What happens when a chaotic campaign turns into a presidency no one thought would happen?
1. The Win That Surprised Everyone—Including Trump
Donald Trump’s victory in the 2016 US Presidential Election came as a shock even to his own team. Neither his campaign staff nor Trump himself seemed genuinely prepared to win. Throughout his campaign, Trump often told his wife, Melania, things would return to normal after November because he didn’t expect to win the presidency. His team had different post-election plans.
Most of Trump’s advisors saw the campaign as a stepping stone for future opportunities in media or politics. For instance, campaign manager Kellyanne Conway thought about pivoting into a television career after the election. Likewise, Trump toyed with launching his own network, capitalizing on the brand visibility his candidacy had provided.
This lack of preparation was evident after the surprise win, as many had no understanding of the regulations or scrutiny awaiting them in the White House. For example, Paul Manafort joined the campaign because he believed they had no chance of winning and thus wouldn’t face investigations into his gray-area real estate dealings. When victory landed unexpectedly, the entire team was left stunned, scrambling to figure out their new reality.
Examples
- Donald Trump assured Melania “things would go back to normal” post-election.
- Manafort joined on the premise there’d be no subsequent scrutiny.
- Kellyanne Conway aimed to leverage her visibility for a media career.
2. Internal Rivalries Split Trump’s Advisors
Once Trump transitioned from the campaign to the presidency, the unity among his team fell apart. Jared Kushner and Ivanka Trump, often referred to as “Jarvanka,” clashed with Steve Bannon on how the administration should operate and its policy priorities.
Bannon, hailing from the ultra-conservative Breitbart realm, aimed to push an agenda focused on economic nationalism, curbing China’s influence, and refusing to engage in Middle Eastern conflicts. On the other hand, Jarvanka sought to guide Trump toward a more globalist stance with attempts to mediate peace in the Middle East and strike balanced policy deals. These starkly opposing views repeatedly disrupted White House operations.
Their conflicts reflected deeper ideological divides. To add fuel to the fire, Bannon sarcastically dismissed Jarvanka’s influence, scoffing at the suggestion that Jared might become the next Henry Kissinger. This tension soon became characteristic of Trump’s administration—full of infighting, clashing visions, and little consensus.
Examples
- Bannon called Jared Kushner and Ivanka Trump “the geniuses.”
- Jared tried leveraging his ties with Israel's Netanyahu and Henry Kissinger in Middle Eastern diplomacy.
- Bannon pursued policies like barring Muslim majority countries from US entry.
3. Executive Orders Took Center Stage
One of Trump’s first hallmarks as President was his reliance on executive orders (EOs). Steve Bannon, in particular, saw this approach as a way to “shock and awe” the political landscape and bypass congressional negotiation. These orders became symbolic of Trump’s direct, often dominating leadership style.
The issuance of an EO targeting immigration—often dubbed the “travel ban”—demonstrated this strategy. Crafted hastily by staff inexperienced in policy writing, the ban led to turmoil at airports nationwide and sparked widespread protests. Yet, the administration saw the controversy as evidence of its power to dominate headlines and disrupt norms.
However, the reliance on EOs underscored the administration’s struggle to navigate traditional governance structures. This pattern persisted, reinforcing the image of a presidency defined more by impulsivity than careful planning.
Examples
- Bannon planned to issue 200 executive orders within the first 100 days.
- The immigration EO banned entry from majority-Muslim countries, causing chaos.
- Staff searched online for EO templates showing a lack of procedural expertise.
4. Chaos Reigned Between Competing Factions
The early months of Trump’s presidency revealed the extent of the chaos within his White House. Jared Kushner and Ivanka Trump tried to present themselves as moderating influences over Trump, while Steve Bannon relentlessly pushed a hard-right agenda. Neither strategy fully controlled Trump, who veered unpredictably depending on who had his ear last.
One moment of clarity came when Gary Cohn and Dina Powell joined the administration under Kushner’s encouragement. Known for their connections to Goldman Sachs, they worked on a speech designed to present a more measured and “presidential” Trump. For a fleeting instant, their approach seemed to succeed.
Yet, this momentum was short-lived as Trump oscillated between adhering to scripts and unleashing extemporaneous rants that left advisors frustrated. The inability to strike a consistent tone showcased the deeply fragmented decision-making at play.
Examples
- Kushner and Ivanka pushed a more restrained style for Trump.
- Steve Bannon criticized a scripted speech as being too conciliatory.
