Reflections on Political Leadership and Legacy
Twelve years back, I penned my inaugural “Blue State Blues” column, centered around then-President Barack Obama’s tendency to lean on executive power instead of engaging with Congress.
I mentioned that Obama began his political journey in Chicago, feeling a strong connection to Harold Washington, the city’s first black mayor.
Washington, though elected with the backing of progressive reformers, faced significant pushback from fellow Democrats, particularly the white “ethnic” politicians who wielded power within Chicago’s political scene and resisted his initiatives.
When confronted with the “War of the Councils,” Washington sought to stretch the boundaries of executive power. However, the situation shifted when Representative Luis Gutierrez won a pivotal special election, granting Washington’s supporters a majority in Congress.
Unfortunately, it was too late. Washington suffered a heart attack early in his second term, which deprived him of the opportunity to wield the power he had gained.
The lessons for Obama were clear: political opposition can often arise from not-so-great motives like racism or corruption. Additionally, leaders need to act swiftly to utilize their power before circumstances change.
It’s no surprise Obama pushed Obamacare through Congress on a party-line vote—an overhaul of a health insurance system that struggled from the get-go and still relies on subsidization.
This urgency explains why he implemented Deferred Action for Childhood Arrivals (DACA) along with other unilateral amnesty measures. And there’s a reason he didn’t submit the controversial Iran nuclear deal for Senate ratification.
Obama came into office promising to heal the political divide in the nation and drive necessary changes, even if they were contentious. Yet, as Senator Joe Lieberman lamented, he missed an opportunity to pursue entitlement reform because he wasn’t seen as credible enough to do it. Instead, he fell back into familiar liberal patterns, pushing for his agenda using what he termed his “pen and phone.”
Democrats admired Obama’s almost autocratic style, while the Tea Party countered by reminding everyone of the constitutional checks and balances on executive power, a stance some Democrats criticized as “racist.”
These days, while Democrats join the “No Kings” protests against Trump’s perceived authoritarianism, his executive actions often received court endorsement, even before he appointed a significant number of judges aligned with conservative views.
It’s interesting to see Democrats aligning with the Tea Party in calls for a president who respects the Constitution. Still, their position isn’t fully genuine. The party just put forward a New York City socialist who aims to expand government control over various aspects, including food prices and education.
Many Democrats seem inspired by a utopian ideal of a flawless society, achievable only by consolidating government power and stifling dissent, much like how they’ve managed cities and universities.
On the conservative side, there’s a natural skepticism toward government and a preference to avoid intruding into others’ lives. We want autonomy over our own. Yet, now Trump appears to be reclaiming control, and his style—sometimes genial, demanding loyalty, encouraging flattery—doesn’t faze us. It reminds many of leadership styles in the business realm, where proactive behavior is often rewarded, and straddles boundaries.
If Obama is seen as America’s mayor, Trump seems to view himself more as its owner, akin to a family business. This mindset carries political and ethical risks, but it seems to be resonating, rekindling a connection between the government and its people that had faded over the years.
Obama also represented a “woke” ideology, suggesting American institutions were fundamentally flawed and needed to be reformed by a new elite. In contrast, Trump critiques this “woke” movement, reinstating ideals of nationalism and modernity to our political discourse. Both perspectives may not fully resolve our issues, but they’re crucial for moving forward.
A quick note: Around a decade ago, some of Obama’s early critics, our website’s founder Andrew Breitbart among them, foretold that conservatives might one day rally behind a celebrity like Trump.
Breitbart also recognized that Trump had a better grasp of voters and the media than many Republicans, a fact that positioned him as a potential savior during the Obama years.
Just before Trump’s surprising 2016 victory, a woman at a Florida rally commented on her belief that while Trump isn’t a saint, he serves as a divine instrument for America’s salvation.
If that’s true, it’s largely due to Breitbart’s efforts to confront Hollywood, the media, and Obama, which helped carve out an audience receptive to Trump’s message.
Trump isn’t a king; he’s a leader. Many Americans struggle to recognize that leadership because it’s been absent for so long. His authority doesn’t stem from wealth or charm, but from the backing of those who needed someone like him to challenge the complacency of the elite and reclaim control over their lives.
President Trump seems to be concluding the political narrative started by Obama. Following the trauma of 9/11, the fallout from the Iraq war, and the financial crisis, Obama had envisioned a “fundamental change” for America. Conservatives, however, are focused on “healing” the nation, finding a champion in Trump.
Radical elements persist in places such as New York, but the fact that many Democrats are endorsing the Constitution—as a tool of opposition—offers a glimmer of hope.
