Trump's $48M Mystery Loan: Judge Flags Potential Tax Evasion in Latest Filing

Former President Donald Trump is facing fresh scrutiny over a suspicious $48 million “loan” that may never have existed. Former Judge Barbara Jones, now serving as special monitor in the case, sent a bombshell letter to Manhattan Supreme Court Justice Arthur Engoron on Friday, highlighting serious irregularities in Trump Organization’s financial records.

The Red Flags

The centerpiece of Jones’s concerns: a purported $48 million loan to Chicago Unit Acquisition LLC, a Trump-owned entity that appears to be defunct or non-operational. Here’s why this matters:

• The inconsistency: Trump’s recent financial disclosures (as of October) show a debt exceeding $50 million to the same company—contradicting Trump Organization lawyer Alan Garten’s claim that it was merely an “internal loan.”
• The timing: This mirrors a 2016 strategy Trump disclosed to The New York Times, where he deliberately kept outstanding debt rather than settling it—a tactic Mother Jones reported in 2019 as a possible method to avoid income taxes on forgiven debt.
• The expert take: Tax attorney Martin Lobel told outlets the pattern “could signify tax evasion.” Georgetown law professor Adam Levitin has previously called such strategies “pretty brazen.”

What’s at Stake

These inconsistencies undermine Trump’s financial disclosures to government bodies like the Office of Government Ethics (OGE) and raise questions about the Trump Organization’s official financial statements.

Garten pushed back, claiming the monitor’s letter contains “inaccuracies” and pledged to address the issues in court. But the numbers don’t add up—at least not yet.