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I've not handled any campaigns, I've just watched a few from the outside. Hopefully you're sending constant press releases to all appropriate media, including small press freebie mags if you have any (we have a popular weekly here called the "Austin Chronicle" which loves local politics as well as entertainment news). The press releases should include any worthwhile endorsements you've gotten, any good polling info, any new speeches or campaign materials you have. It should list any upcoming events, and summarize previous ones. Don't give them so much they get annoyed with it, just highlight positives, like increasing crowd sizes or celebrity endorsements. And don't use a lot of adjectives and adverbs--they'll get bored with the hype. The media may not publish anything you send them, but they will file it away, and will consider it when they are doing stories on the election. Give them enough good stuff, and you may get a line like "Surprisingly strong candidate X is providing a real challenge to the incumbent."
Gimmics like faux awards only work if you've got some event surrounding it to give it credibility. If the incumbent has a spotty environmental record, for instance, get an environmental group to hold a rally at the site offended by some controversial legislation. If they have hurt retirement homes, give rallies at retirement homes. If they have focused on big issues and ignored their local communities, get to know neighborhood associations, and try to hold rallies (or better, get someone else to plan one) with local naighborhood groups. Make the event as large as you can, and hand out the award (or better, get the group to do it). Make the award funny and appropriate--a miniature chemical waste barrel with a skull and bones warning on it, or a collage of garbage with sludge dripping from it, or just the corporate emblem of the company your opponent has favored. The award isn't as important as the rally. The media is used to gimmics, and they won't report them just because they are clever. They have to show something--the strength of your challenge, your momentum, or some serious allegation involving fraud or a very questionable pattern of supporting large donors. It has to be news. Just being clever and pointing out the obvious isn't really interesting. It has to have some significance. But making it fun and anchoring it to a funny image , with pictures, helps people to remember it, and gives the story a sense of immediacy, as opposed to jst being a fact they can work into a story later.
The media is besieged by candidates wanting them to make their careers, so they really are adverse to that. On top of that, they want to build a good relationship with the incumbent (who also wants one with them), so they won't offend him/her by seeming to favor the challenger. You have to create a story for them to cover. The best way to do that is to campaign very hard. Knock on a lot of doors, and give a press release about how hard you worked (make someone write it third person for you). Visit all the local Dem clubs, and join the ones you are eligible to join (in my town, these clubs make or break candidates). Be tireless, and report how tireless you are. Try to get invited to any event you can, and make some up if you can't. The more the media sees you working and gaining votes, the more they will look for stories to work you into the news.
If you really want to win, and want to go negative, go really negative. A friend of mine was just beaten by a challenger who convinced the liberals her opponent was too conservative and the conservatives her opponent was too liberal. She had the police attacking her opponent for rejecting pay raises, and tax groups attacking her for supporting a toll road. One special interest group put out flyers showing the opponent wearing a crown and holding lots of cash in her hands, because she had a reputation of being a bit arrogant in person. The challenger won. She made a lot of enemies, though, but she won. I wouldn't do that, but some do. IF this is a primary challenge, remember that you have to win your own party, and if you are bashing someone else in your party, you are making enemies that may haunt you later.
You probably know all that already, but once I get typing I just can't stop!
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