I was never an Obama fan, for reasons proven out over time. But when he won in 2008, I told some of my friends working on the campaign, "Good" and was sincerely not upset. They seemed shocked knowing my politics, but I explained that Truman lead to Eisenhower, Johnson lead to Nixon, Carter lead to Reagan, and Obama would definitely result in the huge Republican/Conservative backlash. If you want to destroy Democrats/Progressives, just give them everything they ask for -- and the public will be horrified. The lash will lead to backlash, and Obama was likely to result in a conservative revival the likes the world hadn't seen in generation. They were scornful at the time, and while I thought he would only be a one term President, it still proved completely prescient and almost embarrassingly obvious.
Obama had one history, and his past completely clashed with his campaign, and either was sort of a win. Let's call them realObama (Obama from his books and "accomplishments") and fakeObama (what the Campaigner promised). RealObama was an unaccomplished divider that slacked into our best colleges on an affirmative action ticket, and varied from completely forgettable in Columbia, to popular but unremarkable in Harvard, community organizing, or Illinois Senate, and he'd only parlayed that in the national senate based on being a pawn to the most questionable associates in the dirties state that almost always ranks dead last. FakeObama was this confidence artist offering the impossible: fixing our healthcare without it costing a dime in deficits, spending trillions on social programs while balancing the budget, all while promising to be a loving uniting moderate force-feeding radical reform on everything, without upsetting anyone.
- If realObama governed, he was going to going to be an inept and forgettable President (a community organizer) that pushed too hard on the wrong things using a cult of personality instead of competent policies, that would made things worse, alienated the other side, deadlock everything, and he'd burn out quickly, and be nothing but an empty chair. The consequences of his policies would quickly be erased/fixed by the next guy as they became another "new deal" that had no hope of succeeding more than the last 3 had, and he'd teach a generation the hard lessons of progressive overreach.
- If fakeObama governed, he was going to be a second term Bill Clinton moderate, who wouldn't do or hurt much (and stood a better chance of handing the reigns to another Democrat), but that moderate centrist also wouldn't be the radical change agent or be able to deliver a fraction of what he promised... and that would teach the generation that over-hype and over-promises of the left were nothing but hot air in an empty chair.
- Or of course, some combination of both.
So I sort of knew or at least suspected that America would get nothing but Jimmy Carter in blackface. None of his ideas were that new: they all sounded like what Carter promised/did, and didn't work. A prettier face and a little more charm than Carter wasn't going to change his destiny to lose a fight with a swamp rabbit of his own making. He seemed way too self absorbed to be able to make a good history, and he had no long term friends or allies of any repute to show he could build relationships, let alone relationships across party lines. So he didn't disappoint me, just all his followers.
- His Books - questionable authorship, and lies about his history (both in the book and campaign)
- His wife's payola at the University
- Questionable associate:
- Hillary Clinton - Secretary of State - corrupt fucking disaster.
- Eric Holder - Background, Fast and Furious
- EPA: Lisa Jackson - Background, 
- Sebelius: demands payment, violates the Hatch Act
- The great uniter: fakeObama ran on being a great uniter, "No Red America, no Blue America, just the United States of America". That sounds great, I would have loved that guy. However realObama was a community organizer (just one step up for an union organizer/agitator). His whole life had been made of anger/inflame/agitating people into demanding change for his political gain. His brief Senate career had him accomplishing nothing but blowing up deals and irritating the other side. He came in with race relations good, left with them far, far worse. America was looking for a less polarized America, and left with the parties in the greatest divide since the civil war. The left took no responsibility for any of it -- but Trump was the antidote to Obama. Instead of a smooth talking liar politician and man of inaction, they wanted a raw, truth telling (even if overstated) crass fixer that would just tell you what he was going to do, and then do it.
- Race relations: One of the key reasons he was elected was to improve race relations. It was 65% positive before he took office, and he left with it below 20%. His highlight include his handling of Trayvon Martin and George Zimmerman, like his speech That's President Racist to you. There was his sympathies for dividers like Black Lives Matter, his fuck-up with Gates arrest (having nothing to do with a President, and he made everything worse). There was Ahmed Mohamed (Clock Boy), where he thanked a Muslim kid for a prank of making something that looked like a briefcase bomb, and wasting the public's money on lawsuits that are later dismissed. 
