Here's the part that makes this more than just a bad attempt at humor: this comes on the heels of multiple fatal shootings involving federal immigration agents, increased enforcement that ignores people's civil rights, and other acts of violence. People are dead. Families are grieving. And a billionaire CEO thought it was a good idea to riff on deportation for laughs.
Read the room.
As management-side counsel, I spend a lot of time telling executives that words matter. Culture isn't what's printed on the lobby wall. It's what leaders say and do when the spotlight is on them. When you talk about "trust" and "equality" in one breath and joke about immigration raids in the next, don't be surprised when your employees call foul.
This isn't about politics. It's about judgment. Poor judgment.
When a general manager publicly says the jokes were "indefensible" and don't align with his values, that’s not a minor PR hiccup. That's your own leadership team distancing itself from you. When employees start circulating letters demanding policy changes and public denunciations, you've turned a keynote into a crisis.
Could this have been avoided? Of course. "Just do the corporate presentation." Talk about products. Talk about growth. Talk about strategy. Do not make deportation the punchline. Don't make your international employees the butt of a tasteless joke.
Humor in the workplace is tricky. Humor about immigration enforcement—especially amid real-world violence—is radioactive. Leaders who don't understand that are either insulated from reality or indifferent to it. Neither is a good look.
If you're the CEO, you don't get to test-drive edgy material at the expense of your workforce's sense of safety and decency. If you make vile jokes about ICE raids, don't act shocked when your employees decide you're the problem, or when you're nominated as the Worst Employer of 2026.