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.

General Motors Corp. (NYSE: GM) and Ford Motor Co. (NYSE: F) soared about 19% each in Frankfurt as Congress is getting closer to approve a bailout for the Big 3 automakers. The White House and Democratic congressional leaders are narrowing their differences and could agree on a deal and bring to a vote soon. Both shares are trading 21% and 18% higher respectively in premarket (8:12 am). By midday, both automakers' stocks were up about 14%.

Other gainers in Frankfurt include oil and gas producers, commodity stocks and financials: Alcoa Inc. (NYSE: AA) jumped 10%, Bank of America (NYSE: BAC) shares rose 11% and Exxon Mobil (NYSE: XOM) gained about 5%. In premarket, AA shares are 6.4%, 5% and 2.4% higher (8:15 am). Commodities, industrials, financial and oil & gas stocks continued to gain well throughout the session with Alcoa up 14% by midday and BAC up 11%. XOM was only up 2.5% thought.

Tribune Co. may file for Chapter 11 bankruptcy protection as soon as this week, according to sources of The Wall Street Journal, as the newspaper industry worsens.

Hartford Financial (NYSE: HIG) shares are continuing their massive upward trend from Friday after the insurer raised its full-year operating profit forecast and said the capital outlook at its insurance units was strong. Shares are up 13.4% in premarket trading. HIG stock had simiilar gains by midday trading.

After shareholders had approved on Friday Bank of America's takeover of Merrill Lynch (NYSE: MER), Merrill's CEO John Thain has suggested to directors that he get a 2008 bonus of as much as $10 million. According to WSJ sources, the company's compensation committee is resisting his request.

MAJOR PAPERS:

• The Wall Street Journal reported that a spokesperson for New Corporation (NYSE: NWS) said the company has dropped out of the bidding for Tribune Co's (NYSE: TXA) Newsday. This leaves Cablevision Systems Corporation (NYSE: CVC) as the apparent winner of the auction.
• According to people familiar with the matter, the Wall Street Journal reported that American International Group Inc's (NYSE: AIG) airplane-leasing unit is considering a split from the company. The people said International Lease Finance Corp have grown "increasingly concerned" the company will be hurt by AIG's financial troubles.
• Royal Dutch Shell Plc (NYSE: RDS.A) and Spain's Repsol YPF SA (NYSE: REP) are pulling out of one of Iran's biggest gas projects, the $10B-plus development of phase 13 of South Pars, the world's largest gas field, the Financial Times reported.

WEB SITES:

• Bloomberg reported that HSBC Holdings Plc (NYSE: HBC) set aside a smaller-than-forecast $3.2B for bad loans in the U.S. The bank also said its Q1 profit was higher than Q107.

MAJOR PAPERS:

• The Wall Street Journal reported that in a list released last night by the FCC, Google Inc (NASDAQ: GOOG), Cablevision Systems Corporation (NYSE: CVC) and other "nontraditional" players are set to compete against more traditional wireless companies like Qualcomm Incorporated (NASDAQ: QCOM) and MetroPCS Communications Inc (NYSE: PCS) in the federal government's spectrum auction next month.

OTHER PAPERS:

• Banks that include Merrill Lynch & Co Inc (NYSE: MER) and The Bear Stearns Companies Inc (NYSE: BSC) are reportedly in talks to help bail out struggling bond insurer ACA Capital Holdings, which lost $1B in the most recent quarter, according to two people briefed on the situation and reported by the New York Times; ACA Capital has guaranteed $26B in mortgage securities.
• Executives at Tribune Company (NYSE: TRB) were faced with last-minute questioning from bankers that were reluctant to fund the final portion of the $8.2B deal to take the company private, according to sources close to the company, the Chicago Tribune reported.

WEB SITES:

• Barron's Online's "Inside Scoop" reported that analysts are not convinced that the deal with Citadel is enough to save E*Trade Financial Corporation (NASDAQ: ETFC), as it does not eliminate E*Trade's $12.4B second-lien mortgage exposure, and the company could potentially face further customer attrition, which many think will continue to pressure the shares.

Tribune Co. (NYSE: TRB) shares are rising this morning as the U.S. Federal Communications Commission is expected to approve a measure that will ease restrictions on media ownership. The plan would lift a ban in the twenty largest American cities restricting media outlets from owning a newspaper, and a television or radio station in the same market.If you think that the company won't fall by too much in the coming months, then now could be a good time to look at a bullish hedged trade on TRB.

After hitting a one-year low of $22.78 in August, the stock has hit a new one-year high of $33.40 today. TRB opened this morning at $33.37. So far today the stock has hit a low of $33.09 and a high of $33.40. As of 11:05, TRB is trading at $33.28, up 99 cents (3.1%). The chart for TRB looks bullish and steady, while S&P gives the stock a neutral 3 STARS (out of 5) hold rating.

For a bullish hedged play on this stock, I would consider a February bull-put credit spread below the $27.50 range. A bull-put credit spread is an options position that combines the purchase and sale of put options to hedge risk in case the stock doesn't do what you think but still leverage nice returns. For this particular trade, we will make a 4.2% return in just 2 months as long as TRB is above $27.50 at February expiration. Tribune would have to fall by more than 17% before we would start to lose money.

TRB hasn't been below $27.50 since October and has shown support around $29.50 recently. This trade could be risky if the stock breaks its upward trend, but even if that happens, this position could be protected by support the stock has formed around $31 over the past week. Plus, TRB might find some support at its 200 day moving average, which is currently at $30 and rising.

Brent Archer is an options analyst and writer at Investors Observer. At publication time, Brent neither owns nor controls positions in TRB.

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.

