Now That's What I Call Losing! (Volume 1)

Throughout his campaign for president, Donald Trump put a "yuge" emphasis on the concept of winning. He complained in stump speeches that the United States "doesn't win anymore" and promised that, under his administration, "we're going to win so much. You're going to get tired of winning!" It was a bold statement, but one that makes a lot of sense when you look at what we know about the man. This is a person who based his entire public persona on being the best at everything he did. Every success was entirely his doing, while everything that could be perceived as a failure (and there have been plenty of those) was obviously not his fault. Trump University? Only an issue because the judge was biased against him. Losing the popular vote? Clearly there were millions of illegal voters skewing the numbers. It's clearly such a critical part of his psyche to be seen as the victor in everything he does.

With that being the case, one has to wonder how the president is mentally handling the first 67 days of his administration. Because, for a man who is so focused on winning, his time in the White House has been defined by a series of humbling losses. Let's run through some of the greatest misses of the Trump era in this first volume of "Now That's What I Call Losing!"

  • We begin the list with something that wouldn't have been considered a loss at all if Trump hadn't taken such great strides to define it as such. I am of course referring to his inauguration and subsequent claims that it was the largest and most-watched swearing-in ceremony of any president ever. What made that claim, which was provably and obviously false, so ridiculous was that no one cared except him! The first 72 hours of his administration could have been spent focusing on policy or settling in with the new administration; instead, Trump used that time to waste energy on a battle that did nothing but attempt to soothe his fragile ego.
  • The first major defeat of Trump's presidency came in the form of the judicial rejection of his first travel ban. The rollout of the executive order was a complete disaster, resulting in mass confusion at airports and the unlawful detention and rejection of legitimate visitors, immigrants, and refugees. On January 28th, just one day after the executive order was signed, judges in New York and Massachusetts temporarily blocked the ban. This was followed up on February 3rd, when a federal judge in Seattle blocked the ban nationwide and on February 9th when a federal appeals court ruled against reinstating it. Trump cried foul and promised to challenge the ruling, but he never did. Instead, the administration quietly went to work on a new ban that they hoped could pass legal muster (more on that later).
  • Just over three weeks into his presidency, Trump found himself having to deal with a major scandal in his cabinet. National security advisor Michael Flynn was forced to step down after it was revealed that he had lied to Mike Pence and others about contact with the Russian ambassador regarding the Obama administration's Russian sanctions. Trump was turned down by at least one top candidate to replace Flynn before finally filling the vacancy.
  • Days later, Trump's nominee for Secretary of Labor, Andrew Puzder, was forced to withdraw after it became clear that he didn't have enough support from Trump's own party to win approval. Puzder was brought down both by domestic abuse allegations and, more recently, the revelation that he had hired an undocumented immigrant and not properly reported her employment on his taxes.
  • One day after Trump's well-received speech to Congress (undoubtedly the biggest "win" of his presidency to date), another cabinet scandal broke. Attorney General Jeff Sessions found himself at the center of a political firestorm when it was revealed that he had spoken to the Russian ambassador several times during the campaign. This directly contradicted him statements, under oath, during his confirmation hearing that he never had contact with the Russians while a Trump campaign surrogate. Sessions ended up recusing himself from any investigations into connections between the Trump campaign and Russia, a decision that infuriated the president.
  • The Trump administration hoped to turn the page on this cacophony of cabinet catastrophes by revealing its new travel ban on March 6th. Trump and his staff clearly hoped that this slimmed down executive order, which was to go into effect on March 16th, would be better suited to handle any legal challenges. They were wrong. On March 15th, a judge in Hawaii blocked implementation of the ban. Hours later, a Maryland judge also blocked portions of the executive order. Adding insult to injury, both judges used Trump's own words on the campaign trail (particularly his call for a complete "Muslim ban") to support their decisions to halt the order.
  • Trump turned heads in March with an early-morning tweet storm in which he claimed that former president Obama had tapped his phones in Trump Tower during the campaign. The president gave no evidence for this assertion, which was eventually traced back to a known conspiracy theorist who was interviewed on Fox News. Trump's claim, which he has refused to retract or apologize for, was rejected by the leadership of his own party and eventually completely debunked by the head of the FBI. But before it was all said and done, he had seriously pissed off a major ally by having Sean Spicer claim that British intelligence had conducting this illicit surveillance.
  • While all of the above was occurring, Trump and his administration remained under a cloud of suspicion regarding ever-multiplying ties to Russia. By mid-March, four close Trump associates (Sessions, Flynn, former campaign chairman Paul Manafort, and former advisor Carter Page) had been forced to either step down or recuse themselves due to shady ties to Putin or his regime. The scandal came to a head on March 20th when FBI director James Comey and NSA director Mike Rogers testified before a congressional panel. While the intelligence duo could not provide much in the way of details during the open hearing, they did confirm the worst nightmares of the Trump administration: the FBI was actively investigating Russia's interference in the 2016 election as well as the possible collusion of American citizens in the Trump camp. The Russia scandal continues to grow; on Wednesday, it was revealed that the FBI has evidence indicating that associates of Trump did communicate with Russian officials, possibly to coordinate the release of hacked information damaging to the Clinton campaign. The results of the investigation remain to be seen, but at the very least, the whole ordeal has damaged the credibility of the president and his administration.
  • Finally, we have the coup de grĂ¢ce: the cataclysmic collapse of the Republican attempt to repeal the Affordable Care Act (ACA). I wrote at length about the numerous issues with the bill presented to Congress by House leadership and endorsed by the president, but even I didn't expect the complete and total meltdown we witnessed last week. Trump and Paul Ryan, despite having majorities in both the House and Senate, failed spectacularly in their attempt to deliver on a campaign promise central to the Republican platform for the better part of a decade. While the president undoubtedly made some effort to pass the bill, meeting directly with many members of the House caucus, his inexperience was clearly a hindrance. According to reports, Trump "didn't know, didn't care, or both" when it came to details of the bill, and he spent much of his conversations with representatives talking about the election and asking them what his margin of victory was in their districts. In the end, Paul Ryan was forced to face the press and proclaim that "Obamacare is the law of the land." And Trump, the self-proclaimed master negotiator who famously said on the campaign trail that "only I can fix" Washington, proved woefully unable to do anything about it. 

The early days of a presidency are historically determined by the achievements made in the first 100 days of the administration. The failure on health care means that Donald Trump will almost certainly reach that all-important mark without a major policy victory. He has been defeated on ACA repeal, stymied repeatedly on his Muslim ban, and overshadowed time and again by the investigations into his administration's ties to Russia. His approval ratings are historically awful for a presidency this young. And the road ahead does not look any brighter, as upcoming pushes for tax reform and immigration legislation (including the ridiculous border wall) promise to be even more divisive than repealing the ACA and members of his own party have already declared the president's budget to be "dead on arrival" in the legislature.

For a man who ran his campaign on winning, Donald Trump is losing. Bigly. And unless something drastic changes, the man who supposedly doesn't know how to lose will continue to find himself repeatedly exposed to the concept.