Friday could be the day former NBA star Charles Barkley makes good on a $400,000 gambling debt to casino operator Wynn Resorts (WYNN). Barkley lost the money at the Wynn Las Vegas resort in October, the resort claimed a civil complaint filed Wednesday in Nevada state court. In the complaint, Wynn said Barkley -now  a broadcaster at Turner Network Television, which is owned by Fortune’s parent, Time Warner (TWX) - hadn’t responded to “repeated demands” for repayment. The complaint spurred Clark County District Attorney David Roger to say prosecutors would file a criminal complaint if Barkley didn’t pay. Barkley then told the Associated Press at a golf tournament in Alabama that the debt stemmed from a wager on the 2008 Super Bowl, and that he intends to pay Wynn back. “My mistake,” Barkley said, the AP reports. “I’m not broke, and I’m going to take care of it.”

But as of Thursday night, Barkley still hadn’t set matters straight with the authorities, the Las Vegas Sun reports. The paper reports that Barkley has to make arrangements with the Clark County district attorney’s bad check unit - and that he hadn’t done so as of the close of business Thursday.  “We’ll welcome his phone call,” said Roger. “We’re open 8 to 5.”

Disclosure: TNT is owned by Time Warner (TWX), also a parent of CNNMoney.com and Fortune.

MBIA (MBI) posted another big loss. The bond insurer lost $2.4 billion, or $13.03 a share, for the first quarter ended March 31, compared with the year-ago profit of $199 million, or $1.46 a share. The latest quarter included a $3.6 billion mark-to-market writedown on MBIA’s insured credit default swap portfolio. The news, which follows a $2.3 billion fourth-quarter loss, comes a week after CEO Jay Brown insisted the company doesn’t need new capital and warned shareholders that the company was struggling to arrive at a valuation for the insured credit default swap portfolio. “I can tell you with great certainty that no two people could ever agree on this calculation,” he wrote, “so don’t be surprised when external sources propose wildly different possibilities for MBIA.” Brown is due to host a conference call at 2 p.m. EST, so the external sources may have their say then. MBIA shares fell 12% in early trading Monday to $8.30.

Here’s something you don’t see every day: A company hit by housing-related losses announces a massive quarterly loss and a plan to raise billions of dollars of new capital - while increasing its dividend.

That was the news out late Thursday at AIG (AIG), the insurance company locked in a fight to the death with longtime former CEO Hank Greenberg. AIG said it lost $7.8 billion, or $3.09 a share, for the quarter ended March 31, as “weak U.S. housing market, the disruption in the credit markets, [and] equity market volatility had a substantial adverse effect on its results.”

To make up for the massive loss, AIG said it would raise $12.5 billion in new capital, first through a $7.5 billion sale of common stock and equity-linked units, and then through a later $5 billion issuance of “high equity content fixed income securities.”

“These offerings are designed to further strengthen AIG’s significant financial resources,” the company said, “and will enhance its ability to grow while maintaining the strength to withstand potential short-term market volatility.”

That all sounds pretty standard. But if AIG wants to strengthen its resources, why is it boosting its quarterly dividend by 10%, to 22 cents a share? Many other companies hitting shareholders up for new capital, such as Citi (C) and Fannie Mae (FNM), have slashed their payouts in a bid to preserve cash. Perhaps AIG is trying to show investors that it believes the upheaval in the markets is temporary and that the company is still operating from a position of strength. But Thursday’s quarterly loss report - including a $3.6 billion operating loss, excluding investment gains and losses - makes that argument seem a bit far-fetched. Shares fell 8% in postclose trading.

Fannie Mae (FNM) is tightening its belt. The big mortgage lender said Tuesday it would cut its quarterly dividend and raise $6 billion in new capital to replenish its accounts after its latest quarterly loss. Fannie lost $2.2 billion, or $2.57 a share, for the quarter ended March 31, reversing the year-ago profit of $961 million, or 85 cents a share. The latest quarter was hit by a sharp rise in credit costs,  Fannie said in a filing with the Securities and Exchange Commission. Its shares dropped 13% in early trading Tuesday.

“During the first quarter we saw heightened volatility in the secondary mortgage market, credit spreads that widened out to 22-year highs, and home prices that fell faster than expected,” said CEO Daniel H. Mudd. “Our first quarter results, although an improvement over the last quarter, reflect these challenging market conditions.” The latest quarter included $4.4 billion in fair value losses, reflecting markdowns on the value of Fannie’s derivatives holdings and trading positions.

