It won't happen any time soon at the current valuation. for the following reasons: First, valuation. It's just too much to swallow for Oracle for what they would get and be so dilutive that their stock value would get crushed. Second, Benioff and friends have to extract as much money in the form of stock options as possible. Now if for some reason the valuation comes down to something reasonable, like maybe $25/share, a big maybe.
It would make a lot of sense! The problem is what to pay for CRM? ORCL would ruin real earnings for years and years if they buy this money losing over-valued stock. Larry is smarter than that. If CRM grows so does ORCL as they use ORCL technology so Larry is in a win/win situation as very little is invented at CRM. After CRM tanks to fair value, then yes ORCL should buy it. What is fair value for a money losing asset? Even the most optimistic non-earnings type valuation metrics would value this stock at well less than $30/sh. We'll have to see that price before ORCL would even consider buying CRM - IMHO
I agree that CRM's price, high costs, and no GAAP earnings (or expectations for them this year or next) make it undesirable as a buy. CRM would be more desirable (comparatively speaking and not that it would even be really desirable then) if the stock price is cut in half. But then things could be more complicated if key employees leave when the stock price drops a lot because potential buyers of the company could simply hire key emplolyees and avoid any egotistical executives.