The problem was that we didn't really have any money to do a whole lot about it.
I don't know if you've ever tried to pave 60 miles of roads and fix a bunch of potholes but it's not easy.
Then one day, my colleague, Commissioner Steve Novick bounded into my office all smiles.
"Mr. Mayor!" he exclaimed. "I've got the answer to our problems!"
He had my attention.
"I think we both agree that we need to leave no stone unturned in our efforts to find money for our transportation infrastructure," he said.
"So, let's write a letter to Santa Claus asking for money for transportation. We'll make the case why Portland deserves a stocking full of street maintenance, sidewalks and safety features on Christmas Day."
To this day, I remember his smile seemed to fill the room.
"We need to show that we are willing to go to the North Pole in the search for more transportation investments," he said.
Now, I have to admit that I was a little skeptical at first. After all, who had ever heard of a city trying to solve its fiscal problems by writing a letter to Santa?
But it occurred to me maybe no one had done it because they just hadn't thought of it.
So, we gave it a go and wrote the letter. We made the case.
And we waited.
On Christmas morning, I woke up bright and early, having been barely able to sleep the night before. I met Commissioner Novick at City Hall and beneath the city's Christmas Tree was a large box - a refrigerator could have easily fit inside - wrapped ever so beautifully.
I looked at Novick and he looked at me and we both shrugged our shoulders.
We tore at the paper like little kids until we got the box open. It was filled with $100 bills. We just kept diving through the cash, making sure there were no bills smaller. It was millions of dollars in cash. And a note.
"Dear Portland, got your letter and checked the naughty/nice list. The whole thing with the police and the mentally ill had originally put you on the naughty side by the elf auditors decided that the efforts you're making put you back on the nice side. Make sure to use the money for transportation projects or it will be lumps of coal next year."
And it was signed Santa.
Things really picked up after that.
We got in touch with the Easter Bunny that spring to see if he could help up with composting. The thought was that he was already going house to house so maybe it wouldn't be a problem. As you all know, it was a huge success. One that got even better when Mr. Bunny sat down with Santa to improve logistics.
Then there was what was perhaps the biggest success of all - working with the Tooth Fairy to improve Cover Oregon.
While there had been some success with the program, we knew the Governor was frustrated. Our thought was what could be better than a medical expert with magical powers?
The turn around there was so quick and amazing no one was surprised when the Obama Administration called, asking for contact information for the Tooth Fairy.
Of course, you all know the rest of the stories - getting Jack from beanstalk fame to help develop the urban farming program, the three little pigs revamping the city's outdated building codes it was just one success after another.
I guess my point is that when it comes to looking for solution to seemingly overwhelmingly large problems - don't be afraid to dream. No solution is too crazy.