This post is part of our feature on Money Winners of 2008. See all 20.

Barack Obama became the king of fund raising in 2008, having received a record amount in donations for his presidential campaign in the neighborhood of $750 million, and finishing with over $100 million in the bank. These contributions factored into a winning, grass-roots campaign strategy.

Actually he used a two-prong approach that enabled him to tap into the existing Democratic fund-raising machine attracting large donors through various traditional means, such as banquets and A-list parties. At the same time he was able to play the role of outsider and underdog to rally his grass-roots support among the young and commonly disenfranchised, handshake by handshake, and through a very adept use of the internet. The internet provided a constant source of connectivity with his followers, and allowed his team to respond to any news item with immediacy.

Now, president-elect Obama will be hoping to continue to amaze as he is tasked with guiding a devastated economy on the brink of collapse back to some semblance of equilibrium.

Over the past ten years, eBay (NASDAQ: EBAY)'s CEO, Meg Whitman, has had a love / hate relationship with eBay users. No matter what your personal thoughts are regarding Whitman, you have to give it to her; she did take eBay to levels no one would have dreamed possible just ten years ago.

Well, her tenure at eBay is coming to an end, and her next move is into politics, working high up in Senator John McCain's Presidential campaign.

Back in January, Whitman announced that she would be stepping down from eBay to pursue philanthropy and politics, and her first big step is going to be serving as co-chair of Senator McCain's national presidential campaign.

While we still have not reached the point of McCain being announced the official Republican candidate for the upcoming election, it is all but a forgone conclusion that McCain is going to be the Republican's choice for November's pivotal election in America. After a rocky eight years with George Bush running the show, the Republicans are definitely going to have their hands full with this year's election, and Whitman is coming on board to have a leading role in the campaign's financing and policy development.

Investors who worry about tax increases, socialized medicine and Hillary Clinton picking out fabric swatches, should be petrified by the recent polling data showing how low President Bush's popularity has sunk.

A recent NBC/Wall Street Journal poll showed that by a margin of 52% to 31%, Americans want the Democrats to win the presidency next year. Politico.com is reporting that "Republicans across the country are warning that increasing public discontent toward President Bush, the Iraq war and the GOP brand in general threatens to send the party's 2008 campaign planning into a tailspin."

Even though the economy is fairly strong and the stock market continues to set record after record, Wall Street seems out of step with Main Street. People are fed up with high gas prices, the war in Iraq and the bursting of the real estate bubble.

They also don't like corporate fat cats either, so Blackstone Group LP CEO Steve Schwarzman, who stands to earn as much as $677 million from the private equity firm's upcoming IPO, might want to watch how he spends his money before the election. For instance, he should avoid lighting cigars with $100 bills.

Members of Congress are already grousing about the favorable tax treatment that hedge funds and private equity companies enjoy, which was underscored by the Blackstone IPO. There will be more and more complaining about private equity and hedge funds over the next few months.

In fact, there will be such noise about issues of interest to investors ranging from taxes to free trade that it will be difficult to figure out what to believe.

About the only thing that's for certain is that big changes are coming.

Presidential candidates are trying to lure voters on News Corp.'s (NYSE:NWS) MySpace site, showing that they will go to any lengths to feign interest in the concerns of America's youth.

Next up, John McCain will try out for the X games. Hilliary Clinton will dive into a mosh pit while Barack Obama woos voters playing "The Second Life." Mitt Romney seems a bit straight-laced for anything extreme. He's going to have to learn how to skateboard.

The Web will be a key battleground for the 2008 presidential election. Howard Dean paved the way for this though the enthusiasm of his Internet supporters didn't translated into enough real-world voters. Both Democrats and Republicans, though were stunned by how much money Dean raised over the Web.

Since the country is pretty even divided, every constituency there is a going to be a big fight for every demographic even young people, most of whom don't bother voting. This is going to be a boon for MySpace and Google Inc.'s (NASDAQ:GOOG) YouTube though it's unclear how much profits they will make from political spending.

But candidates need to be careful. Internet popularity can be fleeting. Thanks to the Web, there's no hiding from mistakes. Gaffes, mi statements and other errors spread on the Web faster than speed of spin.

When I first read this article from CNN Money.com, regarding the Obama/Edwards tag team against Wal-Mart Stores, Inc. (NYSE:WMT), my brain yelled, "Huh? What? Who?"

What are two liberal socialist Democrats doing taking potshots at Wal-Mart of all things? Egads, couldn't they even wait until after Christmas before tossing their first '08 presidential campaign grenade?

Illinois senator Barack Obama(D) and former Democratic vice presidential hopeful John Edwards, drew the sword Wednesday along with Wal-Mart watchdog group WakeUpWalMart.com to denounce Wal-mart Corporation regarding the treatment of their employees. The two politicians had to "back door" their appearance by going through the union assembled public group because it is perhaps bad form and too controlled to directly address the union through normal channels. The entire event was obviously exploited by Obama and Edwards in an attempt to gain increased appeal to the minimum wage sector.

I'm not a big fan of Wal-mart, but I don't like this political pawn pushing either. If Obama and Edwards are looking for grassroots brownie points, they've picked a pretty rude way to get them.