The New Al Capone
The IRS took down mobsters, now Trump wants it to serve as his.
For years, no one could take down Al Capone. He ran bootleggers, operated illegal gambling houses and brothels, extorted families and businesses, and orchestrated murders. The feds, of course, had him on their radar, but they couldn’t build a winnable case against him. Eventually, they called in the big guns: the IRS. And that’s who finally brought down America’s most notorious gangster. Forget all of the organized crime, “Scarface” was evading taxes. They’ll get you for that.
Today, President Trump is trying to remake the IRS, from an agency that takes down the Don to one that serves him.
To start, he’s commandeering the tax agency to go after his opponents. When Harvard refused to kowtow to a list of demands from the Trump administration, the president instructed the IRS to strip the university of its tax-exempt status despite no proof of wrongdoing.
It also pays to be loyal to the boss. Recently, David Eisner, a Trump-appointed Treasury official, asked the IRS to re-evaluate an audit of Mike Lindell, a “high-profile friend of the President” who served as an early and enthusiastic campaign surrogate. You scratch my back, I scratch yours.
Before you ask, no, this is not legal. After President Nixon attempted to use the IRS to access the information of 600 of his political enemies, Congress made it illegal for many Executive Branch officials—including the President—to request or interfere with an investigation of a taxpayer.
To bend the IRS to his will, the President is removing the guardrails in place, piece-by-piece. He’s driven out senior leaders—including the acting commissioner, the chief of staff, and the chief financial, privacy, and risk officers—by asking them to do things they found unethical or illegal. Then, in their place, he’s installing loyalists willing to do the dirty work. For example, he re-hired and promoted two former IRS criminal investigators who gained favor by providing whistleblower testimony to Congress alleging bias in the investigation of Hunter Biden.
The thing about organized crime is it doesn’t just affect those in the game, the whole community suffers because of it. The weaponization of the IRS isn’t just an affront to the rule of law, it prevents the agency from serving the American people.
To start, tax season is going to be a headache. In 2022, Congress boosted the IRS budget by $80 billion. Just one year later, with more staffing and more modern technology, the IRS slashed phone wait times down from 28 minutes to 3 minutes, while handling 1.3 million more calls. The IRS also launched Direct File, a free tax filing program that helped 140,803 taxpayers in its pilot year, saving them $5.6 million in tax preparation fees. But now, Elon Musk and his DOGE henchmen have set out to cut tens of thousands of employees from the IRS and shutter Direct File.
With these staff cuts, the country will also lose a lot of money to wealthy tax cheats. The Trump Treasury Department plans to fire half of the IRS’ enforcement staff. If the IRS shrinks in half, the agency would collect an estimated $395 billion fewer dollars over 10 years. Without the fear of enforcement, more taxpayers may cheat on their returns, and the lost revenue could rise up to $2.4 trillion—equivalent to how much the federal government spent on Social Security and defense combined in 2024.
It’s important to recognize what the IRS was doing that has been such an affront to this administration. The agency prioritized auditing corporate executives using their company’s private jets for personal travel and writing it off as a tax deduction. It also launched 125,000 cases focused on the richest Americans who didn’t file taxes, quickly collecting almost $500 million in taxes owed by 1,600 millionaires who hadn’t paid what they owed. It was able to match the army of lawyers the wealthiest Americans have and start enforcing the law.
And lastly, the criminal investigators—the folks that brought down Al Capone—will be weakened at best and politicized at worst. Today, long past the days of bootlegging, these investigators are protecting American communities. Last year, the IRS Criminal Investigations team co-led a Counter-Fentanyl Strike Force alongside the intelligence community and law enforcement to disrupt the illicit global drug trade. For example, they helped put sanctions in place against members of the Sinaloa Cartel, making it harder for drug traffickers to financially benefit from selling fentanyl into the United States. A couple of weeks ago, they also helped arrest a senior Sinaloa Cartel member in Arizona for drug trafficking and money laundering. Instead of providing these teams with more resources, DOGE is looking to reduce them and the administration is looking to redirect them to focus on political opponents.
The IRS is the federal agency Americans interact with most frequently. They want to be able to file their taxes in a quick, simple, and free way. What they don’t want to do is kiss the ring or do a favor first. Vice President Vance captured it best: “if the IRS can go after you because of what you think or what you believe or what you do, we’d no longer live in a free country.” In that case, we’d be under mafia rule.
What I’m Paying Attention To:
Recession Indicators? The U.S. economy officially shrank in the first quarter of 2025. The negative print was largely due to somewhat of a data quirk; companies imported way more than normal ahead of tariffs which brought down the official GDP number because of how it is measured. The scary party is that much of the effects and uncertainty of tariffs will be measured in Q2 (Liberation Day was in April), so economists are expecting things to deteriorate.
Here at WGP, we track many softer measures of a recession:
People (other than me) think Ed Sheeran is cool?1
Someone selling a FitBit for $66 on the Bloomberg Terminal (which itself costs thousands of dollars)?
What I’m Reading:
Much to Meta’s chagrin, I read Sarah Wynn-Williams memoir Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism. Honestly, I wouldn’t have known about this book or been that interested if it weren’t for Meta trying to block the book’s publication. Wynn-Williams details her journey joining/starting Facebook’s global policy team and the disinterest and disregard Facebook’s senior leadership has on their impact on the world. Nothing was overly surprising, but she paints a damning portrait of a handful of Facebook’s senior management. It’s quite well-written, but I think Wynn-Williams loses some credibility for constantly discussing why she stayed at Facebook for years despite losing her idealism without owning the fact that she was probably paid VERY well (enough to bring her nanny to Davos?!).
Watch Songwriter. He’s so talented.