideological confrontation with Islamist theocracy. He famously couldn’t even bring himself to name the threat, instantly crippling any counter-propaganda effort. Enter the Voldemort Effect, where one is so petrified of evil that “Must Not Be Named” that the resulting policy comes to resemble ideological appeasement, except coupled with a presidential military power grab.

Of course, failing to name Islamist extremism from fear of stigmatizing Muslims, only further stigmatized Muslims. As I put it to Fareed Zakaria with Anderson Cooper, failing to name and distinguish this Islamist threat from Islam the faith would lead to the average American simply blaming all Muslims in frustration, while disempowering reform Muslims within the community by depriving them of a lexicon to isolate the Islamists from among them. Even former British Prime Minister David Cameron found himself openly correcting Obama on this weakness. Trump’s rise aided by anti-Muslim elements within the alt-right, eventually realized this fear. Once the ideological element is discounted, this only leaves the options of law and war. Obama went to town with both options.

As for law, Obama’s Justice Department invoked National Security to bully journalists in ways that would send shivers down your spine. Journalists working for the Associated Press were subpoenaed for their telephone records under the guise of National Security in order to track down a leak. Obama’s administration also investigated a Fox News reporter as a probable “co-conspirator” in another national security case so they could get at his email and phone records. And more often than all previous administrations combined they used the Espionage Act against whistleblowers who shared secret information with reporters.

As for war, in refusing to recognize the ideological nature of this problem, the Obama administration assumed that we could kill our way out of it. And so it was that drone strikes, and targeted killing rose more under this president than under any other in history. Preferring antiseptic warfare to difficult ideological conversation with Muslim communities, Barack Obama even devised a “Presidential kill list” assassinating individuals from afar–including American citizens–without Congressional oversight.

Just imagine if a Republican had done all this.

Nothing exemplifies Obama’s moral cowardice in challenging bad ideas, while preferring to try and kill them instead, than the rise of “blasphemy” attacks across the world.

This was brought home by the President’s chilling statement at the United Nations that "the future must not belong to those who slander the prophet of Islam”. In that speech, Obama conflated violence, misogyny, theft, racism (though race is not a choice, unlike religious ideas), hate speech (though targeting individuals for bullying is not the same as scrutinizing ideas), and discrimination (though singling out Muslims for exceptional treatment is not the same as satirizing the religious doctrine of Islam), with "blasphemy" (which must remain a prerequisite for liberal and scientific progress.) Even Galileo would have fallen foul of this test. And this is how by the time the Charlie Hebdo massacre occurred, freedom of speech had lost the moral custodianship of the world’s strongest democracy just as it needed it most, while illiberal authoritarianism was once again on the rise globally.

Naturally, as would happen in any insurgency, killing al Qaeda leaders while ignoring the ideological and social conditions that gave rise to them, only led to jihadism metastasizing. No wonder then that ISIS emerged to succeed al Qaeda and catch Obama’s entire administration entirely off-guard. This President cannot hide the fact that the worst terrorist group we have ever known rose under eight years of his watch. The buck stops with him.

But it gets worse.

Not only did the President admit to having no strategy to defeat ISIS, he remained non-committal. His staff named it the Obama doctrine: leading from behind. And nothing demonstrates Obama’s humiliation in Syria as much as Vladimir Putin and Hassan Rouhani calling his bluff over his “red line.”

The disastrous geo-strategic consequences of this lack of commitment will remain with us for decades to come. The Syrian refugee crisis, causing huge migration flows to Europe, is largely responsible for the rise of European populism and the potential break up of the European Union through Brexit. This all could have been avoided with early action in Syria, and early leadership. Instead the world looked on as America fell back into its great retreat.

All over the Middle East chaos, and Putin, moved in as America retreated. From Syria to Libya, Iraq, Yemen and the Sinai, states failed and jihadists multiplied. Yet as Bashar Assad dropped chemical weapons over his own people, Obama chose to strike deals with Assad’s main backer: the belligerent Iran, while effectively signaling to the world that Israel was the only problem that deserved special UN attention. In 2016, more UN resolutions were passed against Israel than Syria, North Korea, Saudi Arabia, Iran, and the potential genocide in South Sudan combined. Only liberal dogmatists could ever fail to see the sheer ludicrousness of such uneven treatment.

Obama did not expand his Presidency with a Trump in mind. Only a man who trusts himself more than he believes in the system, a man who always thinks he’s the smartest guy in the room would be oblivious to the dangers of doing such a thing. And only liberals totally enamored by their own man in charge, before any desire to protect the system and the country, could ever tolerate such a thing.

Yet this is precisely what happened. Locally and nationally, Democrats suffered their worst defeat since the 1920s. Both houses and the Presidency are now controlled by Republicans. And even Republicans will accept that the President-Elect is not just any Republican.

Trump is his own brand of crazy.

Now all those executive orders, all that antiseptic sanitized drone warfare from afar, all that NSA data collection, and yes that Presidential kill list, all that unprecedented executive power built up by an Obama who was unable to lead via Congress, and so needed to go it alone, now belongs to Donald Trump. Who do you blame for that?

Trump has promised to kill Obamacare with an executive order on day one. He is a climate change denier who is in danger of reversing any progress Obama made at the Paris Accords. He has threatened to undo the Cuba deal. And will reverse Obama’s progress on the Supreme Court in an instant, with an appointment of his choice.

Obama’s aloofness, his inability to lead, gave rise to his unilateralism. His is best described as an Imperial Presidency. Reigning through an uncharacteristic level of executive orders and military decisions shrouded in secrecy, but without broad cross-party appeal. Obama’s consolidation of presidential power created the perfect climate for an authoritarian figure to succeed him. The problem of course with any government that amasses power and asks you to trust them, is that the power remains even once the trust has waned. I even suspect that Trump will serve two terms.

Perhaps then, the most consequential legacy President Obama will leave us with is Donald Trump.