BEND, Ore. (KTVZ) — The family of a Troutdale couple and their two teenage children, killed in a devastating 2023 crash on Highway 97 north of Redmond, has filed a $50 million wrongful death and negligence lawsuit against the driver, his employer, and their insurance company. The suit seeks accountability for what they describe as a preventable tragedy that destroyed four lives and left an enduring void in their community.
A Tragic Day on Highway 97
The crash occurred in October 2023 as Gary Rutledge, 57; Michelle Rutledge, 53; and their children, Ryan, 17, and Kate, 15 — both students at Reynolds High School — were driving to Central Oregon to watch an annular eclipse. Their SUV was struck head-on by a pickup driven by Jesse Carl Ross, 44, a wetlands engineer employed by Ducks Unlimited.
According to court documents, Ross crossed the center line while driving under the influence of cocaine, caffeine pills, and severe sleep deprivation. The impact caused the Rutledge family’s SUV to burst into flames, killing all four occupants instantly.
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Driver Sentenced to 24 Years
Ross was sentenced in January 2025 to 24 years in prison after pleading guilty to manslaughter, DUII, and criminally negligent homicide. He initially pleaded not guilty to seven charges before reaching a plea agreement.
At his emotional sentencing hearing, Ross expressed remorse to the victims’ family and friends. “I would gladly trade places with them in an instant,” he said tearfully.
Ross had been on a 13-hour drive home from a work meeting in Klamath Falls that he was required to attend by Ducks Unlimited. Investigators determined he had been awake for most of the previous night, having slept only two hours before getting behind the wheel.
Allegations Against Ducks Unlimited and USAA
The wrongful death lawsuit, filed in Multnomah County Circuit Court by representatives of the Rutledge estate, names Ross, Ducks Unlimited, and the family’s insurance provider, USAA, as defendants.
The suit alleges that Ducks Unlimited bore responsibility for the tragedy because it required Ross to cover his own travel costs, leading him to drive instead of fly. It also claims that Ross exhibited “erratic” behavior at the meeting, which should have alerted his coworkers and supervisors that he was unsafe to drive.
According to the complaint, Ross had previously shown signs of substance abuse and performance issues. Despite this, the nonprofit “took no further action” to ensure his fitness for duty or his safety on the road.
The Rutledge family’s attorney, Jon D. Friedman, argues that the organization’s failure to act directly contributed to the deadly crash.
USAA, the Rutledge family’s insurer, is also named in the lawsuit. The plaintiffs allege the company breached its obligations by failing to pay underinsured motorist benefits as required by their policy, despite the family’s catastrophic losses.
A Family’s Grief and Their Fight for Accountability
In a joint statement shared through their attorney, surviving family members Allen Rutledge (Gary’s brother) and Linda Windsor (Michelle’s mother) described the lasting pain of their loss:
“As our family continues to struggle with the unspeakable loss of my daughter, and our brother, and their beautiful family, we are haunted by the milestone of their preventable and horrific death. Not a day goes by that we don’t mourn their tragic passing or miss their irreplaceable presence. An entire limb of our family tree has been cut off, and that impact will be with us forever. The Troutdale community lost four shining stars who brought light and love to everyone they met.”
Attorney Jon D. Friedman echoed their grief and called for systemic accountability:
“What happened to Gary, Michelle, Ryan, and Katherine is beyond a tragedy. No family should ever have to experience what the Rutledge family has endured. When organizations like Ducks Unlimited prioritize business interests over public safety, innocent people suffer. Mr. Ross and Ducks Unlimited are clearly responsible for this horrific event and must be held accountable. Our ultimate goal is to prevent future tragedies like this from happening to any other Oregon family.”
A Preventable Tragedy
Court documents detail how Ross’s exhaustion and drug use culminated in a deadly sequence of events. On that fateful morning, he drifted across the center line of Highway 97, sideswiped a semi-truck, and collided head-on with the Rutledges’ SUV. The collision instantly engulfed both vehicles in flames.
Investigators later confirmed that Ross had consumed Xanax, cocaine, and caffeine pills, and had barely slept before starting the long drive from Klamath Falls. Witnesses at his meeting earlier that day reported his “unsteady” demeanor and noted signs of extreme fatigue.
Community and Legal Reactions
The tragedy devastated Troutdale, where the Rutledge family was active in their church, school, and community events. Memorials and vigils were held in their honor, with hundreds of residents mourning the loss of what many described as “a family that radiated warmth, laughter, and generosity.”
The lawsuit represents more than a quest for monetary compensation — it seeks justice and reform. Friedman’s firm hopes the case will pressure organizations to implement stronger safeguards for employee travel and fatigue management, especially when workers are required to undertake long drives.
As of now, Ducks Unlimited and USAA have not issued public responses to the lawsuit. Both have been contacted for comment by KTVZ News.
Looking Ahead
The $50 million lawsuit aims to ensure accountability for the Rutledge family’s deaths while shining a light on the dangers of workplace negligence and impaired driving. For the surviving relatives, the legal action is also a way to preserve the memory of four loved ones whose lives were taken too soon.
Though no court ruling can undo the tragedy, the family’s attorney hopes the case will lead to policies that prioritize human safety over corporate convenience.
As Friedman stated, “The Rutledge family’s loss is immeasurable. Their hope is that this case serves as a wake-up call — one that prevents another Oregon family from suffering the same heartbreak.”