- Obama on Energy: Ran as an "All of the Above" President, governed as an anti-energy buffoon, from his Keystone Pipeline obstruction for 8 years, solar Subsidies that went bankrupt like Solyndra and a dozen other companies that went bankrupt on the taxpayers dime.
- Obama’s post-partisan timeline - Obama ran on being a great uniter, ("No Red America, no Blue America, just the United States of America) -- but he was the great divider instead. What do you expect from a community organizer (or a DNC progressive) whose job is to anger/inflame people for political gain? The left will of course take no responsibility and blame the other side, but if you compare his couple years in office to George Bush's, Obama was far more divisive, polarizing, partisan, and set the tone for the later claim by Republicans that, "we need to make him a one-term President".
- Privacy/Spying: Ran as against FISA (going to eliminate it), and be the most transparent administration, eva. Did the opposite. Not only didn't he eliminate the Patriot act, he expanded it, FISA warrants, and abused powers around it. He spied on the AP, spied on Americans (NSA), spied on the Press - Rosengate, spied on his political opposition (Trump) and the IRS targeted his political opponents.
- Injustice is the new justice: his oath is to protect the constitution and law of the land. Instead of being Law and Order, he abused power (executive orders) often to dilute or undermine laws he didn't like -- not through proper means (Campaigning and pressuring Congress to fix/legislate them, but to circumvent them). NOTE: I don't like a lot of these laws, but there's a right way and wrong way to fix them. He chose wrong, every time. From Immigration, DACA, Drugs, EPA doing "sue and settle" to extending regulations. There were Corruption/Graft/Payoffs, AKPD payoffs, Sestak bribe, ACORN, Pigford scandal, VA scandal, porkulus payoffs (bail outs). He diminished the Justice Department credibility when they used a racial double standard in failing to pursue a voter intimidation case against Black Panthers menacing voters at a polling place in 2008 in Philadelphia.
- Obamacare/ACA - ran on mocking Hillary Clinton's idea of a mandate, and promised to be a bipartisan -- then literally locked the Republicans out, mocked them, implemented a disaster with questionable procedure, put in the mandate that he mocked, lied that it was similar to RomneyCare or the Heritage Plan (it wasn't), and then got caught in 29 public lies about Obamacare (like 'you can keep your doctor', 'we won't force people to pay for abortions', he was against mandates before he was for it). Then gave Obamacare Waivers to donors (over 1,200): ideas so good, that donors could buy their way out of them.
- 🤥Death Panels - Republicans (and Sarah Palin) started using the term "Death Panels" to describe part of the ACA, where a panel of 15 oligarchs could make life and death decisions over what treatments would be covered or not (to control costs). The far left all called that untrue (Politifact called this the lie of the year in 2009), but accounted for the savings these panels would bring by denying care. Then they screamed again when those panels (that never existed) were eliminated in 2018.
- Budget - blew up budget deals which caused the government shut-down, blamed the other side, then spent extra money to close monuments/parks during "shut down" to increase the public harm (and pressure his opponents).
- Nobel Peace Prize - Obama was awarded it for not being George Bush, and campaign promises that he broke. A humble, gracious, or wise President, would have turned it down and said, "if you want to give it to me after my Administration's accomplishments, I'll accept". But Obama lacks those qualities, and there's the greed of wanting the $1.4 million that went with it. The Nobel Committee regretted the move after Obama invaded Libya, screwed up Syria, Iraq and Afghanistan, assassinated Saddam on foreign soil, lead to the invasion of Ukraine and the rise of ISIS, and became the biggest user/abuser of drone strikes in history.
- Bowgate - Obama was told by State Dept that it's an insult to bow as the head of state, so he did it 8 times, each time generating more cries from those who understood manners.
