NEW YORK, NEW YORK - JUNE 03: The Gamestop company logo is seen on display at the New York Stock Exchange during afternoon trading on June 03, 2024 in New York City. Stocks closed mixed on the first day of trading in June a day that started with a technical issue that was resolved that brought trading to a stop for some of the major stocks and caused Berkshire Hathaway to be down 99.97%. (Photo by Michael M. Santiago/Getty Images)Getty ImagesGameStop’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.MORE FOR YOUGameStop’s $56 Billion Swing At eBayThe 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 $104.07. Since the $56 billion deal is 3.83 times higher than GameStop’s stock market capitalization, the financial risk for the game retailer’s shareholders is considerable.To pay for the transaction, GameStop intends to use its $9.4 billion cash pile, borrow $20 billion based on a "highly confident" debt letter from TD Securities and issue about $26 billion in fresh GME stock. GameStop sees potential backing coming from “Middle Eastern sovereign-wealth funds,” reported the Journal. The company also anticipates saving $2 billion in annual costs within 12 months — claiming the synergies would boost eBay’s earnings per share by 83% to $7.79, according to Bloomberg.eBay Says It Doesn’t Need GameStopeBay is doing well without GameStop. At the end of April, eBay reported strong first-quarter 2026 results that beat expectations. Adjusted earnings per share of $1.66 were 5% above estimates, while revenue increased 19% with help from 33% growth in first quarter advertising. For the second quarter of 2026, eBay forecast 9% revenue growth to $3 billion, reported Yahoo Finance.While concluding no shareholder action is required at this time on GameStop’s offer, eBay has reasons to think its shares can exceed $125 a share on their own. eBay’s shift towards enthusiasts and recommerce appears to be gaining momentum in 2026, driven by key acquisitions — such as Depop, TCGPlayer, and Goldin Auctions — with live commerce also contributing to a turnaround that seems to be working, according to Morningstar.eBay shares are up 137% since January 2024. “The business is firing on all cylinders,” analysts at Bernstein wrote in a report featured by The New York Times. “Why disrupt things? The turnaround is working.”Cohen plans to take his bid directly to shareholders if the board refuses. If the market believed this deal would go through or spark a bidding war, eBay’s share price would likely trade much closer to $125.Cohen’s Track Record Shows Wins — And MissesCohen’s success with pet-supplies e-tailer Chewy is a positive for him. He founded the company in 2011, sold it to PetSmart for $3.35 billion in 2017 and, in 2019, Chewy went public at an $8.7 billion valuation. Cohen’s track record at GameStop reflects mixed success. After taking a near-10% stake in September 2020, he slowed the game retailer’s decline, reduced debt and built a $9.4 billion cash pile while increasing the company’s stock market capitalization by 615% from $1.3 billion to about $9.3 billion. However, GameStop’s core retail business is still declining, and the company “never found a new business model," Wedbush analyst Michael Pachter told Fortune.Cohen’s effort to turn a roughly 11% March 2022 stake in Bed, Bath & Beyond into a successful turnaround failed. Five months later, BBBY filed for bankruptcy. BBBY’s successor sued Cohen for $47 million in alleged insider-trading profits. While a Manhattan court dismissed the parallel shareholder suit, the episode may raise questions about whether GameStop will quickly exit eBay.Cohen’s $35 Billion Compensation Target Looms Over The BidCohen has a chance to win big if he clears difficult hurdles. In January 2026, GameStop’s board granted Cohen options to purchase 171,537,327 shares at $20.66. To achieve the maximum package worth $35 billion, GameStop would need to reach a $100 billion stock market capitalization and $10 billion in cumulative earnings before interest, taxes, depreciation and amortization across nine tranches.This deal gives Cohen no salary, cash bonus or time-vesting stock. If he misses the first of the nine tranches — $20 billion in stock market capitalization and $2 billion in EBITDA — he gets nothing.GameStop says its roughly 1,600 U.S. stores could serve as authentication hubs. Wedbush remains skeptical of the value Cohen can bring to eBay. “I might be able to give you a higher than 0.001% probability that it’ll get to $100 billion," Pachter told Fortune. "But I take the underside of that bet. I’d say no, not going to happen.” What Happens NextI estimate there’s a 15% chance GameStop’s bid could succeed. For the deal to close, eBay’s board would have to capitulate or GameStop would have to win its proxy fight. After that, antitrust concerns would need to be resolved due to the overlap between eBay’s TCGPlayer and GameStop’s collectibles business. Moreover, during the months-long process, GME’s stock price would need to remain stable to unlock Cohen’s compensation package.The no-deal case seems more compelling. No rival bid has emerged. Amazon faces antitrust challenges to buying eBay; Walmart has shown no interest; and private-equity buyers would likely struggle with a $55.5 billion price tag against eBay’s existing debt. Other analysts are skeptical. Turning eBay into something worth "hundreds of billions" requires doubling its transaction commission, reversing stagnation in the number of buyers and achieving growth at a level neither Cohen nor his team has ever managed. The dilution, execution risk and absence of strategic logic for GameStop’s bid lower the likelihood of success. "Any credible offer would require substantial dilution and introduce meaningful execution risk," Bloomberg Intelligence analyst Poonam Goyal said. "When a smaller acquirer targets a much larger company, the markets tend to "question both the financing and the strategic logic," Wedbush analyst Dan Ives added.Michael Burry — who profited from the collapse of the U.S. housing market in 2008 — is a fan of GameStop. He purchased shares in the company, according to a Jan. 26 Substack post.“I believe in Ryan,” Burry wrote in the post, referring to Cohen. “I like the setup, the governance, the strategy as I see it. I am willing to hold long-term, and I am excited to see where this goes.”Burry says he recently bought more GameStop shares at $25.56.My questions: With a mere “highly confident letter” from TD Securities, can GameStop really borrow $20 billion? If so, how much strain will the borrowing put on the company’s cash flow? Will investors tolerate the dilution to their shares that will likely result from the issuance of $26 billion in fresh stock? If you believe in Burry and Cohen, these questions may not concern you and you might feel you would be missing out by not holding on to GameStop shares.However, I agree with the deal skeptics. The answers to my questions appear to be probably no, significant cash-flow strain and investors will dump GME stock for those reasons and the dilution required to finance the deal.Cohen is highly unlikely to succeed with his eBay bid.