BoomTown's Short List of Yahoo CEOs (Sorry Jerry, but Fortune Favors the Prepared)

Billionaire activist investor Carl Icahn has asked for it, although he has gone all kittenish now, after realizing his scheme to get Microsoft (MSFT) to buy Yahoo (YHOO) was over, once Yahoo signed on with Google (GOOG) to outsource some of its search-ad business.

And then the New York Times’s Joe Nocera called for it in an eviscerating column this past weekend that articulated what an increasing number of people in Silicon Valley and Wall Street and, more importantly, within Yahoo have been thinking of late.

And that it is: Whether Yahoo CEO Jerry Yang (pictured here at D6) should step down in favor of another top executive to lead the troubled Internet company into the next era.

It’s the obvious question, of course, to ask whether the co-founder of Yahoo has what it takes to manage the company through what will doubtlessly be a very difficult year.

(Speaking of that, see this disturbing hiring freeze post by Peter Kafka of Silicon Alley Insider, which might spell trouble ahead at Yahoo.)

BoomTown asked Yang specifically why he was the right leader for Yahoo going forward at our sixth D: All Things Digital conference recently and–guess what?–he did not really have an answer to the question.

Let me for him, then: The main reason he is the right leader is due to his history, his obvious love for Yahoo and its employees and that his heart, as Yang said in his one and only passionate moment onstage, does bleed Yahoo purple.

Unfortunately, as important and touching as those things are, it’s probably not enough for the rough road ahead for Yahoo.

As Yahoo continues to be in limbo, pressure is sure to mount heavily on Yang, and it is not a stretch to imagine he will not remain in the top job at the troubled company for the long term.

So who would be good to replace him?

The list is a long one and could include execs like Tim Armstrong of Google, Kevin Johnson of Microsoft and any number of media and advertising execs.

But I have six candidates I like, so here’s my short list, in no particular order (and remember, the last time I made one for the job of the No. 2 leader for Facebook, its current COO Sheryl Sandberg was high on my list).

Sue Decker

Yahoo President Sue Decker (pictured here) is the obvious choice for Yang to hand over the reins to.

But should he?

Here are the positives: Decker is smart, articulate, financially savvy and a well-known quantity within Yahoo.

And, like Yang, she has worked her heart out there for many years.

But there are some significant negatives, starting with the tarnish of the whole Microsoft takeover saga, which most think both she and Yang have handled badly.

After so much confusion and missed opportunities, it is not clear if the troops at Yahoo or, perhaps more importantly, Wall Street and the company’s shareholders will give Decker the kind of running room she needs.

In addition, again and again, many within Yahoo talk about Decker’s lack of product feel and overall vision that will be required to truly give Yahoo the kick in the pants it so sorely needs.

Plus, Decker has been around Yahoo a long time and is clearly part of the leadership group that has allowed the company to languish for so long.

Nonetheless, Decker clearly remains the front-runner and might blossom if she had full control over Yahoo, as Bob Iger of Disney (DIS) did there, for example.

Meg Whitman

While many do not know it, Meg Whitman (pictured here) was almost the CEO of Yahoo once, but lost the chance due to a botched merger attempt between Yahoo and eBay (EBAY) back in Web 1.0.

Think of the might-have-beens of that union.

There is no doubt Whitman is an Internet exec star, despite the fact that she herself admits having done as much as she could at eBay after a decade when she recently stepped down as CEO there.

But that kind of candor is exactly what is most impressive about Whitman, who is straight-talking, and very, very tough, despite a sunny-seeming exterior.

She has certainly impressed Yahoos already, having appeared in the not-too-distant past at a sales conference, where she blew away the crowd with her grasp of Yahoo’s business.

Here’s the problem: Most expect the Republican Whitman to make her next move in the California political arena. Can you say Governor Whitman? Senator Whitman?

And also, she’s about as rich as you can be and any monetary attraction to reviving Yahoo would probably be negligible.

Peter Chernin

Let’s be clear–we’re not putting Peter Chernin (pictured here and BoomTown’s kind-of boss) in this list to kiss up to him.

While News Corp. (NWS), where Chernin is No. 2, is the owner of this site, I and many others consider him (along with Disney’s Iger) to be one of the sharpest and most versatile “old” media execs to get the Web.

At the very least, he does not seem scared senseless by it. (Which is a very big deal.)

And while he probably presides over one of the choicest media conglomerates out there, CEO Rupert Murdoch shows no signs of retiring, and his son, James Murdoch, is clearly training in the wings.

A move to Yahoo would be a bold one for someone like Chernin, who clearly has the tough management chops to run the place and give it direction to become a true partner to Hollywood in the way the Spock clones of Google never ever will be able to.

Actually, given he has a foot in both old and new media (Hulu.com, MySpace), he is BoomTown’s No. 1 pick.

Marc Andreessen

I had included Marc Andreessen (pictured here) in my list as a possible No. 2 exec at Facebook as a bit of a lark, just to remind folks that vision matters.

For his excellent blog alone, Andreeseen deserves a lot of attention for its bracing insight about the Internet business and its future.

And Andreessen has plenty of real-life chops too, from his founding Netscape right up until today, creating a series of new Web companies (he is currently chairman of a social-networking company called Ning) and investing in a lot of others that have given him a lot of gravitas and financial windfalls over the years.

Let me clearly state, I was not sure Andreessen could ever grow out of his enfant-terrible mode when I covered him several years ago, but that has clearly happened.

He knows how to build exciting companies, he is well-liked in Silicon Valley, he knows about scale, he knows about social networking and he is a respected technologist.

Most of all, Andreessen would be a leader who would add a lot of excitement to Yahoo. And, believe me, Yahoo needs a lot of that.

Dan Rosensweig

I know, I know. But why not?

Some might question my choice of Dan Rosensweig (pictured here), mostly because he departed from Yahoo in a previous crisis, but was still part of the management group that got Yahoo into this mess in the first place.

But, think hard. Rosensweig was not in charge then–in fact, leadership failures fell to former CEO Terry Semel and also Yang.

In addition, many at Yahoo–though not all–thought Rosensweig did a decent job of running the place.

He also wanted Yahoo to take a lot more chances than it did and is well liked in Silicon Valley and Wall Street.

In leaving and then returning, Rosensweig might represent a choice that allows Yahoo employees to feel confident that some of its past soul remains.

Mark Cuban

I am not kidding. Not even one little bit.

I know Mark Cuban (pictured here hoofing with gusto) is disliked by Yang and others at Yahoo for selling Broadcast.com to Yahoo back in the last bubble and then clearing out and making bank.

And I know they were furious that Cuban popped up on Icahn’s alternative board to replace Yahoo’s current board.

So what! Big whoop! Blah, blah, blah.

Because Yahoo needs a major restart and Cuban would easily be able to push that button.

Cuban is unorthodox, has clear business acumen and success, knows how to invest and he is loaded for bear with vision.

He is also dabbling in some very interesting arena of HDTV, as well as being involved in some other interesting investments.

Cuban is willing to be controversial and often takes aim at Google, with some good results, in his blog.

His current post: “Hulu Is Kicking YouTube’s Ass.” (Ahahahahahaha. Dang, I wish I had written it.)

It’s that kind of moxie that means he is probably the only one with the guts to really get down in the weeds of Yahoo and start hacking away at the tangle that needs hacking.

Also, Cuban can sure dance.

And, most of all, the next CEO of Yahoo is going to need to know how to do some very complex two-stepping–with Wall Street, with shareholders and with employees.

And he or she is going to have to look good doing it.

Please see this disclosure related to me and Google.