Carl Icahn is reportedly making a last-minute push to derail Tilman Fertitta’s take-private of Caesars Entertainment, but industry observers are skeptical the corporate raider can overcome the board’s clear preference for the Houston billionaire’s $31-per-share offer.

According to Bloomberg, Icahn has engaged investment bank Jeffries Financial to explore a $5 billion debt financing package underpinning a competing $33-per-share proposal. The move comes as Caesars’ go-shop window closes on 11 July, leaving little time for serious deliberation. Fertitta’s all-cash deal, valued at $17.6 billion including assumed debt, already has board backing and firm financing commitments. Time, frankly, is running out.

The Refinancing Question

Icahn’s bid is structured as a liability management exercise, a controversial financing mechanism that restructures debt rather than providing traditional equity. These arrangements have gained prominence as interest rates have remained elevated, but they carry notable risks. As CNBC’s David Faber observed on Wednesday, the debt package is essentially tied to current management. Should key executives depart, refinancing obligations could multiply dramatically. That makes execution substantially more difficult and the deal far less attractive to lenders.

The regulatory pathway also favours Fertitta. He’s already begun the suitability process with Nevada regulators, who will likely coordinate with federal antitrust authorities. Admittedly, Fertitta’s ownership of Golden Nugget Casinos creates direct competitive overlaps in Nevada and other jurisdictions. But the regulatory framework for such combinations is established from the Eldorado-Caesars merger in 2020. An Icahn deal would face similar scrutiny with a less certain outcome given the alternative proposal still under active consideration.

History and Timing Work Against Icahn

Icahn’s prior involvement with Caesars complicates his positioning. He orchestrated Eldorado’s acquisition of Caesars five years ago, a deal that proved disastrous for public shareholders. The stock is down nearly 70 percent since then, suggesting limited appetite for a second Icahn-led restructuring among investors and board members alike.

That said, Icahn’s board representation through recent Caesars Enterprises appointments gives him a seat at the table. A diminished one, mind you. The departure of board member Courtney Mather, a former Icahn Enterprises managing director, effective 6 July, further weakens his informal influence as the window closes.

For Caesars shareholders, the timeline itself may be decisive. Fertitta’s deal offers certainty and immediate momentum. Icahn’s proposal requires last-minute debt packaging and carries greater execution risk. Unless the board perceives a material difference in deal protection, the path of least resistance runs squarely through Fertitta’s existing proposal.

What the team thinks

Sheena McAllister says:

While the financial mechanics of Icahn’s counter-offer are undoubtedly compelling, what’s missing from this analysis is the regulatory dimension that could prove equally decisive: the UKGC’s position on change of control and the timeline for license reassessment under either bidder. Fertitta’s established relationships with UK regulators and proven compliance track record may give him a strategic advantage that Icahn’s higher offer simply cannot offset, particularly if the go-shop window forces accelerated due diligence on regulatory approvals. From a governance perspective, the board’s preference likely reflects not just financial terms but confidence in execution certainty, where regulatory headwinds could transform paper value into costly delays.