The Ricketts family has agreed to buy the Chicago Cubs franchise for close to $900 million. The deal includes the baseball team, Wrigley Field, and a 25% stake in Chicago's regional sports network. The deal is expected to close within 60-90 days.

The Ricketts family fortune comes from its patriarch J. Joe Ricketts who founded TD Ameritrade (NASDAQ: AMTD), and is expected to be sufficient to remake the perennial also-rans into legitimate contenders.

While Sam Zell's sale of the team was made more urgent by the declining fortunes of Tribune and its huge debt load that led to bankruptcy, the Cubs don't appear to be selling at a firesale price. Back in April Forbes estimated the team's value at $642 million, including the stadium. But Forbes added that "The new man in charge at Tribune is Samuel Zell, who will likely sell the Cubs to reduce debt, for between $650 million and $1.3 billion, depending on whether or not 94-year-old Wrigley Field and Tribune's 25% stake in local sports cable channel Comcast SportsNet Chicago are included."

The offer was made more attractive by the fact that it was 50% cash, substantially more than other competing bids. With the debt markets the way they are right now, offers contingent on financing are not especially compelling.

The Cubs haven't won a World Series in 101 years, but they may have just taken a big step toward that goal.

When Tribune Co. (OTC: TRBCQ) owner Sam Zell took the publishing and media giant private about a year ago, little did he know that his move would completely backfire, leading to a bankruptcy just under a month ago. With way too much debt, one of the nicer possessions in Zell's closet has been the Chicago Cubs. Outspoken billionaire Mark Cuban wants to buy them, but at a discount to Zell's asking price of course.

Cuban's balking at the approximately $1 billion price tag that seems to be the asking price for the Cubbies. Cuban probably is thinking that Tribune and Zell are in such dire straights that he can hold out a bit and score the Cubs for a much lower price -- perhaps $600 million or so. Zell, who is going to have to generate some asset sales regardless of how Tribune navigates through bankruptcy, needs to make this sale. In fact, all of the flash wrapped up in Tribune's assets that don't have a core function in its business probably will have to go. Time for egos to take a vacation.

Tribune Co. was for a time a great collection of media assets. Just like any other newspaper publisher, it was caught off-guard when most news seekers turned to the internet for instant news -- not late news like newspapers generally supply. Local content and freshness has been what has saved many publishers, but who knows if this will last.

For now, Zell's huge misstep with Tribune is going to demand he bite his tongue and rake in some cash. It's nice to know that two outspoken rich guys will be the ones getting to deal with each other soon, and perhaps Cuban will use his blog to chip away at the Cubs' price even more.

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

When Sam Zell acquired the Tribune Co. in April 2007 for $8.2 billion in cash, pundits speculated about whether the "grave dancer" who had made billions in distressed real estate had bitten off more than he could chew. The overwhelming evidence indicates that is exactly what happened.

Even by the very low standards of the newspaper industry, Tribune was a disaster. Many of its papers were big-city dailies that have been hit especially hard from the move by advertisers online. The Los Angles Times, the flagship paper of the old Times Mirror chain, experienced both the biggest declines in circulation and in newsroom employees, according to a New York Times report from October. During the third quarter, operating expenses in the publishing business rose 6% to $640 million while operating revenue plunged 13% to $654 million. It's no surprise that there have been boatloads of layoffs in the division.

The broadcasting business has also been hurt by soft advertising at the company's 23 television stations. Mark Cuban's efforts to buy the company's Chicago Cubs have reportedly been held up because the the loud-mouth billionaire's problems with the SEC. The fact that many businesses are finding it impossible to get a line of credit does not help either.

Some big companies have already gone bankrupt. The Tribune Company is the most recent. But, one of the trend's earliest victims was Lehman.

At the economy goes deeper into Hell with each passing month, bankruptcy attorneys will become the richest lawyers in America.