Tribune (NYSE: TRB) is recently up $32.08.

CNBC's David Faber says the TRB deal could close very soon. TRB has expected its $34 per share sale to Sam Zell, private equity, debt holders and employees to be closed by year-end. The FCC granted temporary waivers to complete the deal. TRB announced this morning it intends to use cash on hand to reduce total amount of bridge loan to $1.6 billion from $2.1 billion. TRB January option implied volatility of 33 is below a level of 79 from Dec 6th and below its 26-week average of 38 according to Track Data, suggesting the close of the $34 deal is near.

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

Tribune (NYSE: TRB) is recently down 55 cents to $29.95. TRB expects its $34-per-share sale to Sam Zell, private equity, debt holders and employees to be closed by end of 2007. The FCC granted temporary waivers to complete the deal on Dec. 30. TRB call option volume of 2,688 contracts compares to put volume of 15,775 contracts. TRB December option implied volatility of 80 is above its 26-week average of 36 according to Track Data, suggesting larger price risks.

LDK Solar (NYSE: LDK) is a manufacturer of multicrystalline solar wafers. Dow Jones reported LDK will tap $700 million in long-term debt and credit lines, as well as about $100 million in customer prepayments. LDK auditing report on the investigation of allegations of inaccurate inventory is expected in early December. LDK has said the company has correctly reported its inventories. LDK is expected to report Q3 EPS in mid-December. LDK December option implied volatility is at 165 and March is at 133; above its 21-week average of 98, according to Track Data, suggesting larger risk.

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

TheStreet.com's Jim Cramer says if any of your holdings in this sector have too much of any one kind of credit, use current market strength to sell.

Getting our arms around the problem. That's the real way we get closure on this credit problem. That's why the market was able to rally Tuesday, even though no one says the problem is getting better.

At last we're just trying to figure out how bad it can be because we know it is worse than the $42 billion that has already been charged off in subprime. By the way, even that figure, which seems staggeringly high, is only a fraction of the $250 billion minimum number I am using.

What's so maddening is that there isn't one kind of debt problem. There are three kinds of debt, with a subset for the worst kind. You have to run the gauntlet of all three kinds if you are going to be blessed by the market. And so far, only Goldman (NYSE: GS) (Cramer's Take) has done that.

Most mergers are driven by the notion, sometimes wildly mistaken, that the combination will bring both a competitive advantage. Some pairs of companies, however, seem so intuitively right for one another, no bottom-line considerations should be allowed to interfere with their matrimony. Like a foul ball and a plate glass window, these two were meant for one another.

Pity the poor Chicago Cubs fan. The modern Sisyphus has spent a century coaxing his baseball team to the verge of greatness, only to see it collapse into a pile of baseline chalk time after time. The 2007 season was especially painful, after investing $136 million in slugger Alfonso Soriano and inking one of the game's best managers, Lou Piniella. The team eked into the playoffs, only to be swept in three games by the Arizona Diamondbacks.

The Cubs are part of The Tribune Company (NYSE: TRB), currently in the process of being bought by Sam Zell. Many expect the Cubs to be sold when/if this deal is completed.

Given that the Cubs have provided a century of heartbreak to the windy city, perhaps the team should merge with a company that can make money off of fans' paroxysms. Emergency Medical Services (NYSE: EMS) could be such a partner.

MOST NOTEWORTHY: Apollo Group, Zoran, AmSurg Corp, Apple and Tribune Co were today's noteworthy upgrades:

• Baird upgraded shares of Apollo Group (NASDAQ: APOL) to Outperform from Neutral based on positive enrollment and revenue trends, margin improvement, and a strategic international announcement.
  
• CIBC upped its rating on Zoran Corporation (NASDAQ: ZRAN) to Sector Outperformer from Sector Performer following strong Q3 results and guidance.
  
• Jefferies upgraded shares of AmSurg Corp (NASDAQ: AMSG) to Buy from Hold as they believe the new CEO is preparing to drive earnings growth through acquisitions.
  
• ThinkEquity continues to expect Apple (NASDAQ: AAPL) to outpace the industry in growth. The firm upgraded shares to Buy from Accumulate.
  
• Barrington upgraded shares of Tribune Company (NYSE: TRB) to Market Perform from Underperform on valuation, as they believe the current price significantly discounts the risks of the going private transaction getting done.

OTHER UPGRADES:

• Citigroup upgraded Jarden Corporation (NYSE: JAH) and Teradyne (NYSE: TER) to Buy from Hold.
  
• Lehman upgraded SunPower Corporation (NASDAQ: SPWR) to Overweight from Equal Weight.
  
• HSBC upgraded ArcelorMittal (NYSE: MT) to Overweight from Underweight.
  
• WestLB raised Roche Holding (OTC: RHHBY) to Add from Hold.

Many people are puzzled over Sam Zell's highly leveraged $8.2 billion purchase of the Tribune Co. in light of the decline in the newspaper business. One of the diamonds in the deal, however, is the Chicago Cubs, and indications are that he intends to quickly mine that gem for all it's worth.

According to the Los Angeles Times, the Tribune Co.'s (NYSE:TRB) avowed intention to sell the Cubbies may be considerably more complex than most franchise sales. The Tribune owns not only the ball club, but also the ballpark, and 25% of the cable TV network that carries its broadcasts, and could choose to sell them separately.

The Cubs, despite a century-long title drought, continue to draw capacity crowds to legendary Wrigley Field, over three million last year alone. This year, to the surprise of most prognosticators, the team is fighting for the NL Central pennant, great timing for the sellers. According to Forbes, the team alone is currently worth $592 million, on an operating income of $22 million.