The announcement comes just a day after Fed chief Ben Bernanke called on Fannie and sibling Freddie Mac (FRE) to play a bigger role in easing the pain of the U.S. housing bust. Fannie said in its filing Tuesday morning it will “announce a series of new initiatives called ‘Keys to Recovery’ on its Tuesday earnings conference call. The plan, which includes the refinancing of underwater loans, “is geared toward providing liquidity, stability and affordability to the housing and mortgage markets for the long term, keeping struggling borrowers in their homes, assisting prospective homebuyers with home purchases, and stabilizing communities affected by the mortgage market downturn,” the company said.

In part, the decision to raise new capital reflects both the declining health of the mortgage market and Fannie’s expanding role in treating those ills. Fannie said the capital-raising plan - which includes $2 billion in common stock and $2 billion in each of two classes of preferred stock - and the dime-a-share dividend cut, to 25 cents a share, will enable it “to operate and grow from a position of strength.” Judging by Tuesday’s market reaction, though, investors aren’t so sure.

Legg Mason (LM) is reeling. The Baltimore-based asset manager swung to a first-quarter loss of $256 million, or $1.81 a share, from the year-ago profit of $173 million, or $1.19 a share. The latest quarter was hit by $206 million in charges tied to the company’s decision to support money-market funds that suffered losses after they invested in illiquid structured debt, and a $95 million hit in a wealth management unit. Revenue fell 6% from a year ago to $1.07 billion. Analysts were looking for a 27-cent loss on revenue of $1.12 billion.

“This past quarter was among the most difficult we have ever faced and we are disappointed with our results,” said CEO Mark Fetting. “We remain a fundamentally strong firm today, but we know we have work to do.”

Indeed, assets under management fell 5% from a year ago to $950 billion, as the company’s portfolio suffered market losses of $28 billion and customer cash outflows of $19 billion.  Equity outflows were $17 billion and fixed income outflows were $7 billion for the quarter, while liquidity inflows totaled $5 billion.

“We have major managers who are performing very well in a tough investment climate, and we are seeing growth outside the U.S.,” Fetting said, “but we know that we need our U.S. equity managers to return to form, and this is a top priority.”

Among the managers who need to return to form is Legg Mason Value Trust manager Bill Miller, whose fund lost 20% of its value in the first quarter after bad bets on struggling financial firms such as Bear Stearns (BSC) and Countrywide (CFC). The losses haven’t curbed Miller’s appetite for publicity, however. A day after he called on Yahoo (YHOO) to buy back stock, he told Bloomberg in an interview that he expects Microsoft (MSFT) to come back to the table with a new offer for the Internet giant - though perhaps not for a while. “If I’m sitting in their shoes, I’ll go away and see what happens,” Miller said of Microsoft. “I can come back and the worst case is, I’ll pay six months more of my free cash flow.” 

Fed chief Ben Bernanke sees a big role for Fannie Mae (FNM) and Freddie Mac (FRE) in resolving the U.S. housing crisis. Speaking at a Columbia Business School dinner Monday night, Bernanke said the government-sponsored mortgage investors should “move quickly to raise significant new capital” to aid the housing market, Bloomberg reports. Bernanke also spoke in support of proposals that would have lenders forgiving parts of struggling homeowners’ loans and make Federal Housing Administration refinancings more widely available.

Calls for new capital at the big mortgage companies are nothing new. The director of Fannie and Freddie’s main regulator, James Lockhart of the Office of Federal Housing Enterprise Oversight, said in March that the companies may raise as much as $20 billion in new capital as part of a deal freeing them to expand their purchases of mortgage securities. The firms raised some $15 billion at the end of 2007 via preferred stock sales to replenish their coffers after two quarters of hefty losses tied to souring mortgages. Fannie Mae’s first-quarter earnings, due out Tuesday morning and expected to show a third straight quarterly loss, may offer a clue as to how much money the firms will need to raise.

Bad news for Wall Street means more business for BlackRock (BLK). The New York-based asset manager is in talks that could lead to its managing a fund made up of subprime mortgage-related assets being cast off by Swiss bank UBS (UBS), Bloomberg reports, citing two people with knowledge of the discussions. UBS said last month it would put its U.S. residential mortgage assets into a separate workout unit to provide “the greatest opportunity for shareholders to realize value over time.”

The news comes as UBS is preparing its first-quarter earnings report, which is due out Tuesday morning. Along with a writedown-heavy first-quarter loss of more than $11 billion, UBS is expected to lay out plans for thousands of job cuts as the bank reverses years of headfirst expansion.

