You have to know when to hold them, and when to fold them. That's the not just slightly smug assessment by IBM executives as they reflect -- with twinkles in their eyes -- on the months-stalled Oracle acquisition of Sun Microsystems, a deal that IBM initially sought but then declined earlier this year.

Chatting over drinks at the end of day one of the Software Analyst Connect 2009 conference in Stamford, Conn., IBM Senior Vice President and IBM Software Group Executive Steve Mills told me last night he thinks the Oracle-Sun deal will go through, but it won't necessarily be worth $9.50 a share to Oracle when it does.

"He (Oracle Chairman Larry Ellison) didn't understand the hardware business. It's a very different business from software," said Mills.

Mills seemed very much at ease with IBM's late-date jilt of Sun (Sun was apparently playing hard to get in order to get more than $9.40/share from Big Blue's coffers). IBM's stock price these days is homing in on $130, quite a nice turn of events given the global economy.

Sun is trading at $8.70, a significant discount to Oracle's $9.50 bid, reflecting investor worries about the fate of the deal now under scrutiny by European regulators, Mill's views notwithstanding.

IBM Software Group Vice President of Emerging Technology Rod Smith noted the irony -- perhaps ancient Greek tragedy-caliber irony -- that a low market share open source product is holding up the biggest commercial transaction of Sun's history. "That open source stuff is tricky on who actually makes money and how much," Smith chorused.

Should Mills's prediction that Oracle successfully maintains its bid for Sun prove incorrect, it could mean bankruptcy for Sun. And that may mean many of Sun's considerable intellectual property assets would go at fire-sale prices to ... perhaps a few piecemeal bidders, including IBM.