Portland Mayor Charlie Hales leaves office Dec. 31 after just one term. But four years still provided WW with plenty of fodder for caricature. Here are a few of our favorites.

(Andrew Zubko)
(Andrew Zubko)

"Return of Chucky," Jan. 29, 2013
Hales inherited a $21 million budget gap when he took office in January 2013, and he launched immediate efforts to cut spending.

(Kenneth Huey)
(Kenneth Huey)

"Goofus and Gallant Go to City Hall," Nov. 5, 2013
After a year in office, questions arose whether Hales was a loafer or a leader, with observers criticizing his handling of homeless camps.

(WW Staff)
(WW Staff)

"Mayor Charlie Hales Declares Oct. 15 'Hip-Hop Day' in Portland," Sept. 30, 2015
Hales attempted to make peace between the Portland Police Bureau and rap artists by declaring "Hip-Hop Day" at City Hall. Our writer dubbed him "DJ Sad Eyez."

(Colin Andersen)
(Colin Andersen)

"Charlie Sails Away," Oct. 27, 2015
Hales surprised many with his decision to walk away from his re-election campaign after Ted Wheeler jumped into the race.

(Matt Schu)
(Matt Schu)

"Pay at the Last Window," April 27, 2016
In his last year in office, Hales stepped up his advocacy for fighting climate change. In 2016, he sought to ban the construction of additional drive-thrus in the central city.