Day 49: Trump’s Inner Circle – The Convicted Criminals

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Aesop famously said:
“You can judge a man by the company he keeps.”

While Project 2025 outlines an ambitious and public vision for reshaping America, Trump’s inner circle reveals a much darker picture.

These are the convicted, the extremists, and the disruptors – men who continue to support Trump, not with policies laid bare, but with underhanded tactics designed to undermine democracy from within. Today, we focus on the “convicted criminals”: Steve Bannon, Roger Stone, Rudy Guliani, and Michael Flynn – men who have been convicted of crimes yet remain integral to Trump’s operation.

But why is examining the people closest to Trump, a known narcissist, so important? Trump’s pathology thrives on loyalty and flattery, and he tends to surround himself with individuals who echo his own worldview rather than challenge him. These men know how to play Trump’s ego, whispering promises of unchecked power, populist revolutions, and dismantling of the “deep state.” As narcissists are highly susceptible to the influence of those who affirm their greatness, these individuals are not just advisors – they become extensions of Trump’s will.

While Project 2025 lays out a clear, albeit terrifying, agenda for reshaping America under conservative principles, the figures in Trump’s inner circle operate in the shadows. Their agendas are not about conservative governance but about subverting democratic norms for personal gain.

Unlike Project 2025, which seeks to reshape institutions from the outside in, the men surrounding Trump work from the inside out, manipulating public opinion and undermining democratic structures. They have no interest in policy debates or constitutional fidelity. For them, victory at any cost is the only goal.

This blog will examine four convicted criminals who have shaped Trump’s worldview. I will examine how Trump’s mafia-like inner circle works in tandem to influence not just Trump but the American political landscape.


Steve Bannon

Alias: The Strategist
DOB: November 27, 1953 (currently 70 years old)
Affiliation: Former Chief Strategist in Trump Administration (January-August 2017), Far-right Nationalist

Views on Democracy:
Steve Bannon has made it clear that he views democracy as inherently flawed and corrupt. His infamous desire to “deconstruct the administrative state” shows his contempt for the way modern democracies operate. Bannon believes that populist revolutions are the only way to disrupt what he sees as entrenched elites who dominate political institutions. He has repeatedly stated that conflict, not consensus, is the way forward, advocating for a more authoritarian, centralized style of governance.

Why Trump Trusts Him:
Bannon’s ability to channel the anger and frustrations of disenfranchised voters aligned perfectly with Trump’s campaign narrative. Bannon’s media expertise and ability to manipulate public sentiment through misinformation also made him an indispensable asset to Trump’s political operation. His vision for a populist uprising resonated deeply with Trump’s anti-establishment rhetoric.

Bannon’s Impact:
Bannon is a key figure in modern right-wing nationalism, heavily influencing Trump’s 2016 victory. As the head of Breitbart News, Bannon amplified voices that would typically be marginalized, stoking racial divisions and emboldening extremist views. His three major impacts include:

  • Breitbart’s Rise: Under Bannon’s leadership, Breitbart became a platform for white nationalists and far-right figures.
  • Immigration Policy: Bannon helped shape Trump’s harsh immigration policies, including the Muslim travel ban.
  • Voter Fraud Campaigns: Bannon has been instrumental in spreading false claims of voter fraud, which culminated in the January 6th insurrection.

Modus Operandi:
Bannon’s political tactics revolve around creating chaos and discrediting democratic institutions. His media strategies are designed to pit people against traditional governing structures and elevate far-right nationalist ideologies. Even after his criminal conviction, Bannon continues to use his influence through his podcast, where he mobilizes Trump’s base against perceived enemies of their movement.

Criminal Behavior:
Bannon was charged with defrauding donors in the “We Build the Wall” campaign and was later pardoned by Trump before trial. In 2022, he was convicted of contempt of Congress for refusing to comply with subpoenas related to the January 6th investigation.


