First step: Who writes them?
Start your outreach by noting who writes columns and publishes cartoons in your newspaper over a two- or three-week period. Note when they write and what they write about. Also, look at the byline to see how the writer or cartoonist is described.
Second step: Note where the cartoons and columns come from.
Once you've done that, review your notes. Scratch from your list any columnists or cartoonists whose work comes from a syndication service, like King Features or Creative Syndicate. They write for a national audience and your local message isn't likely to make it into their columns. Also scratch from your list columnists and cartoonists whose work is always and entirely about national issues. They, too, are unlikely prospects. Check the cartoonists' signatures, usually in the cartoon itself, and see if they are syndicated or work for out-of-town newspaper. If the cartoonist is local, keep them on your list; if not, do not waste your time.
Third step: Target those locally that could be interested.
What's left on your list should be local columnists and cartoonists whose work is about local issues. Next, set priorities by seeing who has shown interest in education issues, or in children, juvenile crime, and so on. Then try to get a gauge on their likely views on the issues to see if they are likely to be supportive.
Fourth step: Let them know how important afterschool is.
Next, write or call the columnist or cartoonist to let them know about the problems afterschool programs are having finding startup funding in the community, for example. If you write, send backup materials. If you call, be prepared to answer questions and to send follow-up material supporting your message. Also, be sure to let them know if there's a significant date coming up—graduation time, back-to-school, or a local Lights On Afterschool event—so that they'll know that anything they write would have the most impact around that time. If you say you'll send additional materials, or promise anything else, be sure to act quickly before the memory of your conversation fades.
Fifth step: Step back, but follow up if something significant happens.
Then give them some time to take in the information you've sent and publish, if they choose to, when they see fit. After a few weeks, if something significant happens that you think they'd want to know, drop them a note, send them an email, or give them a call.