The Warning
How the Loop Came into Being and How it Broke Democracy
The founders didn’t trust one another.
They certainly didn’t trust us.
They were afraid of faction, tyranny, and corruption.
They warned us.
They were right.
In the Federalist Papers Alexander Hamilton, James Madison, and John Jay left a trail of breadcrumbs to help us understand the thinking behind the constitutional form of government they pioneered here in America. Madison warned in Federalist 10: “Measures are too often decided, not according to the rules of justice, and the rights of the minor party; but by the superior force of an interested and overbearing majority.”
They wanted people in their time and in ours to understand the intention behind the design of the system. They didn’t want some future generation to rely purely on the literal words included in the constitution in order to interpret it. They wrote thousands of words across hundreds of pages to explain the nuance behind the ingenious system of constitutional checks and balances intended to prevent overreach, malfeasance, and corruption.
Somewhere the engine seized and the checks and balances of the system stopped working. Congress is ineffectual, executive power is unchecked, and the neutrality of the judiciary has been compromised.
Madison warned in Federalist 47: “The accumulation of all powers, legislative, executive, and judiciary, in the same hands, whether of one, a few, or many, and whether hereditary, self-appointed, or elective, may justly be pronounced the very definition of tyranny.”
They understood human nature and the corrupting influence of power. They anticipated the malignancy associated with money.
We stopped listening.
Looking at our Past
It wasn’t always this way. Throughout our history leaders like Sam Houston, Howard Baker, and John McCain have put country ahead of party, ahead of personal ambition, or political advantage.
Sam Houston voted against secession in 1861 and destroyed his political life, dying during the Civil War, a pariah in Texas whose independence he once championed.
Earl Warren, an Eisenhower appointee and former Republican governor stood up for injustice and was not married to ideology or a strict interpretation of the constitution when he helped shepherd a unanimous decision in Brown vs. Board of Education in 1954.
Howard Baker stood up to a president of his own party and conducted hearings that ultimately led to numerous convictions and the resignation of President Nixon.
Not surprisingly Senator John McCain, the former Prisoner of War continued to fight into the last months of his life.
In July 2017, in a final act of defiance and political courage in a life marked by courage, dying of brain cancer, Senator McCain walked onto the Senate floor and voted against his party to stop ACA repeal. Not because he loved Obamacare. Because the process was corrupt—no hearings, no regular order, no bipartisan input.
One dying senator, freed from caring about his political future, showed what governance looks like when The Loop doesn’t control it.
The Loop
Over the last few weeks I wrote about the drug war and how the government has become hostage to the contractors who profit from its failure. I could just as easily have written about healthcare, Afghanistan, Iraq, or the paralysis on entitlement reform. The Loop infects everything—because the money flowing through it has captured all three branches of government.
Peter Senge calls these institutional failures “learning disabilities”— pervasive systemic blindness that prevents organizations from recognizing their own role in perpetuating failure. When the system itself is designed to reward failure with more appropriations, learning becomes impossible.
When we look at the Loop we see the manifestation of the warnings that Hamilton, Madison and Jay wrote about in the Federalist papers. The executive, legislative, and judicial branches have all been infected by the vast sums of money flowing both into and out of the political system.
What are the reinforcing mechanisms of the loop?
Gerrymandering -> Incumbency
Gerrymandering creates safe districts by drawing legislative boundaries to ensure a substantial majority of voters from one party reside within the district, effectively insulating the incumbent from serious challenge and driving incumbency. By packing opposition voters into a few districts or by spreading them thinly across many districts so they cannot form a majority, the partisan mapmakers virtually guarantee the victory of their party’s candidate. This assurance of victory leads to incumbents facing little to no competitive general election challenge, allowing them to focus on pleasing their party’s base—often leading to more partisan and less moderate governance—without fear of being unseated.
This system is acutely reflected in the declining number of genuinely competitive congressional districts. For the 2024 election cycle, for instance, only around 27 out of the 435 U.S. House districts were rated as “Toss-ups” by the Cook Political Report, meaning over 93% of the seats were considered solid or leaning for one party. This continues a trend, as only 39 districts (8.5%) were tracked as battleground races by Ballotpedia in the 2022 elections, and even in the 2020 election, a key analyst rated only 27 districts as “Toss-ups.” Ultimately, this severely limits voter choice and makes it extremely difficult for any challenger to defeat the entrenched incumbent, thus artificially boosting the rate of re-election.
