Every year, Santa and I get together at his place, break out the nog, boogey down to some righteous classic rock and talk about corporate America’s naughtiest CEOs.

Sure they make a lot of dough but the fat man can’t resist filling their Christmas stockings with big black lumps of coal. And I don’t blame him one bit.

While Santa insists on keeping our methodology strictly on the down low, I can say we focus solely on chief executives of publicly-traded American companies. Even with that narrow scope, it always amazes me how many CEOs are naughty year after year.

Without further ado, here’s our Worst CEOs of 2019 list, counting down from …

No. 5: Jack Dorsey, CEO, Twitter

I’d call Twitter today’s Yahoo except Yahoo had a heyday. Not Twitter. In the five years since taking over as halftime CEO, the stock has gone nowhere. Literally. And not accepting political ads is a remarkably dumb decision. If nothing else, Twitter is a cesspool of vitriolic political banter. That’s okay. Taking money for legitimate ads, not okay. That makes no sense. Don’t even get me started on Dorsey’s bizarre life hacks. I think the guy’s certifiable, but that’s just me.  

No. 4: Dara Khosrowshahi, CEO, Uber

Five years ago Uber was valued at $50 billion. Two years later it ousted founding CEO Travis Kalanick for being too combative and competitive for the great awokening. The company was valued at $68 billion. It hired Khosrowshahi and his silver spoon, brought in a team of diversity and inclusion consultants, and dismantled Uber’s hard-charging culture. That was all a big mistake. Today the company is worth, wait for it, $50 billion.    

No. 3: Dennis Mullenberg, former CEO, Boeing

I don’t think anyone has a clear picture of the Boeing 737 Max situation, and that’s a real problem. By now Boeing should. We all should. And we don’t. We don’t know what caused two jetliners to crash or if the problem has actually been solved or not. This has morphed from PR disaster to leadership crisis, and that means Mullenberg had to go. Boeing’s board is an odd group, but I do think the directors made the right call.

No. 2: Bernardo Hees, CEO, Kraft Heinz

Private equity firm 3G Capital’s strategy of buying consumer brands and cutting costs to drive growth seemed to make sense … until it didn’t. As CEO of Kraft Heinz, 3G partner Hees let a disastrous 2018 bleed into 2019, announcing a $15.4 write-down of Oscar Mayer and Kraft brands, a $12.6 billion loss and an SEC investigation. He also slashed dividends in the wake of changing consumer tastes the now-gutted company was in no position to address. KHC lost a third of its value and gave Hees the heave-ho.  

No. 1: Heather Bresch, CEO, Mylan

When Mylan and Upjohn merge in 2020 Bresch will step down, putting an end to an eight-year reign that included a tax inversion move to the Netherlands, driving legislation to create an effective EpiPen monopoly, then jacking up prices and gouging customers. Bresch made a fortune while Mylan’s stock lost three quarters of its value over the past 5 years. The shrewd executive certainly knew how to play the system.  

Until next year …

Image credit Jack Dorsey @jack / Twitter