How did this happen? Did anyone see it coming? With the arrest of one member of the Class of 2008 Friday morning in connection with “Paint Night” (more like “Paint Week”) vandalism, and word of more arrests on the way, we are left to wonder what made this specific group cross over the line that had been loosely drawn by previous practitioners of this long island tradition. Why them? Why now? Now what?

One could surmise that the paint splattering and tire slitting of police cars was a retaliatory response after officers stopped some kids from painting more than an island road. That makes sense since the damage to the cars parked at the police station and at the home of Police Chief Matt Haney was more about desecration than proudly making one’s mark on a road. These were acts of anger and the penalty, if the kids are caught or turn themselves in, could be more than a slap on the wrist. Embarrassing the chief of police and the city he represents is definitely a mistake. Plus, the quantity and span of this year’s vandalism may be unsurpassed.

Some estimate the tradition to be about 70 years old and islanders such as Neal Nunamaker, who spent 30 years here as a teacher, principal and superintendent before retiring in 1981, and Ralph Munro, a road painter himself as a member of the Class of 1961 and a former Secretary of State, have benignly watched it continue over the years. Both characterized the painting by seniors as nothing to get excited about because nobody got hurt. However, there have been some memorable flare ups over the years.

In the early 1950s, Nunamaker said, there was a slight uproar when seniors painted their class number on the side of a large ship anchored in Eagle Harbor. And Munro said two boys were arrested and jailed by Kitsap County Sheriff’s deputies about 20 years ago “when someone complained about paint splashing on their Mercedes.” Secretary of State Munro talked to the sheriff and prosecutor, telling them he would sit with the boys if they went to trial for misuse of paint. He never heard about it again.

Supt. Nunamaker had similar feelings about the tradition, but he objected to the kids climbing up the 135-foot-high steel water tower on district property. He feared for their lives and had a 15-foot-high fence placed around the tower’s base with a sign that said, “Survivors will be prosecuted.” None ever were, of course, including Munro, who said he climbed the tower (dismantled in 1995) five times. Nunamaker remembers informing police, however, when kids painted school bricks because of the expense of cleaning them. No one was held accountable, he said.

“In my day, most people took it as the thing to do, or as least that they’re only kids so why get upset,” Nunamaker said. “I don’t think kids have changed all that much, but they sure got carried away this year. When it comes to tearing up police cars, well, it’s not just kids having fun anymore. It sounds like somebody got their feelings hurt and they lashed out.”

While it appears cops and some kids are at war right now, Munro suggested they sit down, share a dialog and come up with some parameters that will allow the tradition to continue without recrimination. Like most of us, he doesn’t know what happened to cause the blow up, but he’d like cooler heads to prevail. “I don’t think there’s any great harm to painting the streets… the paint’s gone in a few months,” he said. “Let the kids feel proud about their accomplishment by putting their names on the street. There’s no harm.”

Well, the large amount of harm caused this June might have been severe enough to end a tradition many have savored. Times have changed, and there’s a good chance that some teenagers are going to pay a heavy price – as deterrents – for not knowing the accepted parameters of “Paint Night.”

Whatever they are.