10 Months Into Job, Southwest’s CEO Bob Jordan Faces a Giant Crisis

In the last few days, union officials, pilots and flight attendants have complained to journalists and on social media that crew members have often had to wait hours to be assigned to their next flight or be directed to hotels where they could spend the night.

Customers have also expressed intense frustration with the airline, saying it had become impossible to get any information from the company. Some people have said they waited hours at baggage and ticket counters and gates to speak to Southwest agents. Others have tried and failed to get through to the company by phone or online.

Howard Tutt came to Chicago’s Midway airport on Wednesday to try to retrieve a bag his son had checked for a flight to California that was ultimately canceled. He said he had waited hours with other customers to speak to someone to no avail. Nearby, dozens of bags were waiting to be reunited with travelers outside Southwest’s baggage office and near its carousels.

“He had to leave in the middle of Christmas dinner because they told him the only flight he could get on was at 9 p.m. on the 25th,” Mr. Tutt, 61, said, referring to his son. “Then he got to the airport, checked his bags and was delayed for six hours before they canceled the flight.”

Mr. Tutt, a resident of Orland Park, Ill., said the family had tried a variety of approaches to locate the bag, which contains Christmas gifts for his son’s girlfriend and her family. “We’ve emailed, tried via chat message, and called but cannot reach anyone.”

Analysts said that, as cancellations piled up, Southwest found itself in a dire position in which it needed to almost start from scratch to rebuild. “You’ve lost control of what you expected the operation to be,” said Samuel Engel, a senior vice president and airline industry analyst at ICF, a consulting firm.

The question that will loom over the company for a long time is why Southwest’s system broke down while those of other large airlines held up relatively well. Analysts say Southwest’s point-to-point network, which is quite different from the hub-and-spoke system used by its peers, made it harder to restart operations.