According to MarketWatch, "A sour economy and tight credit market clearly are just the right ingredients to bring about a wave of bankruptcies." There is no shame in it. Airlines have been doing it for decades.

Chapter 11 is actually a nifty way to stiff debt holders and employees. If a company can find an investor who wants to gamble they can get most of a bankrupt firm's assets in court, a debtor-in-possession, a judge can void loans and employment contracts in the name of keeping a troubled firm alive.

All of that may be good for the operations who seek court protection, but the trend would do further damage to the economy. Many of the firms who financed companies that are in trouble are banks. More losses for them will lead to more write-downs. And, that leads to more shareholder dilution and more government aid. On the employment side, cutting big numbers of people increases joblessness. That, in turn, ratchets down consumer spending and pushes up government costs to support those without work.

Otherwise, Chapter 11 is a great idea for companies in peril.

Douglas A. McIntyre is an editor at 24/7 Wall St.

A lot of America's newspaper companies have been in trouble. Advertising has been down as much as 15% this year and that has gotten worse in the last few months.

Almost all of the chains have had to cut staff and some properties have been put on the block to help the companies pay down debt. But, none of the really big operators in the business have had to go bankrupt.

That may change this week. The Tribune Company, which went private about a year ago, may not be able to make its debt service payments. According to The Wall Street Journal, "Tribune's latest actions underscore the deepening distress enveloping Tribune and other newspaper publishers."

The headline about the Tribune's trouble may be about the newspaper industry, but the story is just as much about the private equity/LBO trend that hit record levels less than two years ago. The Tribune Company was able to borrow almost $12 billion in an industry which was already beginning its downturn. That says a remarkable amount about the level of risk that bankers were willing to take to get fees.

Now, the firms that put the debt into the Tribune transaction are faced with getting pennies on the dollar. Newspapers may be a bad business, but it looks like private equity is turning out to be even worse.

Douglas A. McIntyre is an editor at 247wallst.com

Sam Zell is looking to unload the Chicago Cubs baseball franchise that came with his ill-timed $8.2 billion acquisition of Tribune Media Co., and the most aggressive suitor appears to be dot-com billionaire Mark Cuban. The New York Times reports that he offered $1.3 billion for the the team, Wrigley Field, and the team's stake in Comcast SportsNet Chicago.

But of course, Cuban, who has accumulated $1.7 million in fines during his tenure as owner of the Dallas Mavericks, is not without his critics, to say the least. He's too arrogant, too brash, and not gentlemanly enough, they say. He had trouble cracking into the old boy's network of the NBA, and Major League Baseball is said to be even more reluctant to change.

But if Cuban is the high bidder -- and the league will let him in -- it'll be a great day for the Cubs and for baseball. The team hasn't won a World Series since 1908 but, given Cuban's deep pockets and superhuman competitive drive, the Cubs would likely get the extra boost they need to finally win one. Plus, Cubs and Cuban have the same first three letters, so it's pretty much meant to be.

Baseball has dealt with a lot of scandal lately involving performance-enhancing drugs, and it's about time we added a passionate renegade to the current regime of old bureaucrats. And yes, I'm talking to you Ted Lerner.

Tribune, formerly a public newspaper and broadcast company, lost the publisher of its largest newspaper, the LA Times, and the editor of its flagship, the Chicago Tribune. New controlling shareholder Sam Zell is in trouble, burdened by buyout debt he may not be able to pay.

Most analysts saw another modest drop in newspaper ad revenue this year. It has been much worse than that. At some companies in the industry, ad sales are off nearly 15%. An analyst recently dropped his price target on The New York Times Company (NYSE: NYT) to $8 and said the firm would have to cut its dividend. The stock currently trades at $13.21.

The two public companies which are at most risk for not making it another year are Gatehouse (NYSE: GHS) and McClatchy (NYSE: MNI). Both took on big debt loads buying newspaper properties. Both are seeing operating income chopped by falling sales. Either could hit debt service problems which could force them to sell properties of file for Chapter11.