A UBS assignment would only extend BlackRock’s already substantial impaired-assets business. The firm is managing a portfolio of BearStearns (BSC) assets that were cast aside by JPMorgan (JPM) back in March when the Fed oversaw a rescue of the cash-strapped brokerage firm. CEO Larry Fink said on BlackRock’s first-quarter conference call last month that the firm expects to see investors moving into distressed mortgage-related assets in coming months as fund managers and other yield-minded buyers move back into private-label securities from the safety of Treasuries. When they do, it appears BlackRock will have a number of options for them to look at.

Countrywide (CFC) sank 11% in morning trading Monday after an analyst said Bank of America (BAC) should walk away from its $4 billion deal to buy Countrywide, due to rising credit costs and souring loans at the troubled mortgage lender. Analyst Paul Miller at Friedman Billings Ramsey downgraded Countrywide to underperform from market perform and cut his price target to $2 from $7, saying Bank of America could face writedowns of $30 billion or more when it closes the Countrywide deal. He says BofA’s statement Thursday that it won’t guarantee Countrywide debt “is most likely the first step in renegotiating the entire deal.”

Miller estimates that Bank of America has a $22 billion cushion to absorb writedowns of Countrywide’s loan book. While that sounds like a big number, the analyst lays out a worst-case scenario that could see Bank of America taking $17 billion in writedowns on Countrywide’s home equity and second mortgage portfolio alone. The analyst says writedowns could reach $11 billion on Countrywide’s portfolio of option adjustable-rate mortgages (ARMs) and $5 billion on hybrid ARMs and other loans. Writedowns of that size could easily swamp the cushion Bank of America set aside when it agreed back in January to buy Countrywide for $7 or so in BofA stock.

“The issue of fair value marks was a significant part of the reason that National City (NCC) failed to find an acquirer,” Miller writes, referring to the Cleveland-based bank, which has taken large mortgage-related losses. “If fair value marks sufficiently exceed BAC’s projections at the time of its due diligence, we believe the deal price for the purchase of CFC could be renegotiated lower, or BAC could (and should) decide to walk away.”

A sobering fourth-quarter report from Centex (CTX) shows why the Fed’s rate-cutting days probably aren’t over. The Dallas-based homebuilder lost $908 million, or $7.34 a share, from continuing operations in the latest quarter, compared with a year-ago loss of $23 million, or 19 cents a share. Revenue dropped 36% from a year ago to $2.31 billion, as house-sale closings dropped 33% from a year ago and prices tumbled 15%. The stark numbers left CEO Tim Eller pointing to lower inventories, a big land sale (made at a $395 million loss) and some debt reduction as the quarter’s main accomplishments.

“We were disappointed with our lack of operating earnings, but believe these actions position us to continue to build an even stronger cash position and to restore operational profitability in the future,” Eller said. “Notwithstanding the outlook for a weak housing market, we are committed to delivering quality homes for our customers and to building a better Centex.”

Problems in the housing market, where inventories remain elevated despite a sharp drop in prices over the past year, have been a significant factor in the Fed’s decision to cut interest rates by 3.25 percentage points since September. And though the Fed signaled Wednesday that it will remain vigilant about fighting inflation, suggesting a pause in the rate-cutting campaign, observers such as Westwood Capital managing director Len Blum are projecting more cuts by year-end, as the economy continues to struggle along. He doesn’t expect to see investors return in numbers to the debt markets until house prices fall in line with rental rates. That could mean a further house-price decline of at least 10%, he says - which would be more bad news for capital-strained banks, and for housebuilders like Centex.

Private-equity firm TPG is looking to play a bigger role in the financial sector. The firm, which earlier this month led a group that invested $7 billion in Washington Mutual (WM), has been discussing closer ties with Merrill Lynch (MER), the Financial Times reports. Merrill chief John Thain has said Merrill doesn’t need new capital, but TPG is “hoping to get the first call” if that changes, the FT reports. Merrill has also talked with TPG and others about being co-investors in the firm’s private-equity ventures, The Wall Street Journal reports.

TPG isn’t limiting its discussions to Merrill, however. Reuters reports that the private equity firm, run by David Bonderman, has held a number of discussions with other financial institutions in recent months as it seeks to put $20 billion in “dry powder” to work. TPG was among the buyers of $12 billion of leveraged loans from Citi (C) last week, Reuters reports. It adds that TPG “aims to position itself as one willing and able to put up capital for minority stakes in financial institutions” as firms tally up the damage from the credit crunch. With Goldman Sachs analysts predicting this week that Ambac (ABK) and MBIA (MBI) alone will need to raise $3.4 billion each, it seems clear that there will be plenty of opportunity for firms like TPG to make their mark.