Exclusive: Yahoo Finally Set to Strike Alibaba Share Deal — Half Now, Then Half of What's Left After Eventual IPO
Half Now, Then Half of What's Left After Eventual IPO — Yahoo is in the final stages of selling a large chunk of its stake in the Alibaba Group back to the company — in a complex deal that is set to include a multi-billion-dollar share buyback …
Context & Ripple Effects
This closes a loop that opened years ago: Yahoo's expansion of its role in China around Alibaba's 2007 IPO left the US portal holding a large stake in a company it did not control. Since early May, the two sides have been negotiating an unwind structured to manage taxes — the WSJ reported on May 5 that the deal would be taxable, which shapes why Yahoo is splitting the sale rather than exiting at once.
The timing is not incidental: Yahoo confirmed this week that Scott Thompson is out over the fake computer-science-degree affair, Ross Levinsohn is set to replace him, and the board is settling with activist Dan Loeb — so a multi-billion-dollar cash infusion lands on a new CEO's desk just as governance stabilizes.
First-order effects
- Yahoo converts part of its Alibaba holding into cash immediately, with the remainder of the sale locked behind a second tranche that only pays out after Alibaba lists — liquidity now, more later, all under a structure both sides have reportedly agreed in final stages.
- Alibaba buys back control from its largest Western shareholder before an IPO roadshow, removing the ownership overhang that has complicated its listing story since Yahoo first deepened its China position in 2007.
Second-order effects
- Because the WSJ-reported structure is taxable, Yahoo nets materially less than the headline buyback figure, pressuring whoever leads Yahoo next — Levinsohn, if confirmed — to show investors what the cash buys beyond plugging the balance sheet.
- An IPO-contingent second tranche gives Alibaba's bankers and Jack Ma a concrete incentive to accelerate the listing timetable, since the repurchase of the remaining shares only completes once public markets set a price.
Third-order effects
- The staged, IPO-linked buyback is becoming the template for Western strategic investors unwinding large Chinese internet stakes — partial exits negotiated around tax exposure rather than outright block sales.
- Each tranche Yahoo sells narrows the gap between its market value and its Alibaba holdings, sharpening the question of what Yahoo's core advertising business is actually worth on a standalone basis.
The trend: Western strategic holders of Chinese internet assets are unwinding their positions through staged, tax-structured, IPO-contingent buybacks rather than single-shot exits.