What did Oakland get after dismissing lawsuit against Southwest? Fewer flights

Last October, the Oakland City Council voted to drop a major lawsuit against Southwest Airlines. 

The City Attorney had accused the airline — the nation’s third largest — of depriving some of its 3,000 of its employees of paid sick leave and retaliating against some who tried to use their time-off benefits. The city settled similar allegations with Southwest in 2020, but new complaints about other violations prompted the City Attorney to restart litigation. 

The City Council didn’t provide a reason for dismissing the case. But two councilmembers who spoke with The Oaklandside said they had concerns with how long the legal battle was dragging on and how it might affect Southwest’s business. 

Southwest accounts for 80% of air traffic at Oakland’s airport, making it far and away the city’s most important carrier and a big source of revenue. 

Some city leaders hoped to strengthen Oakland’s relationship with Southwest after the lawsuit was dropped. 

Councilmember Ken Houston, whose district includes the airport, told The Oaklandside last year that the council was signaling to other companies that Oakland wanted to make partnerships with businesses, and that he planned to “break bread” with Southwest representatives. 

Mayor Barbara Lee met with Southwest’s CEO days after the lawsuit was dropped to discuss partnerships to promote Oakland’s airport. 

So far, it’s unclear whether the city’s actions have helped Southwest or the airport. 

For the first eight months of 2026, Southwest saw a 13.5% decrease in scheduled flights through OAK compared to the same period in 2025, according to data provided by OAK. Southwest also scheduled roughly 1 million fewer seats for passengers on its flights through Oakland during the first part of 2026 compared to the same period last year, dropping from about 6.5 million to 5.6 million – a nearly 15% decrease. Seats is a reflection of the number of seats the airline scheduled, not the actual number of passengers that flew, according to airport officials.

Flights for all airlines dropped precipitously at OAK during the COVID-19 pandemic. Despite a brief upswing in 2023 — and a protracted effort to change the airport’s name to make it more recognizable to travelers — traffic at OAK has not recovered to its pre-pandemic levels, and in fact has steadily declined since 2024. The recent decrease in passenger traffic at the airport roughly mirrors Southwest, which makes sense given the company’s overwhelming footprint at OAK. 

Oakland airport officials have blamed OAK’s passenger woes on the decline in business travel that started during the pandemic. However, Southwest representatives have boasted that business travel is strong in California, according to the San Francisco Business Times. 

We asked Lee’s office if Southwest has implemented any new strategies to boost passenger traffic at OAK. In an email, spokesperson Sarah Henry said the office is not aware of any. 

Henry added, “We are aware that there have been industry-wide issues with the high cost of travel and understand that Southwest remains as committed as ever to OAK.” 

Rising fuel costs have put financial pressure on various airlines. But Southwest has also reported significant profits as the airline shifts its business model. Locally, the company has added more flights to Oakland’s West Bay rival, SFO. The company recently relaunched a popular route from SFO to Burbank and plans to add an additional route to Kansas City later this year. 

The Oaklandside emailed Southwest questions about why the company is flying fewer flights through Oakland. 

“Oakland is a base city for our flight crews and an important part of our evolving network strategy – especially as it relates to intrastate travel in California, where we’ve been the market leader for many years,” the spokesperson said. 

They added that Southwest will offer up to 85 peak-day departures from OAK in December 2026 and February 2027, representing incremental month-over-month increases. 

The company representative refused to answer questions about their meetings with the mayor and councilmembers, claiming these were “privileged and not for public discussion.”

Mayor Lee was preparing to discuss lawsuit with Southwest before council suddenly dismissed it

When Mayor Lee met with Southwest’s CEO Robert Jordan — five days after the city dropped its lawsuit — the two leaders did not discuss the recently terminated litigation, according to Lee’s office. 

But before the council made its decision, some of Lee’s lieutenants anticipated the conversation with Jordan would touch on the legal fight – and that Southwest’s CEO would potentially ask for the mayor’s help getting rid of it. 

According to public records obtained by The Oaklandside, Lee’s deputy chief of staff Preston Kilgore and Visraant Iyer, director of her innovation team, prepared a “scene setter” memo for Lee for her conversation with Jordan. 

The memo describes the meeting as an opportunity for the mayor to introduce herself to Jordan. Lee’s staffers added that, “We expect Mr. Jordan to outline his position on the lawsuit the City has filed against Southwest Airlines, as well as ask for what you can do to resolve this lawsuit as soon as possible.” 

According to the memo, Oakland had requested $6 million to resolve the lawsuit against Southwest, which the airline refused to pay because it believed it had committed no wrongdoing. Southwest had “offered other concessions” to the city, but the memo doesn’t get into detail about what they were. 

Staff expected Jordan to raise a couple of other issues, including challenges with retaining employees and safety concerns around the airport. According to the memo, Southwest had advised its own flight attendants and pilots to stay in their hotels when staying overnight in the city.

The memo says that Southwest had also “reduced flights out of Oakland by 20%. At the same time, flights have increased out of San Francisco, and remained flat out of San Jose.” 

The 20% figure comes from an email that OAK’s chief public engagement officer Matthew Davis sent to the mayor’s office a couple of weeks before Lee’s meeting with Southwest. 

Davis’ email included data from Southwest showing the year-over-year increase and decrease in the number of flights the airline scheduled month-to-month between November 2025 and June 2026. The table compared OAK to San Francisco, San Jose, and Santa Rosa. Davis’ data shows that Oakland would be shedding hundreds of Southwest flights every month, while SF gained hundreds. 

“This is pretty unprecedented in my immediate recollection,” Davis wrote in his email. “[It’s also] reflective of every conversation we’ve had with them in the past two years about the ongoing litigation as they look to manage their fleet deployment and growth opportunities at various airports in the region.” 

For several weeks leading up to the meeting, mayoral staffers were in communication with Ruben Zaragoza, a lobbyist for Southwest. According to public records, staff in Lee’s office appear to have had a couple of conversations with Zaragoza before the meeting, but it’s unclear what they discussed. Zaragoza did not respond to an interview request.  

Mayoral spokesperson Sarah Henry told The Oaklandside that the lawsuit was not brought up as a potential discussion point. She said the mayor’s conversation with Southwest’s CEO was to discuss opportunities for the city to partner with the airline, especially regarding workforce retention and recruitment. 

“In addition to talking about staffing, they discussed Southwest’s commitment to being in Oakland and expressed interest in attending community events,” Henry wrote. The discussion about public safety was centered around how efforts to reduce crime would help with Southwest’s workforce issues, she added. 

“There were not any specific asks or offerings,” Henry added. 

Southwest did not respond to questions about some of the issues described in the memo. 

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