- HiroshimaGate - Japan's foreign minister asked Obama NOT to go to Hiroshima, so he did anyways. The reason was because either it made Japan lose face (for reminding them of their loss over starting the war), or it made the U.S. loses face as it would be seen as an apology for ending it. Bad optics. He ignored them, and magnified the slight by exclaiming in a speech on the site, "the war grew out of the same base instinct for domination or conquest that had caused conflicts among the simplest tribes." Whether Obama meant Japan or the U.S., it was an insulting oversimplification towards History, America, Japan, or all of the above.
- Russiagate - Obama was behind or involved in much of the whole fuck-up around Russiagate. Everything that could be handled poorly, was. Ignoring Russian hacking for 8 years, overreacting at the end, admitting our elections couldn't be corruptible from the outside -- and then changing his claim to divide us, spying on the opposition party with illegal or even missing FISA warrants that he promised to eliminate during his campaign.
- Libya /Benghazi - After promising not to invade/attack any country that wasn't an immediate and direct threat to the U.S., and after Gaddafi had given up his WMD programs and was helping us on the war on terror, Obama administration broke both promises and attacked Libya without provocation, to "prevent a human catastrophe", that the islamic extremists might not take over and destabilize the country, which is what he wanted or at least got in an al Qaeda controlled state (and weapons, instability and refugees that permeated the region). We can debate the nuances of legality around the War Powers Resolution, but the point is that Obama/Democrats/Media criticized Bush (who actually followed it) -- but then ignored Obama for ignoring it, after campaigning on being better. Just pick one standard please. Then there was:
- The failure of administration to protect the Benghazi mission (after multiple pleas for more security)
- Lying to the public about what happened: changes made to the talking points in order to suggest the attack was motivated by an anti-Muslim video, while knowing better.
- Opacity: the refusal of the White House to say what President Obama (or Hillary) did the night of the attack
- American Political Prisoner: arresting Nakoula Basseley Nakoula for "the fake video" that they blamed, to get attention off of them -- when they knew the video had nothing to do with it -- and throwing the book at someone to distract from it, is something that tin-hat dictators do. 
- the failure of the redline
- the rise of ISIS
- Russia/Ukraine - ignoring Bush's sanctions/warnings for Russia invading Georgia, the Obama administration started with a "Reset Button", because Putin was a trustworthy guy. He got caught telling President of Russia that he would be more flexible at looking the other way, and called Romney "stuck in the Cold War" for warning about Russia during 2012 campaign. So Russia invaded and annexed part of Ukraine, shot down a civilian airplane, tried to blame it on the other side, and then ignored the Budapest Memorandum -- a Bill Clinton (circa 1994) agreement that if Ukraine gave up Nuclear Weapons then we'd protect them from hostile neighbors (Russia) invading them. Obama sent them blankets, Trump later sent them weapons and anti-tank missiles, and the left calls Trump soft on Russia.
- Iran Nuclear Deal - After Obama showed fecklessness on Syria and Ukraine, he negotiated with the Mullah's in Iran. Basically, we'd give them billions of dollars cash, terrorist prisoners, remove sanctions, and the Iranian Regime (caught in multiple lies), agreed to continue to develop missile technology, but reduce their centrifuge production temporarily -- but we could only verify that in a few locations (most of the country would be off limits), and only if we gave them enough advanced notice before inspections.
- Expended no energy on American Hostages abroad (unless they turned out to be-anti-American deserters). Like Otto Warmbier: kid caught trying to steal a propaganda poster from North Korea, and was tortured, brain damaged, and sent home to die soon after. Individuals are expected to sacrifice for the greater good, in the Obama world view.
- Most Presidents have the good manners to step out of the spotlight and let others lead. Well, other than Jimmy Carter, but in degrees of incompetence, he's in rarified air. But Obama keeps jumping into events that have nothing to do with him and saying, "don't forget about me!", like pictures of himself remembering Steven Hawking or Rosa Parks. He's like the Brian Williams of ex-Presidents trying to prove he was there. 
- He keeps offering to campaign with Democrats to "help them", but they keep turning him down. Even hard-core lefties know that there's a lot of ugly tied to his regime, and they'd rather run solo, that be coupled to his administration.