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Why did the U.S. Capitol insurrection on January 6th, 2021 occur given the United States has spent over two decades investing in homeland security efforts to prevent such attacks? I argue the critical juncture of the September 11th, 2001 terrorist attacks, and subsequent creation and institutionalization of homeland security afterwards, provided a new reservoir of power that aggrandized the presidency, thus facilitating future abuses. Utilizing the findings from the House Select Committees’ Jan 6th Report and court documents from convicted insurrectionists, I identify ways in which Washington D.C., as a federal enclave, acts as a sort of constitutional “blackhole,” where the checks and balances envisioned by the Framers cannot function as intended. Madison’s concept of a “double security,” where the national and state governments check each other as articulated in Federalist 51, can no longer function given subsequent constitutional developments. Findings from the legislative branch show that former President Trump took steps to overturn the results of the 2020 presidential election, and the subsequent response by subordinates to counter his constitutional violations resulted in additional violations by those serving at the president’s pleasure. This research has important implications for American democracy. Presidency scholars have previously argued for more power to flow to the executive branch. However, the riot at the U.S. Capitol shows that enabling the executive branch is not without grave risks that threaten the republic.