One of the more unusual situations in the current stand-off between Yahoo and Microsoft is the stress it has likely put on the longtime professional relationship and personal friendship between Yahoo President Sue Decker (pictured here) and Blackstone Group’s Jill Greenthal.

That’s because Greenthal (pictured here) is advising Microsoft on this deal, along with Chuck Cory and Paul Taubman of Morgan Stanley (who was actually Time Warner’s banker in its disastrous AOL deal).

Yahoo is being repped by Goldman Sachs, Lehman Brothers and Moelis & Company, an advisory boutique. All the firms on both sides stand to reap hundreds of millions in fees, if the deal is consummated.

Greenthal is a good pick for Microsoft to get the job done. She has a long-time knowledge of Yahoo, having worked with the company when she was at the Credit Suisse Group on the $1.45 billion purchase of Overture, one of Yahoo’s smarter purchases.

And her ties to Decker go back even further, when Greenthal was a banker at Donaldson, Lufkin & Jenrette. The pair worked together frequently at DLJ, where Decker was an analyst and research director before heading to Yahoo.

Back in 2003, in a BusinessWeek profile of Decker, Greenthal noted about Decker’s tenure at DLJ: “[Executives] didn’t always like her opinions of their company or industry, but they respected her.”

A source in Silicon Valley who knows both Decker and Greenthal said that the two have avoided speaking since the unsolicited Microsoft bid was launched by Microsoft CEO Steve Ballmer in an evening phone call to Yahoo CEO and Co-Founder Jerry Yang two weeks ago.

But one might also imagine their bond could also become a critical bridge in bringing the companies to finally make a deal, as many big shareholders are urging and Yahoo has been resisting.

That debate has been all over the Web since News Corp. won its battle to buy Dow Jones (owner of this site) last week, including posts by Jeff Jarvis and Fred Wilson in favor of the move.

But former MarketWatch head Larry Kramer disagreed, noting that his old site should be the free product, while the Journal’s content should remain premium.

Sorry, Larry, but I vote–and I know Murdoch (pictured here from a magazine spread with an Apple computer at the ready, apparently) definitely does not preside over a democracy–yes, ma’am, um, sir, for a free WSJ.com.

(And just to show this is not a kiss-up to the new boss, but a cogent analysis of the landscape for the Journal moving forward under Murdoch, here is a video interview posted below that I did in Los Angeles with Beet.TV’s Andy Plesser back in May about the possible News Corp. takeover and how I felt about the situation. Not so happy and also really wrong about Rupe’s chances of winning Dow Jones, as you will see.)

Also, I have posted many times on this subject, such as this recent piece.

There are, of course, valid arguments to be made to keep the Journal’s much-admired online subscription model, combined with freeing up more content offerings over time.

Interestingly, in an interview with paidContent.org last week, WSJ publisher Gordon Crovitz said: “So far, our analysis says the way to maximize revenues and earnings is to have a mixed model.”

While I hate to differ with Crovitz, who helped us immeasurably in getting this site up and running as a free one, I think an open and ad-supported model is the only way to go now, especially under a larger and more powerful (and, most important, global) company like News Corp. that can really vault the site to higher prominence and higher traffic.

And given that the Journal’s online site garners estimated revenues of about $65 million from its paid efforts, which is admirable, it is chump change for News Corp. to try turbocharging the site as a free one, an experiment that will surely pay back the short-term cost.

An interesting analysis released last week by Lehman Brothers’ Doug Anmuth looks at the trade-off–more page views are likely to be gained by going free, although with possibly lowered ad revenues in the short term and lower ad revenues per page in general.

That sounds about right, as it is likely in time and with the marketing muscle of News Corp. that WSJ.com could go from its current 2.6 million unique visitors globally a month to three times that or more.

More importantly, while it has almost hit an impressive 1 million paid subscribers, an audience that has been growing, the online paid site is only going to gain so many more subscribers before that paid-wall people hit finally takes a hit itself.

Most importantly, while a good product, the paid version simply creates a situation in which the Journal is not as relevant as it could and should be. I know Journal execs have heard this before and would argue the paper is influential with a much more elite audience willing to pay the annual fee for access.

But, to my mind, too much of that is a lot of expense-account money talking. That same audience would remain and expand in an unpaid scenario and also add many more who get less excellent, but still adequate, coverage from a plethora of finance sites now.

(By the way, the rumors that the New York Times will end its TimesSelect, which gates the best stuff behind a paid wall, are back again, courtesy of the Murdoch-owned New York Post. Who knows what the Times will do, but it should dump the dumb system, which only irks readers and, I assume, its imprisoned star writers.)

And for the hyper-elite crowd, there are still all kinds of premium content that can be charged for to accompany the free site. In addition, business networking tools and other features could be ladled on (why in the world is Facebook, and not The Wall Street Journal, the de facto social-networking site right now for Silicon Valley, for example) to create a very loyal and high-level audience.

I could go on, but why not let Murdoch, who floated one of the more intriguing ideas in a very interesting interview he did with Time in late June before he won his quest to nab Dow Jones:

“What if, at the Journal, we spent $100 million a year hiring all the best business journalists in the world? Say 200 of them. And spent some money on establishing the brand but went global–a great, great newspaper with big, iconic names, outstanding writers, reporters, experts. And then you make it free, online only. No printing plants, no paper, no trucks,” he said. “How long would it take for the advertising to come? It would be successful, it would work and you’d make … a little bit of money. Then again, the Journal and the Times make very little money now.”

Ouch. But what-if indeed, especially if Murdoch is footing the bill to find out?