this post was submitted on 01 Jun 2026
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What we need to understand about O'Leary is that:
a) He likely has an incredibly tiny penis.
and b) He is absolutely desperate to be seen in the same circle as the likes of Musk, Zuck, Gates, Bezos, etc...
The reality is that his wealth pales incomparison to those guys, at roughly 150 million. To them, he's as much a pauper as you and i are. He's a nobody. And that fucking grinds at him that he's not a part of the cool kids club. It gnaws at his insides that, in reality, the people above him AND the people below him would literally not give a shit if he fucked off back to Canada and died in obscurity.
For all of their evil, the group that O'Leary desperately wants to be seen as equal to will at least leave some sort of Legacy. They'll at least be remembered in the history books, even if just a footnote about their shitty shenanigans.
O'Leary will be forgotten as soon as he's in the ground. Probably sooner.
That's why he's suddenly forcing himself into every fucking news program, and awards shows, and trying to strike deals for massive data centers that no one wants. Because he's a sad and pathetic old man afraid of being forgotten.
also, did I mention he has an incredibly tiny penis?
You know who else has tiny/no penis? Half the population. If you want to criticize this annoying cunt, use facts.
He misrepresented himself on Canadian Sharktank for three seasons as making his money off a $3B deal with Mattel. It was only in season 4 he was outed as having no equity in that deal. The deal eventually made Mattel -$3B.
He started the O'Leary fund off his Sharktank brand. It under performed every year and eventually got sold at a loss. Everyone lost. Every call he made was a loser.
In 2019, O'Leary and his wife were speeding on a boat across a lake at night, when they hit another boat and killed two people. Unclear who was driving the boat, police did not check sobriety. O'Leary settled in a secret settlement. O'Leary and wife got off in criminal court. After killing two people, O'Leary sued the victims for $3M but the case was not won.
Thankfully, this piece of shit moved to Boston.
His penis has nothing to do with it. Stop obsessing over peoples genitals.
Just raccoons.
But if we don't obess over penises then how will people know how masculine we are compared to the people we don't like!!!!1!1!1!1!!1!!1one!1!
Lighten up.