Gatehouse dropped as low as $1.11 in the last few days. Its 52-week high is $19. McClatchy is down to $4.93 from a 52-week high of $28.65. Gatehouse is the most troubled with a high dividend and $1.3 billion in long-term debt.

Newspapers companies have gone from being in a tight spot to being candidates for liquidation. They are a short-seller's dream.

Douglas A. McIntyre is an editor at 24/7 Wall St.

The Tribune is not a public company anymore, but CEO Sam Zell says enough about his plans that it might as well be.

According to The New York Times, Zell "announced a set of deep cuts, saying that shrinking revenue left them no choice." One of the things that means is fewer pages devoted to news as newsprint use is reduced.

The Tribune carries a lot of debt, so it is in more trouble that other chains such as The New York Times Company (NYSE: NYT) and Gannett (NYSE: GCI). But, other large paper operations including McClatchy NYSE: MNI) and Gatehouse (NYSE: GHS) also have massive debt burdens from money they borrowed to expand their empires.

What all of this means is that more reporters and editors will lose their jobs and the typical reader will get a newspaper that is thin as toilet paper. For newspaper company investors it means that stocks, some already down 50% to 70% in the last year, are going down even further.

The trouble also may spell the end of nearly a century of big papers like The New York Times being the news sources of record. The company recently cut 100 people, most of them from the news operation. Covering major national and international stories is becoming more difficult and at some point it may be impossible.

There is always CNN.

Douglas A. McIntyre is an editor at 247wallst.com.

The special committee set up by Rupert Murdoch to ensure the editorial independence of the Wall Street Journal is about as useful as a referee at a professional wrestling bout. The sad thing is that News Corp. (NYSE: NWS) is paying members of this committee $100,000 a year to let Chief Executive Rupert Murdoch do whatever he wants to do anyway.

A case in point is the abrupt resignation of Managing Editor Marcus Brauchli. The lackeys -- oh, I mean the special committee set up following the Dow Jones acquisition -- felt compelled Monday to issue a press release to show publicly that they were on the case. At least, that's what it tried to do.

"Although our charter does not directly envision a process for dealing with a resignation, Committee members expressed the view that learning of the Brauchli matter after the fact failed to meet the letter and the spirit of the agreement," the committee said in a statement. The committee met with Brauchli alone and was told that "his action was not the result of any problem with editorial interference or attempts to impose an ideological viewpoint. He insisted that News Corp. has been `scrupulous' about the integrity of the paper."

Yeah, right.

Murdoch has meddled in his media properties for decades. No special committee is going to stop his lust for power. Anyone who expected otherwise is either naive or deluded. Murdoch will have no inhibitions of messing with Newsday if he succeeds in buying Newsday from Sam Zell's Tribune Co. because beggars can't be choosers.

To the surprise of no one, the newly private Tribune Co. is probably going to sell Newsday. The once-venerable New York paper, like all metro dailies, has fallen on hard times and Tribune's new CEO and owner Sam Zell has got a mountain of debt to pay down.

According to The Wall Street Journal . Long Island-based Cablevision Systems Corp. (NYSE: CVC) and New York's Daily News as potential buyers. Rupert Murdoch probably would love to buy Newsday and combine it with News Corp's (NYSE: NWS) New York Post, but I am not sure whether the antitrust regulators would allow it. He is trying to merge everything but the editorial staffs of the Post -- never a hugely profitable enterprise -- with Newsday to save money in a joint operating agreement, the Journal says.

After spending $5 billion for Dow Jones, Murdoch needs to pick all of the low-hanging fruit he can. I expect this deal to happen. Maybe it will lead to others for papers that buyers are eager to unload. Perhaps, Murdoch might buy other Tribune papers from Zell such as The Baltimore Sun or Los Angeles Times. As the Australian tycoon showed in chasing Dow Jones, influence matters as much to him as profits. Gaining more big papers furthers that goal at the expense of shareholders.

