Illustration: Sarah Grillo/Axios

Carl Icahn gambled again. And won again, given Monday's news that Eldorado Resorts agreed to buy Caesar's Entertainment for $17.3 billion (including assumed debt), or $12.75 per share in cash and stock.

Why it matters: It creates the largest owner and operator of U.S. casinos, with the combined company to retain the Caesar's brand.

  • The price is a 29% premium over where shares closed Friday, and nearly an 88% increase from where they entered 2019.

Details: Icahn first disclosed a 9.8% stake in Caesar's in mid-February, and began pushing the company to sell. Caesar's quickly folded, giving Icahn three board seats and a say in picking its next CEO.

  • By the end of March, Icahn was the company's largest outside shareholder with a 15.84% stake (per S&P IQ).
  • He reportedly worked to block an $11 per share takeover offer from Eldorado which, if true, netted Icahn an additional $174 million.
  • Caesar's shares opened trading in 2019 below $7 per share, and closed Friday at $9.99 per share.

The big picture: Today's deal is the second time in less than a year that Icahn has cashed in chips at the Eldorado window, having previously sold it Tropicana Entertainment for $1.85 billion.

The state of play: Icahn also took the rare step of publicly praising the Caesar's board for "acting responsibly and decisively in negotiating and approving this transformational transaction."

  • But, true to form, he also used the moment to slam Occidental Petroleum for its proposed Anadarko acquisition, over which Icahn is suing Occidental.
"There are far too many boards that unlike Caesars, believe corporations are more like feudal systems, than democracies; that stockholders are the peasants who represent a necessary evil that must be tolerated, possibly patronized, but certainly ignored."

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