- Infighting between “Bannonites” and “Jarvankaists” dominated White House dynamics.
5. The Russia Cloud Loomed Large
The investigation into Trump’s ties to Russia became a key turning point in his presidency. When details from the Steele Dossier emerged in January 2017, it raised the unsettling possibility that the Russian government held compromising information on Trump. FBI Director James Comey’s inquiry into these allegations only intensified, much to Trump’s dismay.
In May 2017, at Kushner’s persuasion, Trump decided to fire Comey. This act was widely criticized and interpreted as an attempt to obstruct the investigation. Predictably, it backfired. Deputy Attorney General Rod Rosenstein retaliated by appointing Robert Mueller to conduct a special counsel investigation.
The firing marked a major miscalculation, demonstrating Trump’s impulsive tendencies and his tendency to undervalue legal and political counsel.
Examples
- The Steele Dossier brought allegations of Russian kompromat on Trump.
- Kushner suggested firing Comey to halt inquiries into Trump family finances.
- Robert Mueller was appointed, escalating scrutiny of the administration’s actions.
6. A President Who Doesn’t Read
Trump’s aversion to reading has shaped his presidency in peculiar ways. Staff members observed that he struggled to process written reports and relied heavily on verbal briefings or television news to form opinions. Some speculated he might have a reading deficiency like dyslexia, but no concrete answers emerged.
This limitation led to several awkward missteps. For instance, when confronted with a chemical attack in Syria, Trump was initially dismissive. Only after viewing video footage showing the attack’s human toll—compiled by Ivanka’s team—did he agree to retaliate with a missile strike.
While unconventional, this visual-based decision-making highlights the challenges of operating a government without traditional information-processing tools.
Examples
- Hope Hicks provided Trump with pre-digested news summaries each morning.
- Briefings with complex PowerPoints irritated Trump.
- Video of the Syria attack convinced Trump to launch missile retaliation.
7. Mishandling Scandals and Twitter Rants
Rather than mitigating controversies, Trump often fueled them through impulsive tweets and poorly thought-out actions. His decisions during the 2016 Trump Tower meeting scandal exemplifies this. When news broke that Trump Jr. had met with Russian officials to gain damaging intel on Hillary Clinton, Trump crafted an unconvincing alibi about “adoption policies.”
Elsewhere, Trump’s infamous Twitter spats consistently undermined his administration. From attacking political opponents with off-the-cuff insults to making inaccurate claims, these rants sparked fresh waves of criticism.
Such behavior frustrated senior staff but remained a staple of Trump’s messaging strategy, painting a picture of a leader unwilling to rein in his impulses.
Examples
- Trump attributed the Trump Tower meeting to “discussing adoptions.”
- Twitter attacks targeted Mika Brzezinski of Morning Joe.
- Impulsive tweets regularly contradicted White House talking points.
8. Self-Sabotage Defined His Presidency
Whether in interviews, tweets, or policy moves, Trump repeatedly shot himself in the foot. This tendency became painfully evident during his July 2017 interview with the New York Times, where he inadvertently expanded Mueller’s investigative scope by openly discussing family finances.
Trump’s inability to stick to prepared scripts further undermined his credibility. For advisors like Steve Bannon, Trump’s lack of discipline became a source of endless exasperation, contributing to Bannon’s eventual firing by August 2017.
Trump’s penchant for self-inflicted wounds demonstrated how personal grievances often overshadowed effective strategy.
Examples
- Trump crossed legal lines by discussing Mueller’s limits in his Times interview.
- Bannon described him as the “most undisciplined politician ever.”
- Disagreements over self-promotion led to Bannon’s dismissal.
9. A Dysfunctional Administration
Ultimately, Trump’s presidency epitomized disorganization and competing agendas. With advisors vying for influence and the president’s own erratic tendencies at play, the administration continually courted controversy and inefficiency.
Bannon ultimately predicted that Trump may not survive his first term or secure re-election. His gamble on chaos had yielded a uniquely tumultuous presidency, with little confidence in its long-term success.
Examples
- Infighting between advisors defined the administration.
- Chaos expanded as scandals piled up.
- Bannon estimated Trump’s impeachment odds at 33.3%.
Takeaways
- Avoid impulsive decision-making by relying on a balanced team and informed strategies.
- Ensure strong organizational structure prevents internal power struggles derailing leadership.
- Develop clear communication channels to avoid missteps in high-pressure situations.