Sam Zell is one of the best real estate investors around and therefore one of the few people whose prognostications for the housing market are actually worth listening to.

And that's good news because, speaking on CNBC's Squawk Box this morning, Zell had this to say about the housing market: "I think starts have already pretty much bottomed out," Zell said. "I think the housing market this spring will begin its recovery phase."

If the recovery will indeed begin that quickly -- and the bottom has already been reached -- than beaten-down REITs have to be considered for investment.

If you're willing to invest based on the idea that Zell is likely to be right but aren't comfortable picking REITs on your own, Vanguard's REIT ETF (AMEX: VNQ) may be worth a look. After a big drop in 2007, the ETF yields around 5%.

Starwood (NYSE: HOT) is hosting a meeting with sell side community at 7:45 a.m. Eastern time today.

Sam Zell reported a 7.72% stake in HOT on Feb. 4.

Smith Barney says: "We view as a strong vote of confidence in HOT's underlying fundamentals (and asset value) by a sophisticated real estate investor."

HOT overall option implied volatility of 40 is near its 26-week average according to Track Data, suggesting non-directional risk.

Option Update is provided by Stock Specialist Paul Foster of theflyonthewall.com

Just for fun, the newspaper industry that is facing excruciating pressure as news seekers and advertisers flock to the internet, now has another negative catalyst to deal with. The housing slowdown and sharp drop in sales is causing a significant drop in newspaper advertising for real estate, a significant chunk of many small papers' overall revenue.

The Tribune Company saw a 40% year over year decline in its real estate ad sales for November. Gannett (NYSE: GCI) is also looking at a 27% drop.

This short-term revenue drop that's a result of macroeconomic factors could extend into the long-term. When the housing market does rebound, will people go back to newspapers? Or will have the internet continue to make inroads, hastening the decline of newspapers into oblivion.

As bleak as the outlook for the industry looks, several highly-respected investors have made large bets on it. Sam Zell recently acquired Tribune, and Warren Buffett has been a long-term investor in the sector.

For contrarian investors, the industry may be worth a look.

Sam Zell formally completed his buyout of the Tribune Company yesterday. It only cost $8.2 billion and months of difficult negotiations -- but now he can go out and get the pitching his newly acquired Chicago Cubs have long needed to win it all. Well, maybe not. Word on the street is that he plans to sell the Cubs and Wrigley Field for a cool billion as soon as he can.

Zell has made it clear that he plans on allowing the various units within the Tribune Company to stand on their own feet. By his count, there are over 60 entities within the company, and each one needs to strike out on its own. As Zell put it, "As I've said over and over again, there are something like 60 entities in the Tribune Co. and I view it as 60 ways to get lucky."

MAJOR PAPERS:

• The Wall Street Journal's "Deal Journal" reported that Sam Zell's planned buyout of Tribune Company (NYSE: TRB) is contingent on the receipt of a solvency opinion, and that this is the first time they have ever seen a deal dependant on this.
• The WSJ's "Heard on the Street" reported that Countrywide Financial Corporation (NYSE: CFC) may not be out of the woods yet. Despite executives promising a return to profitability, there is still a risk the company may eventually seek bankruptcy protection or "resort to huge sales" of new stock.
• U.S. private equity group JC Flowers "is understood" to have walked away from the auction for troubled bank Northern Rock, the Financial Times reported.
• Rupert Murdoch is shaking up the management of News Corp (NYSE: NWS.A), the Financial Times reported, giving his son, James Murdoch, control over the company's European and Asian operations, and appointing two trusted executives to lead Dow Jones & Company Inc (NYSE: DJ) and the Wall Street Journal.

WEB SITES:

• Barron's Online's "Weekly Trader" said AutoNation Inc (NYSE: AN) looks attractive now, despite hovering near a multi-year low. The company has also been on a slow but steady quest to diversify away from unpopular domestic brands by snapping up luxury and import dealerships.