Roger Stone

Alias: The Dirty Trickster
DOB: August 27, 1952
Affiliation: Longtime Trump Advisor, Political Operative

Views on Democracy:
Stone has a disdain for traditional democratic processes, which he sees as barriers to achieving his political objectives. His history of employing “dirty tricks” to influence elections and his willingness to embrace misinformation and conspiracy theories demonstrate his belief that democracy can be bent to suit personal or political needs. Stone thrives on the manipulation of public opinion, often prioritizing his own or Trump’s interests over democratic norms and the rule of law.

Why Trump Trusts Him:
Trump trusts Stone because of his long-standing loyalty and ruthless political strategies. Stone’s dedication to doing whatever it takes to win, whether legal or not, is an approach Trump admires and uses in his own political dealings. Stone’s history of manipulating the media and undermining opponents makes him an invaluable ally.

Stone’s Impact:
Stone has been involved in numerous campaigns that have undermined the legitimacy of American democracy. His notable impacts include:

  • Nixon’s Dirty Tricks: Stone’s early career in the Nixon administration shaped his view on how political sabotage can win elections.
  • 2016 Election & WikiLeaks: Stone’s role in coordinating with WikiLeaks during the 2016 election to release damaging information about Hillary Clinton was central to Trump’s victory.
  • 2020 Election Fraud: After his pardon, Stone played a key role in spreading false claims of widespread voter fraud, helping to fuel the January 6th insurrection.

Modus Operandi:
Stone operates as a political provocateur, leveraging media manipulation, disinformation, and alliances with extremist groups to push his agenda. His willingness to push baseless conspiracy theories, including those related to the 2020 election, makes him a dangerous figure in Trump’s circle, undermining the very foundations of democracy.

Criminal Behavior:
Stone was convicted in 2019 for obstruction, lying to Congress, and witness tampering during the Mueller investigation. He was sentenced to 40 months in prison but was later pardoned by Trump, a clear sign of their close alliance.


Rudy Giuliani

Alias: America’s Mayor
DOB: May 28, 1944 (currently 80 years old)
Affiliation: Former Mayor of New York City, Former Trump Personal Attorney

Views on Democracy:
Giuliani has increasingly embraced anti-democratic tendencies, particularly since joining Trump’s legal team. Once praised for his leadership after 9/11, Giuliani’s reputation has been tarnished by his participation in Trump’s attempts to overturn the 2020 election. He has supported conspiracy theories that seek to undermine democratic institutions and spread false claims of voter fraud, showing a blatant disregard for the integrity of the democratic process.

Why Trump Trusts Him:
Trump trusts Giuliani because of their long-standing relationship and Giuliani’s fierce loyalty. As Trump’s personal attorney, Giuliani was instrumental in shaping the legal challenges against the 2020 election results. His willingness to defend Trump at any cost, even as it led to his own legal troubles, solidified his place in Trump’s inner circle. Giuliani’s aggressive and often reckless legal strategies mirror Trump’s own disregard for norms and laws.

Giuliani’s Impact:
Giuliani’s influence on Trump’s presidency and post-election efforts has been substantial. His notable impacts include:

  • Trump’s Personal Lawyer: Giuliani led the legal charge in efforts to overturn the 2020 election results, spreading false claims about voter fraud, rigged machines, and illegal ballots. His public statements and court filings helped fuel conspiracy theories that culminated in the January 6th insurrection.
  • Ukraine Scandal: Giuliani played a pivotal role in the Trump–Ukraine scandal, where he attempted to pressure Ukraine into investigating Joe Biden, leading to Trump’s first impeachment.
  • Role in January 6th: Giuliani spoke at the rally preceding the Capitol riot, encouraging the crowd with calls for “trial by combat,” directly inciting the events that followed.

Modus Operandi:
Giuliani’s method has always been to push legal boundaries. From his days as a U.S. Attorney prosecuting the Mafia, he reveled in high-profile cases and dramatic flair, often stretching legal tactics to their limits. Since becoming Trump’s personal lawyer, Giuliani has adopted similar methods, stoking chaos and conspiracy theories through media appearances and baseless legal filings. His disdain for democratic norms, once masked by his mayoral success, has become all too clear in his efforts to overturn the 2020 election.

