It’s been about six years since Microsoft Corporation (NASDAQ:MSFT) offered to buy Yahoo! Inc. (NASDAQ:YHOO) for $31 per share. So should the company try again? Forbes contributor Peter Cohan considers the possibility with one reason in mind. Maybe Microsoft would like Yahoo! CEO Marissa Mayer to replace Steve Ballmer. (But then again, if Microsoft really wanted Mayer, would it really have to buy Yahoo to get her?)

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Microsoft could offer 30% premium

According to Cohan, Microsoft could offer $52 per share for Yahoo, which would be a 30% premium. He suggests that this may be the only way the company will be able to snag a CEO who can boost its share price even though it is losing market share.

He notes that under Mayer’s leadership, Yahoo! Inc. (NASDAQ:YHOO) has seen falling revenues in its core business. Statistics from eMarketer indicate that the company’s share of the digital ad market declined from 6.8% to 5.8% in 2013.

Topeka Capital analyst Victor Anthony estimates that Yahoo has a whole is worth $50 to $52 a share, but that its core business alone is worth only $10 a share. He estimates that Yahoo’s 24% stake in Alibaba is worth $30 a share, while Yahoo Japan is worth $7 per share. Cohan says these assets have been a part of Yahoo for years, but the only thing that has changed is the fact that Mayer is now at the helm. He said if these valuations of Yahoo’s parts are truly accurate, then they should have been reflected in Yahoo’s share price before she took over the company.

Where Microsoft’s purchase of Yahoo might work

Cohan examines the four tests of whether an acquisition would work and believes that it could work in two of the four—maybe. He said it could work because Microsoft Corporation (NASDAQ:MSFT) would be acquiring a company which participates in an attractive industry. In spite of its falling market share, Yahoo! Inc. (NASDAQ:YHOO)’s digital display business is big and even growing. However, he notes that the digital ad market is less attractive than, say, mobile advertising.

The other place where the deal might possibly pass is integration. He believes Mayer’s management style could fit in well at Microsoft, which had been using the “stack ranking approach” up until recently. (But then again, why would Microsoft want to go backwards? This would be a mistake, in my view).

Where a Microsoft – Yahoo deal probably wouldn’t work

He says the deal definitely fails the other two tests. After the acquisition, both companies are supposed to be able to more effectively compete. However, this doesn’t appear to be the case with a deal between Yahoo and Microsoft, as both companies’ share of the digital advertising market is expected to continue falling.

The other place where he sees failure is in the price Microsoft Corporation (NASDAQ:MSFT) might have to pay to buy Yahoo. He said it should be less than the present value of the company’s future cash flows. However, he notes that shares of Yahoo have shot up 150% since Mayer came to the company, so he sees them as being inflated. It would seem difficult, if not impossible, for Microsoft to get back the 30% premium it might pay on Yahoo shares.