‘Nighttime Nailer’ Sentenced to 30 Days in Jail for Dumping Nails on Oregon City Roads

The man known as the Nighttime Nailer and the Nail Bandit, who admitted to dumping large quantities of roofing nails on busy Oregon City roads on dozens of occasions, was sentenced this week to 30 days in jail.

Bret Michael Wilson, 57, of Oregon City, had previously pleaded guilty to one count of second-degree criminal mischief and four counts of second-degree disorderly conduct, and on Tuesday, he was sentenced before Clackamas County Circuit Judge Susie Norby.

Deputy District Attorney Bryan Brock said Wilson was also given 24 months of bench probation, meaning his behavior will be monitored by Judge Norby herself rather than a probation officer, and he was ordered to pay restitution to nine victims in the amount of $2,251.09.

His crimes had impacted many more than that, but only nine said they wanted restitution, and had also filed a police report and could provide documented proof of damages.

“There were many more victims, but many of them were not seeking restitution for a variety of reasons,” Brock said, such as the amount of the damages being too small (in some cases, local shops had even fixed the damaged tires for free) and it not being worth the hassle.

Initially believed to have been active for about two years, Brock said Wilson claimed to have been scattering nails at various times for over a decade. He operated in the early morning hours, pre-dawn, typically on his way to work.

Brock said Wilson bought the roofing nails and the other materials he used in his crime spree at the Home Depot, and also at stores outside Oregon City, so “as to avoid being caught buying large amounts of nails.”

According to his own testimony, he went through about three “large tubs” of roofing nails every “season,” which for him meant fall, winter and part of spring.

“He wouldn’t do it in the summer because it got too light too early,” Brock said. “His seasons were when it was dark enough not to be seen.”

Now, the big question: Why did he do it? Why did he wake up early, day after day, and drive the quiet streets of his own community, sprinkling nails and tacks with the expressed desire of popping his neighbors’ tires, seriously inconveniencing them — and, possibly much worse?

According to Brock, it was because he was angry.

Of course, after months and even years of his criminal behavior, Wilson wasn’t the only one who was angry. The Nighttime Nailer’s spree engendered fear, outrage and vitriol, and his sentence was not well-received by many. (Heck, for some online commenters, the death penalty would have been too lenient.)

As Brock explained, a 30-day jail sentence is actually an unusually stiff penalty for a misdemeanor conviction. That doesn’t change the most common thing we’ve heard since Wilson’s sentence was handed down: “Only 30 days??”

The judge handed down the more serious sentence, Brock said, because of the length and extent of Wilson’s behavior, and the impact it had on the community and the taxpayers, with the many hours spent by Oregon City police and maintenance workers investigating his crimes and cleaning up the aftermath.

Brock said that Wilson told police he would be willing to write a letter of apology to his victims, and admitted he hadn’t fully thought through his actions and who it might affect: emergency vehicles responding to a call, buses and parents carrying children to school, folks — like him — who were just trying to get to work on time.

On the other hand, when asked if Wilson expressed remorse or seemed to regret his actions, Brock wasn’t so sure.

Judge Norby also ordered Wilson to undergo a mental health evaluation, and to follow any course of treatment that is recommended. If he violates probation following his 30-day sentence, he could face up to an additional 11 months behind bars.

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