Duopoly of the two major political parties -> Stifles New Voices
The entrenched duopoly of the Democratic and Republican parties often stifles genuine democratic representation by limiting voter choice and fostering intense polarization. The winner-take-all electoral system, restrictive ballot access laws, and media focus on only the two major parties create formidable barriers for third-party and independent candidates, effectively ensuring that a wide spectrum of public interests remains unrepresented in government. In Florida, for example, independent candidates must collect nearly 145,000 signatures to appear on the ballot for statewide office, while major party candidates need only file paperwork and pay a small fee. This dynamic compels voters to choose the “lesser of two evils,” reduces accountability, and incentivizes gridlock and partisan rivalry over bipartisan problem-solving for the average citizen.
Partisan selection of federal judges including justices of the supreme court -> Citizens United
The role of partisan loyalty in the judicial selection process is widely considered a foundational factor that led to the Citizens United v. FEC decision. Presidents appoint judges and justices who are expected to interpret the Constitution according to a certain political ideology, leading to a bench often divided along predictable ideological lines. The conservative Federalist Society, led by Leonard Leo who raised over $250 million for judicial campaigns, vetted the justices who formed the Citizens United majority—part of a decades-long strategy to capture the federal judiciary. This partisan composition determines which cases the court will hear and produced the narrow 5-4 majority in Citizens United, which elevated corporate and union campaign spending to a form of protected free speech—reflecting the judicial philosophy of the conservative political movement that put those justices on the bench.
Unlimited and unrestricted money flowing to political candidates -> Overseers funded by the Overseen
The unlimited spending from Citizens United didn’t just add money to politics; it inverted the accountability structure of our democracy. The officials responsible for writing and enforcing regulations are now heavily financed by the very industries they are meant to oversee. This constant influx of dark money creates an environment where the government’s overseers are either indebted to or fearful of their corporate-backed patrons. The predictable consequence is lax enforcement and legislation that systematically prioritizes donor wealth over public welfare.
Revolving door between Washington and Industry -> The regulators move from government to the industries they formerly regulated
The “revolving door” is a phenomenon where former government officials who were once responsible for overseeing specific industries quickly take up lucrative positions as executives or lobbyists for those very same companies, essentially being funded by the overseen. A Project on Government Oversight study found that in the defense sector alone, over 380 high-ranking Pentagon officials and military officers took jobs with defense contractors within two years of leaving government service between 2008 and 2018.
Scott Gottlieb, a former FDA Commissioner (2017–2019), joined the board of directors at pharmaceutical giant Pfizer soon after leaving his government post. He also had previous ties to the pharmaceutical industry before his government service, illustrating the circular nature of the door.
Heidi Grant, the former director of the Defense Security Cooperation Agency (DSCA), was hired by defense contractor Boeing—a move that was scrutinized as she had publicly advocated for the firm’s fighter jets while still in government.
No Branch is Immune
No institution is immune to the effects of money. ProPublica documented that Justice Clarence Thomas received hundreds of thousands of dollars in undisclosed gifts from conservative benefactor Harlan Crow, including luxury travel valued at over $500,000 for a single trip and over $150,000 in private school tuition for a relative Thomas was raising. Justice Samuel Alito accepted a private jet flight from billionaire Paul Singer worth over $100,000 to a luxury fishing lodge charging $1,000 per day. Singer’s hedge fund later had cases before the Supreme Court. Alito never recused himself.
Campaign finance laws were strengthened in the aftermath of Watergate and then again with the Bipartisan Campaign Finance Reform act of 2002 also known as the McCain Feingold Act. Senator John McCain Republican of Arizona and Senator Russ Feingold Democrat of Wisconsin understood the risks posed by The Loop and championed campaign finance reform. McCain-Feingold banned unlimited soft money contributions to political parties and restricted corporate election spending.
Then came Citizens United—a 2010 Supreme Court decision that overturned McCain-Feingold’s restrictions, ruling that corporate spending is protected speech under the First Amendment. Campaign spending more than doubled after Citizens United, jumping from $7.1 billion in 2008 to $16.4 billion by 2020. Super PACs alone have spent $6.4 billion on federal elections since 2010. This ruling turned the spigots on for unlimited dark money to flow into the political system.
I wrote a few weeks ago that democracy is like an egg, hold it gently — it’s fragile and can break. Right now our eggs are a little scrambled. It’s up to us to follow the breadcrumbs that our founders left us to restore balance and order.