Annie Olup was driving to Virginia Beach for her birthday weekend when her car flipped on a rain-soaked stretch of I-95. Strangers pulled her out through a window. But her two goldendoodles, Tobey and Bailey, were in the back seat, and in the chaos, both dogs vanished.
What followed was a search that lasted more than two weeks and brought together a worried family, a retired state trooper, a drone pilot and a volunteer “dog trapper” who refused to give up.
A Rollover Crash on I-95
Annie, 66, was heading south from King George to celebrate her birthday with family, her son-in-law Edward Quinones-Doyle told 12 On Your Side (WWBT) in Richmond. It started to pour. Back at the family’s home, they got a location alert that something was wrong, and Annie didn’t answer her phone.
Near the Kings Dominion exit in Caroline County, Annie’s car was caught up in a multi-vehicle crash. “[She] hit the guardrail bumper and basically flipped, you know, to the left several times,” Quinones-Doyle said. The car landed upside down and backwards, facing opposite traffic.
Nearby drivers stopped and pulled her to safety through a window. She was taken to VCU Medical Center, and she was hurt far worse than the family first heard. Annie ended up in the ICU with fractures to her sternum and spine.
Those dogs meant everything to her. Annie lost her husband in August 2024, and caring for Tobey and Bailey had become her purpose, CBS News reported. “I thought, I’m going to go back to this house and it’s just going to feel so empty,” she said of losing him.
Two Dogs, Two Different Escapes
“So Tobey got spooked and ran into the woods. And Bailey stayed at the accident,” Quinones-Doyle said.
Caroline County Animal Control took Bailey in. But she was desperate to find her owner. “Jumped the fence and she was gone into the woods,” he said.
Now both dogs were loose in unfamiliar territory, and Tobey had been reported running through the busy southbound lanes of I-95 near the crash site.
With Annie in the ICU, Quinones-Doyle knew she would be heartbroken if her dogs didn’t come home. “So I’m thinking to make myself useful, you know, maybe I can try to see what I can do about rescuing these two dogs,” he said.
He turned to social media for help. A retired state trooper saw the plea and connected him with Christine Quaiff of Trap Em RVA.
The Volunteer Who Wouldn’t Quit
Quaiff describes herself as a “computer nerd by day, dog trapper by night.” By day she works as a senior technical account manager in software development, according to CBS News. She often heads deep into the woods around Richmond to track lost dogs, and she has found dozens of them over the last few years. She’s part of a growing national network of lost pet recovery specialists who offer this service, often for free.
“When someone loses their dog, that’s their child,” she told CBS News.
She was deeply worried about Tobey. “I knew that Tobey was going to be staying near that accident site, as most dogs involved in accidents do. That was my biggest concern: how is he going to survive that?” she told 12 On Your Side.
She set up cameras and a feeding station near the crash site. Tobey showed up within a few hours. “He showed up to that camera within a few hours, hysterically crying. He wouldn’t eat,” Quaiff said.
She set traps, changed the food twice a day, and kept checking her cameras constantly. She even slept in her car in the search area, CBS News reported.
Drones in the Dark
The search area was hard to reach. It couldn’t be accessed by vehicle and wasn’t built to be walked on foot.
On day three, James Sullivan of Spearhead Drone Services joined the effort. “We use thermal imaging cameras that are mounted to drones, and we’re able to – we can see deeper into the woods than what a typical person is walking can do,” he said.
Even with that technology, it wasn’t easy. On the first night, the team could hear barking, but every time they got close, the scared dog kept moving.
Writing about the case, lost pet expert Kat Albrecht shared Trap Em RVA’s own account of what it took: “Cameras, feeding stations, drones, traps, long hours, sleepless nights and a whole lot of teamwork.”
After about ten days of searching through sun and rain, Tobey was finally caught near the crash site. He had lost 20 pounds in the wild.
Then the team turned to Bailey. Cameras and food did the trick again, and five days after Tobey, Bailey was rescued within a mile of the shelter she had escaped from. In all, she had been missing for 16 days.
Home Together Again
When Annie saw her dogs again, the tears came right away, CBS News reported. The three of them are now home together.
Annie is out of the hospital and slowly recovering. Her family has been through so much loss in the last few years, and 12 On Your Side described the reunion as a miracle they are cherishing.
“This was probably the most collaborative effort that I’ve ever seen,” Quaiff said, giving a big share of the credit to the family members who showed up every single day. There was also the retired trooper, help from VDOT, and Sullivan’s drone.
Quinones-Doyle later brought everyone who helped together to meet Annie and say thank you, and he nominated Quaiff for 12 On Your Side’s Acts of Kindness Award. She won.
For her, the reason is simple. “It’s about being kind to other people and doing what you wish people would do for you,” she said. “The joy of seeing them be reunited is ultimately what makes us keep going.”
If Tobey and Bailey’s story made you smile, share it. And give your own dog an extra hug tonight.