Within the next 14 days:

• An offer to bondholders to restructure about a tenth of the company's $20 billion debt load expires Thursday. Delta officials and outside experts have said the carrier's ability to restructure its debt is key to avoiding bankruptcy.

• The leadership of its pilot union meets this week in Florida. Talks have resumed between management and the pilots over the $1 billion in annual cost cuts the company is seeking. Those negotiations could expand and accelerate as a result of the meeting, or the union could decide to take a different tack.

• The airline releases its third-quarter results Oct. 20, which will show how much cash it still has on hand.

"The next couple of weeks clearly are a crucial period in trying to avoid bankruptcy for Delta," said Phil Baggaley, senior airline credit analyst with Standard & Poor's.

If resolutions to the debt and pilot issues "are not in place in a matter of weeks, our airline will be required to restructure through the courts," Delta senior vice president and chief of operations Joe Kolshak said Monday in a speech in Atlanta.

The company's release of third-quarter earnings also could give executives a chance to provide some guidance on a possible deadline for settling both the pilot and debt issues.

Delta has lost more than $5.5 billion in the last three years, and Wall Street estimates call for a loss of nearly $3.58 a share in the third quarter, or a total of about $450 million. That does not include a possible charge for a large number of early pilot retirements.

Delta has not yet set a deadline for a deal with its debt holders or its the pilots, but some experts say they need to act soon, although the company's "cash burn" was expected to slow in the busy summer months covered by the third quarter.

Delta already has depleted its cash reserves - it was down to just over $2 billion in cash and short-term assets at the end of the second quarter. Experts have said if that figure drops below $1.5 billion, bankruptcy is inevitable.

'Tip of the iceberg'

To help stem the outflow of cash, Delta offered $680 million to the owners of about $2.6 billion worth of the company's secured debt on some older airplanes.

That's about 26 cents on the dollar. Holders of debt of United Airlines and US Airways have received or are expected to get just 2 cents to 3 cents on the dollar as the bankruptcies at those carriers progress, but that was for unsecured debt.

"The owners of (Delta's) secured debt may want to take their chances in court," said Bill Warlick, senior airline debt analyst at Fitch Ratings.

Delta has set a deadline of Thursday for its bondholders to respond, and in an unusual move, the company is asking for a 90 percent approval rate.

"Typically, the company asking for a debt restructuring extends the offer and doesn't ask for that much approval," said Rich Bittenbender, senior vice president for Moody's Investors' Service. "But this is anything but a typical situation."

The company would not comment on the offer or on any other financial issues, saying it is in a "quiet" period before its earnings release.

Bittenbender said if the vote is not extended, it could be a sign of what is happening with other debt holders, including those who hold both secured and unsecured debt.

"This is the tip of the iceberg," Bittenbender said.

In fact, Delta is in negotiations with holders of at least 25 percent of its debt, Delta chief executive officer Jerry Grinstein said Sept. 8, the day the airline unveiled its restructuring plan. But he added that it has been hard to tell who is representing which debt holders, if those representatives actually are working with real debt holders at all.

"Just getting the list of the debt holders is a tough enough task, since this stuff is bought and sold daily," Bittenbender said. "Then you have to talk with all of them, which turns into a real snake pit."

Hank Shafran of the law firm Bingham McCutchen would not say how much debt is included in the group he represents, the Committee of Senior Secured Aircraft Creditors of Delta Air Lines. But he did say the committee has been unimpressed with the information Delta has passed out so far.

Pressure on pilots

Bittenbender also said the company could use an approval of the debt exchange to put more pressure on its nearly 8,000-member pilot union, which includes nearly 800 based at the hub at the Cincinnati/Northern Kentucky International Airport.

The two sides have been talking about givebacks for nearly 15 months. The airline's pilots are the highest-paid in the industry, and the union has offered up to $705 million worth of annual concessions. But the company has not budged off its $1 billion figure.

Union spokeswoman Karen Miller said she saw no correlation between the debt issue and the pilot talks. "We have already said we need to contribute to this. Nothing from the outside is going to put any more pressure on the situation."

The union has a major meeting in Florida this week, which comes as the two sides have resumed talks over work rules. Miller said last week that the union was hoping to expand the talks to include an overall package that would include pay and benefits.

Last month, the union approved a side agreement by a 90 percent margin that allows the company to rehire recently retired pilots on key aircraft types to keep from having to cancel lucrative long-haul flights. More pilots than normal have been taking early retirements for fear that they will lose their pensions.

But in return for the rehiring power, the company pledged not to touch the pilot pension plan until at least February, even if Delta declares bankruptcy before then.

E-mail jpilcher@enquirer.com