Criminal Behavior:
Giuliani has faced multiple legal challenges, including a 2023 indictment related to the Georgia election racketeering case. He has been accused of making false claims about election workers and has been disbarred in New York. While once successful in taking down mobsters, his legal tactics have now become a liability, dragging him into the center of Trump’s legal battles and tarnishing his legacy.


Michael Flynn

Alias: The General
DOB: December 24, 1958
Affiliation: Former National Security Advisor, Retired Lieutenant General

Views on Democracy:
Since leaving the military, Flynn has taken an increasingly authoritarian stance on democracy. His calls for martial law to overturn the 2020 election reveal his deep disregard for the democratic process. Flynn has also aligned himself with conspiracy theories that seek to delegitimize democratic institutions, such as the baseless QAnon movement, which undermines the fabric of democratic governance. Flynn has promoted extreme actions to keep Trump in power, demonstrating a willingness to subvert democratic principles.

Why Trump Trusts Him:
Trump trusts Flynn because of his military credentials, loyalty, and willingness to take extreme, undemocratic actions to protect his presidency. Flynn’s influence over far-right groups and public advocacy for overturning election results align with Trump’s authoritarian tendencies.

Flynn’s Impact:
Flynn’s fall from grace has not diminished his influence in Trump’s inner circle. His major impacts include:

  • Undermining the Obama Administration: Flynn’s secret communications with Russian officials during the Obama-Trump transition created diplomatic tensions and demonstrated Flynn’s disregard for traditional governance.
  • 2020 Election Fraud & Martial Law: Flynn’s advocacy for martial law to overturn the election results marked an unprecedented attack on democracy.
  • QAnon Influence: Flynn’s association with the QAnon conspiracy theory has added fuel to a dangerous movement that seeks to undermine trust in democratic institutions.

Modus Operandi:
Flynn operates as a key figure in promoting far-right, anti-democratic ideologies. His calls for extreme measures, including martial law, demonstrate his willingness to abandon democratic norms entirely. Flynn uses his platform to rally support for Trump through misinformation and conspiracy theories, often aligning himself with dangerous extremist movements.

Criminal Behavior:
Flynn was convicted in 2017 for lying to the FBI about his communications with Russian officials. He later received a pardon from Trump, and since then, has remained an active proponent of Trump’s narrative that the 2020 election was stolen.


Trump and Friends Threaten Democracy

The continued presence of Bannon, Stone, Guliani, and Michael Flynn in Trump’s orbit highlights a severe threat to the integrity of American democracy. These men, convicted of crimes and guilty of undermining democratic norms, still wield significant influence within Trump’s political operation. By embracing populism, conspiracy theories, and extreme nationalism, they erode public trust in democratic institutions, pushing the country closer to authoritarianism.

Having individuals who openly disdain democracy at the helm of political movements endangers the very foundation of the American republic.

Bannon’s attempts to create chaos, Stone’s manipulation of media and politics, Flynn’s calls for martial law, and Giuliani’s relentless legal assaults all point to a future where elections and governance are dictated by force and conspiracy, not by the will of the people.

As these actors continue to shape the political landscape, it is critical to recognize the ongoing threat they pose. Democracy can only survive if it is defended against those who seek to undermine it from within through misinformation, fearmongering, and authoritarian tactics. Their influence is not just a relic of Trump’s presidency but an ongoing danger to the integrity of democratic governance.

Catch “From Russia with Lev” on MSNBC. This gripping story is about Lev Parnas, a Ukrainian-American businessman who got tangled in Trump’s political schemes, including shadow diplomacy with Ukraine and efforts to influence the 2020 election. This documentary uncovers the dark, reality-show politics that defined the Trump era through exclusive interviews and unseen footage. It premieres Friday at 9 PM on MSNBC.


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