Never-before-seen IRS records show that CEOs are sometimes making multimillion-dollar bets on the stocks of direct competitors and partners — and doing so with exquisite timing.

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The Big Story
Thu. Mar 16, 2023

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Wealthy Executives Make Millions Trading Competitors’ Stock With Remarkable Timing <[link removed]> Never-before-seen IRS records show that CEOs are sometimes making multimillion-dollar bets on the stocks of direct competitors and partners — and doing so with exquisite timing. by Robert Faturechi and Ellis Simani

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The Secret IRS Files

The Secret IRS Files: Trove of Never-Before-Seen Records Reveal How the Wealthiest Avoid Income Tax <[link removed]> ProPublica has obtained a vast cache of IRS information showing how billionaires like Jeff Bezos, Elon Musk and Warren Buffett pay little in income tax compared to their massive wealth — sometimes, even nothing. by Jesse Eisinger, Jeff Ernsthausen and Paul Kiel <[link removed]>

The Billionaire Playbook: How Sports Owners Use Their Teams to Avoid Millions in Taxes <[link removed]> Owners like Steve Ballmer can take the kinds of deductions on team assets — everything from media deals to player contracts — that industrialists take on factory equipment. That helps them pay lower tax rates than players and even stadium workers. by Robert Faturechi, Justin Elliott and Ellis Simani <[link removed]>

Lord of the Roths: How Tech Mogul Peter Thiel Turned a Retirement Account for the Middle Class Into a $5 Billion Tax-Free Piggy Bank <[link removed]> Roth IRAs were intended to help average working Americans save, but IRS records show Thiel and other ultrawealthy investors have used them to amass vast untaxed fortunes. by Justin Elliott, Patricia Callahan and James Bandler <[link removed]>

Ten Ways Billionaires Avoid Taxes on an Epic Scale <[link removed]> After a year of reporting on the tax machinations of the ultrawealthy, ProPublica spotlights the top tax-avoidance techniques that provide massive benefits to billionaires. by Paul Kiel <[link removed]>

How the Wealthy Save Billions in Taxes by Skirting a Century-Old Law <[link removed]> Congress outlawed tax deductions on “wash sales” in 1921, but Goldman Sachs and others have helped billionaires like Steve Ballmer see huge tax savings by selling stocks for a loss and then replacing them with nearly identical investments. by Paul Kiel and Jeff Ernsthausen <[link removed]>

The Great Inheritors: How Three Families Shielded Their Fortunes From Taxes for Generations <[link removed]> In the early 1900s some of the wealthiest Americans claimed their fortunes would never last through the generations. A century of tax avoidance later, the dynasties are going strong. by Patricia Callahan, James Bandler, Justin Elliott, Doris Burke and Jeff Ernsthausen <[link removed]>

When You’re a Billionaire, Your Hobbies Can Slash Your Tax Bill <[link removed]> Thoroughbred horses, auto racing, massive ranches, luxury hotels. The hobbies and side businesses of the ultrawealthy create huge write-offs that can let them get away with paying little or no income tax for as much as a decade at a time. by Paul Kiel, Jesse Eisinger and Jeff Ernsthausen <[link removed]>

America’s Top 15 Earners and What They Reveal About the U.S. Tax System <[link removed]> An unprecedented trove of leaked IRS data shows who reported the most income in America from 2013 to 2018, as well as their tax rates, revealing that the very richest pay lower rates than the merely rich. by ProPublica <[link removed]>

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