GameStop’s surprise $55.5 billion bid for eBay — an offer more than triple its own market value — has immediately run into market skepticism, raising questions about whether the company can secure financing, win a proxy fight or avoid massive dilution as it pursues one of the most improbable takeovers in recent memory.

In premarket trading Monday, GameStop shares fell about 3.4% while eBay stock rose 7.4%.

GameStop CEO Ryan Cohen — who has a mixed record when it comes to takeovers — signed a cash-free compensation package in January. This deal would give him up to $35 billion in stock if GameStop’s market capitalization hits $100 billion and meets nine specific market-cap and cash-flow targets. That lucrative potential helps explain his logic for the deal. “EBay should be worth — and will be worth — a lot more money,” Cohen told the the Wall Street Journal. “I’m thinking about turning eBay into something worth hundreds of billions of dollars.”

Ebay stock trades at $113 a share, which is $12 below the GameStop offer of $125 a share in cash and stock. On May 4, eBay’s board confirmed receipt of the unsolicited proposal from GameStop and concluded “no action is required from eBay shareholders at this time,” according to a company release.

Cohen seems unlikely to win this deal. I envision a scenario in which eBay rejects the GameStop offer, Cohen’s proxy fight stalls, GameStop shares decline, the deal’s financing is shaky and eBay drives up its stock price through buybacks and strong growth. The result could benefit eBay shareholders while Cohen goes back to the drawing board for another way to win his $35 billion payday.

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GameStop’s $56 Billion Swing At eBay

The facts of GameStop’s proposal for eBay — Cohen began buying his now-5% stake on Feb. 4, per the Journal — make me question the likelihood of the deal’s success.

The company’s nonbinding proposal offers eBay shareholders $125 per share in a 50/50 split of cash and GameStop common stock — a 20% premium to eBay’s May 1 close of........

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