Election Night. No Plan. $48.9 Million.

I. The Morning After

November 6, 2024. Donald Trump wins the presidency. The Pillar Two global minimum tax — the OECD framework that would close the tax haven loopholes used by the world's largest corporations — becomes, as a practical matter, finished. A Trump administration will not enforce it. Everyone with skin in the game knows this the moment the networks call Pennsylvania.

November 7, 2024. The first trading day after Election Night. The markets open. And Stephen J. Squeri, Chairman and Chief Executive Officer of American Express, exercises every outstanding stock option he holds.

Not some of them. All of them.

Options that had been sitting unexercised for three years — granted in 2021 and 2022, exercisable since then, carrying expiration dates in 2028 and 2029, with four and five years of remaining life — are exercised in their entirety on the morning of November 7, 2024. All 170,632 shares. Sold immediately. At prices ranging from $284.90 to $288.54. Gross proceeds: $48,894,858.

There is no Rule 10b5-1 trading plan protecting this transaction. Not a word about one in any footnote. The SEC Form 4 confirms it in a single field.

aff10b5One = 0. That is the SEC's field for affirming that a transaction was made under a pre-established, arms-length Rule 10b5-1 trading plan — the safe harbor that insulates corporate insiders from insider trading liability when they sell on a fixed schedule established before material non-public information exists. The field is zero. There is no plan. There is no schedule. There is no affirmative defense.

What there is: a Chairman and CEO who watched the election returns, waited for the market to open, and exercised three years of accumulated stock options in a single morning.

II. The Options He Didn't Need to Exercise

This requires a moment of attention, because the timing is only remarkable if you understand the alternative. Squeri did not exercise these options because he had to. He had years.

Batch 1 had been exercisable since January 2021 — nearly four years. Batch 2 since January 2022 — nearly three years. Neither was anywhere near expiry. On the morning of November 7, 2024, both batches had four to five years of remaining life.

He exercised both. Immediately. Sold all 170,632 shares across five tranches before the day was out, capturing prices between $284.90 and $288.54 per share — near the post-election market rally peak for AXP. Net gain after exercise costs: approximately $31.86 million in a single trading session.

III. What American Express Had at Stake

The timing of Squeri's exercise is not interesting in isolation. It is interesting because of what American Express stood to gain from the political outcome he was apparently trading on.

American Express routes profits through subsidiaries in Jersey — the Channel Island jurisdiction that is not subject to the United Kingdom's standard corporate tax regime. The OECD's Pillar Two framework — the global minimum tax of 15% that 140 countries had agreed to implement — would have eliminated the advantage that structure provides. Jersey announced it would implement Pillar Two for fiscal years beginning January 1, 2025.

A Trump victory made Pillar Two withdrawal near-certain. The United States is not legally bound by OECD agreements, and Trump had made clear throughout the campaign that he viewed international tax coordination as an infringement on American corporate interests. American Express's Jersey structure saves the company an estimated $423 million annually under the Pillar Two framework. View Dashboard →

On January 20, 2025 — seventy-four days after Squeri's November 7 exercise — President Trump signed an executive order declaring that the OECD's Global Tax Deal has "no force or effect in the United States." The American Express Jersey structure was protected. The $423 million annual advantage was preserved.

IV. The Political Record

The natural question is whether Squeri had a pre-existing relationship with the Trump orbit that might explain advance knowledge beyond what every market participant could observe on election night. The Federal Election Commission record answers that question.

Stephen Squeri has never donated to Donald Trump. Not once. Not at any level.

No contribution to the Trump campaign in 2020 or 2024. No contribution to Save America PAC. No contribution to the Trump Vance Inaugural Committee. No contribution to any Republican leadership PAC. No contribution to the NRCC.

His confirmed political giving from Westfield, NJ — his home address on record — runs as follows:

The Sinema pattern deserves a paragraph of its own. In August 2022, Senator Sinema was the deciding vote in negotiations over the Inflation Reduction Act. She ultimately secured the removal of the carried interest loophole closure and the corporate minimum tax provisions — provisions that would have targeted exactly the kind of offshore tax structures that American Express uses in Jersey. Squeri donated $8,700 to Sinema in September 2022, one month after her decisive vote. He donated another $7,100 in May 2023, after she left the Democratic Party for Independent status. Total: $15,800 to the Senator who protected his company's tax structure under a Democratic administration.

The pattern is consistent: Squeri pays the gatekeepers of tax legislation — Democratic Senate leadership (Schumer), the pivotal Democratic tax vote (Sinema) — and maintains a local Republican relationship (Lawler). He has never paid the executive branch. He has never paid Trump.

Which is precisely what makes the November 7 trade so stark. He had no access relationship with the incoming administration. He had no reason to know anything the rest of the market did not know. On election night, Trump won. The next morning, Squeri exercised everything. No plan. No schedule. No protection.

"The options had four years left. He exercised them on the first morning the policy answer was known."

V. What the Law Requires — and What It Doesn't Cover

Squeri is a corporate executive, not a member of Congress. The STOCK Act — the law that prohibits members of Congress and executive branch officials from trading on material non-public information — does not apply to him. He is subject to standard securities law: Section 10(b) of the Securities Exchange Act and SEC Rule 10b-5.

Those provisions prohibit trading on material non-public information. The question this dispatch cannot answer — and that only investigators with subpoena power could answer — is whether Squeri possessed material non-public information on November 7, 2024, beyond what every market participant knew from watching election returns. Cases →

What this dispatch can document:

VI. The Broader Cluster — Abbott, Thermo Fisher, the Revolving Door

Squeri's November 7 trade is the sharpest single data point in a broader pattern this series is documenting across ten companies, two accounting firms, and one Treasury official who moved directly from lobbying for the largest Pillar Two beneficiary to negotiating the OECD exemption that protects it.

The cluster includes:

• Abbott Laboratories — shifted a subsidiary from Bermuda to Malta on December 19, 2024 (zero employees, $17 billion in reported income, zero taxes paid), then donated $500,000 to the Trump inaugural fund on December 24, 2024 — five days after the Malta move and 27 days before Trump's Pillar Two EO. Three active IRS Tax Court dockets. View Suspects →
• Thermo Fisher Scientific — $3.5 billion in Malta tax savings, the largest single Pillar Two benefit in the dataset. CEO Marc Casper sold $42.9 million in TMO stock across six transactions from June through December 2024 under two overlapping 10b5-1 plans — one adopted while the other was still executing.
• Rebecca Burch — Managing Director, EY Washington Council. Registered lobbyist. Q1 2024: filed as lobbyist for Thermo Fisher Scientific on GILTI and FDII — the tax provisions that enable Malta IP routing. April 2025: appointed Treasury Deputy Assistant Secretary for International Tax Affairs, becoming the top U.S. delegate to the OECD. January 5, 2026: Treasury announces OECD Side-by-Side exemption, permanently shielding U.S. companies from foreign Pillar Two top-up taxes. The loop is complete: EY designs the structures, EY lobbies for the beneficiary, EY's official moves to Treasury, and the exemption is secured.

Parts Two and Three of this series will document the Abbott three-event cluster and the Burch revolving door in full. What this Part One establishes is the cleanest single transaction in the dataset: one CEO, one election night, one decision, zero plan, $31.9 million net.