In its journey north, Polar Pioneer has temporarily docked in Elliot Bay, a move which O’Brien says is a "violation of the existing permits."
"We are working on enforcement actions to get them back in compliance," O’Brien says.
"Unfortunately, the remedy for us is to issue fines which escalate up to $500 a day, which for a company like Shell is really a meaningless amount of money…but it demonstrates their blatant disregard for local laws."
O’Brien has also taken to the water himself, joining the kayaking protesters in their efforts.
"For me, because it’s happening right here in my city, on my waterfront, I frankly can’t just stay in my chambers and work on this," O’Brien says. "I felt the need to get out there and join with my fellow citizens to be part of the activity on the water."
"The number of us and the size of us compared to this monstrosity is a monument to the hubris of the oil industry," he adds.