Was Trump’s election actually Obama’s masterstroke?

Does this guy looked worried?

Let’s go back to late July of last year. President Obama and his team are in the Oval Office, busily preparing his keynote speech for the upcoming Democratic National Convention. For the first time in his presidency, Obama is starting to seriously consider his legacy.

What does Obama’s team know at this point?

  • They know that Donald Trump, the Republican nominee for president, is not to be taken lightly in November’s election. Internal polls suggest a strong anti-establishment mood. Trump has already pulled ahead of Hillary Clinton, the Democratic nominee, thanks to a bounce from the previous week’s Republican National Convention.
  • They’ve heard early rumblings from the intelligence community — via the Steele dossier and other channels — about Trump’s compromise by FSB, Russia’s main security agency.
  • They know that the bull market in equities, which started in March of 2009, is long in the tooth. They’re familiar with the stock market fumbles that typically greet the end of a two-term presidency.

Knowing that the president’s legacy (including the fate of Obamacare) hangs in the balance, the team decides to read the tea leaves of what a Clinton victory and a Trump victory will look like.

Forecasting a Clinton victory

With Clinton in the White House and the GOP in charge of the Senate and House of Representatives, political gridlock continues to be the name of the game. As promised by Senator John McCain, the Republicans continue their unprecedented obstruction against the new president’s nominee for the open Supreme Court seat. Given the president’s veto power, Obamacare continues to escape repeal.

With two years of Clinton investigations planned by Jason Chaffetz, the Chairman of the House Committee on Oversight and Government Reform, the GOP and the right-wing media go into full-scale attack mode against the president. Every day brings another drumbeat about Clinton’s email server or Benghazi or the talking point du jour.

As the economy stumbles in 2017 and 2018, the anti-establishment fervor that nearly cost Clinton the election only intensifies. Clinton’s infrastructure plan proposed in response to the slowdown is dead on arrival in Congress.

Facing failure on the domestic front, Clinton attempts to burnish her foreign-policy credentials by ratcheting up the fight against ISIS within Syria. To the surprise of nobody, US troops find themselves in a quagmire against a shifting enemy.

With an energized Republican base and the Democrats staying home in the midterm elections, the GOP strengthens its control of the House and Senate in 2018, though not enough to overcome the two-thirds majority vote required to override a presidential veto.

After twelve years of a Democratic president and a decade of political gridlock, the public yearns for something new. Clinton loses her reelection bid in 2020 to Paul Ryan, the popular Speaker of the House.

Taking total control of the federal government in 2021, the GOP dismantles Obamacare, confirms a staunchly conservative Justice to the Supreme Court, and enacts President Ryan’s agenda of harsh austerity measures.

Forecasting a Trump victory

With an almost comical disinterest in governing, Trump stumbles badly from the get-go. Steve Bannon, Trump’s chief strategist (who happens to be a white nationalist), acts as a shadow president, setting Trump’s agenda and communications strategy.

Early indications are that the new president is as advertised, with his seeming embrace of white nationalism, his autocrat-inspired war on facts, and his penchant for kleptocracy. Outraged by what they see, once-dispirited liberals take to the streets to protest. Just as pro-Obamacare Democrats faced angry town hall meetings in 2009 and 2010, Republicans looking to replace Obamacare without an adequate replacement are met with angry mobs, some of whom need the ACA to survive.

Trump nominates a conservative to fill the Supreme Court vacancy. Despite grandstanding and filibustering over what they see as a stolen seat, the Democrats have no way of winning the fight against the nomination.

The intelligence community, antagonized by the new president, leaks more and more about Trump’s illegal and dangerous ties with Russia. As the Russia scandal grows each day, calls for impeachment reach a fever pitch. In the meantime, the GOP-controlled House and Senate use Trump as a vessel for enacting their anti-tax, anti-regulation platform.

With impeachment hearings looming, Bannon picks a fight with Iran, with whom he sees a conflict as inevitable. Sick of seemingly endless war since 9/11, the American public largely disapproves of this antagonism.

After Trump’s impeachment in 2017, Vice President Mike Pence becomes the new Commander-in-Chief. The pro-corporate agenda started under Trump continues in earnest under Pence. However, attempts to repeal Obamacare are seen as politically suicidal. Changes to the ACA are made on the margins.

Facing strong economic headwinds (including a rising rate environment) and a pissed-off electorate, the Democrats win back control of both chambers of Congress in 2018.

Over the next two years, voters become more and more disgusted at the inadequacy of the enacted austerity measures in combatting the economic slowdown. With the Republican brand now toxic, Elizabeth Warren is elected handily in 2020.

Starting in 2021, President Warren and the Democratic Congress build on top of Obamacare to work toward a single-payer, Medicare-for-all healthcare system.

What does Obama do?

I believe that Obama, seeing these two alternative realities, may have chosen to put his weight behind the Trump option.

In either case, the Supreme Court nominee would probably be a lost cause. Replacing Justice Scalia with a Scalia clone is essentially breaking even.

Electing Clinton would have supercharged the political pendulum to the right, putting Obama’s key achievement of healthcare reform in serious jeopardy while also doing major damage to the Democratic brand.

On the other hand, electing Trump (and eventually replacing him with a bona fide Tea Partier) would, counterintuitively, allow the core elements of Obamacare to be saved and improved. Despite their best attempts to distance themselves from Trump, the Republicans wouldn’t be able to escape the stink of Trump’s treason and incompetence. Seriously wounded from the presidency of George W. Bush, the GOP would essentially die off as a national party. As the country gets younger and browner by the day, demography would essentially force the party to make drastic changes to the middle and allow Democrats to govern from the left.

How does Obama do it?

There were a number of ways, from the subtle to the heavy-handed, for Obama to sabotage Clinton behind the scenes.

Most visible is Clinton’s email investigation. The FBI was never a fan of Hillary Clinton. Knowing this, Obama could easily have put pressure on James Comey, the Director of the FBI (and an Obama appointee) to make the unprecedented move of publicizing “new” details in the email investigation just 11 days before the election. As confirmed by Nate Silver, this one act almost certainly swung the election in Trump’s favor by influencing late-deciding voters.


We’ll know more in the coming years whether Trump’s election was actually an awakening of American liberalism or just another disastrous presidency in the mold of Richard Nixon and George W. Bush. Or maybe it’s both. Or maybe the deep state is really pulling the strings and all of this is just theater while our society built on massive debt and constant distraction crumbles slowly around us. Stay tuned!