Oakland to pay bicyclist $7M in record pothole settlement

OAKLAND, Calif. - The city of Oakland is poised to pay a bicyclist a record $7 million after his wheel struck a pothole on Skyline Boulevard, causing him to be in a coma and suffer a long-term brain injury.

Record $7M pothole payout

The city agreed to settle with Ty Whitehead, 58, of San Francisco earlier this month and the city council is expected to formally approve the payout on Oct. 7. 

It is the largest such settlement Oakland has ever paid over a pothole.

"I just hope Oakland realizes that it's cheaper to repair the roads than to keep paying cyclists," Whitehead said in an interview on Tuesday. 

He was injured in March 2017, when he was training for an AIDS ride in the Oakland hills. His bike wheel hit a deep pothole on Skyline – a popular biking area and steep road – throwing him over his handlebars and onto the pavement. He was in a coma for two weeks and suffered brain damage and permanent disabilities. 

Whitehead left his job serving as an operations manager for two law firms and now, he said he needs to get help from his mother and sister to decipher dense material, like insurance forms.  

"I don't work anymore, and I have a hard time reading things that are kind of complex," he said. 

‘Grim honor’ 

Whitehead's settlement is higher than the $6.5-million settlement paid in 2023 to Bruno Van Schoote, who injured his spine while riding his bike over a crack in the road along MacArthur Boulevard, and another $6.5-million paid in January 2024 to Lynne McDonald, who crashed her bike riding over a pothole on Grizzly Peak Boulevard causing serious injury and paralysis. At the time, those two settlements had been Oakland's highest. 

Whitehead's attorneys from the Veen Firm in San Francisco also represented Van Schooote. 

"It's a grim honor to have the highest settlements against Oakland," said attorney Anthony Label. 

His colleague, attorney Steven Kronenberg, added: "It is very important to recognize that although a pothole might seem like a minor inconvenience to someone driving in a car or a truck, if you're on a bicycle, it's a very serious hazard with very serious life-altering consequences. If the city could try to fix the problem before this type of tragedy happens, that would benefit everybody."

Oakland has highest pothole payout

Whitehead's payout also brings Oakland's total pothole settlement total to roughly $34 million, from 2018 to present, an analysis of data from the city attorney's office shows. 

That's a far higher dollar amount than another other Bay Area city, a KTVU investigation found.

San Jose paid $8 million from 2018 to 2023, a review of city attorney data showed. San Francisco paid out $26 million in the same time period for all street maintenance lawsuits; the city doesn’t parse out what is owed for pothole damages. Both cities have about 1 million people and are roughly three times the size of Oakland. 

City of Oakland 

The city of Oakland had no comment regarding Whitehead's case. 

But days after KTVU published its investigation in July 2024 regarding Oakland's pothole payouts being the most of any Bay Area city, the city's Public Works crews jumped into action, specifically paving over Skyline Boulevard. 

At the time, Josh Rowan, Oakland director of Public Works and the Department of Transportation, said he felt awful about the injuries that the city’s potholes have caused.

"We certainly don’t want those injuries to take place," Rowan said last summer, calling some of the city’s potholes "catastrophic failures."

These failures were caused, Rowan said, by more than a half-century of not taking care of the roads.

Until recently, some streets in Oakland hadn’t been paved for 80 years. Winter rains just exacerbate the issue.

Oakland voters passed Measure KK in 2016, providing $350 million over a 10-year period to fix the roads. In 2022, voters also passed Measure U, which extends some of the paving funding.  

Rowan said that money allowed paving to begin in earnest seven years ago.

Since then, Rowan said 200 miles of road have been paved in Oakland.

He estimated that half the city will be paved in another four or five years at an estimated rate of filling 25,000 potholes a year.

Oakland will be fully re-paved in 17 years, Rowan estimated.

On Wednesday, Rowan said he wanted to remind Oakland residents that the city is looking to proactively repair frequent bike routes, and he has a team looking at 311 pothole submissions through the lens of risk to cyclists. 

California Supreme Court ruling

Part of the reason that it took so long for Whitehead's settlement to be approved is that the city of Oakland had argued it wasn't responsible because he had signed a liability waiver beforehand.

Alameda County Superior Court Judge Richard Seabolt and the state’s 1st District Court of Appeal ruled that the release required dismissal of Whitehead's suit. 

But on May 1, the California Supreme Court ruled in Whitehead's favor, writing that cities have a statutory duty to maintain public roads in a reasonably safe condition for all users. Justice Kelli Evans emphasized in the 7-0 decision that waivers cannot excuse a city’s legal obligations to ensure road safety.

"The Supreme Court made clear that cities and counties can't get out of their responsibility to maintain safe roads, they can't force people to sign releases to give up any right they have to seek compensation," Label said. 

Added Kronenberg: "It's important to recognize that the right of free travel on public roads is a fundamental right."

And that fundamental right is not just cars and trucks.

"It also applies to bicyclists, especially those like Ty Whitehead who were riding on a designated bike route in the city of Oakland," Kronenberg said. 

Life after pothole injury

Whitehead spends his days volunteering, taking walks and spending time with his mother and sister. He hasn't worked in 11 years. He gets by on Social Security and disability checks, and certainly doesn't ride a two-wheeled road bike anymore. 

He has tried out a three-wheel recumbent bicycle over the years, but "no freewheeling across Marin and the East Bay like I used to," Whitehead said. 

He misses the exercise, the stress relief and the camaraderie he got through bicycling. 

"It was a huge part of my social life," Whitehead said. "My accident ended a huge part of my life. My life completely changed in almost every way."