Named for Miss Gay Portland XVII Eva Destruction who also served as Miss Sweetheart III, Eva Destruction was known for her enthusiasm and creativity. Killed in a tragic motor vehicle accident in 2007, this award was initiated that year and is to be given to one individual each year. The recipient is named jointly by the reigning Portland’s and is given at the Portland Pageant.
| Year | Recipient |
|---|---|
| 2008 | |
| 2009 | |
| 2010 | |
| 2011 | |
| 2012 | |
| 2013 | |
| 2014 | |
| 2015 | |
| 2016 | |
| 2017 | Sugarpill A. Valentine |
| 2018 | Sofia Valdez |