In 1999, Jack succesfully launched his first mayoral campaign. Jack thrilled the crowds and won the hearts and minds of the citizens of Brookside...

This is the text of his stump speech (though he frequently would digress and offer ad lib remarks.)

Ladies and gentlemen, boys and ghouls, I wish you a Happy Halloween! What a beautiful day! What a wonderful parade! What terrific costumes! From the pumpkin patches of Bixby to the haunted mansions of Maple Ridge, may this Halloween be filled with the happy memories of times past, and filled with the magic of all the future may hold! I wish you the will to seize the happiness of today, for it shall pass quickly. The harvest will be over, the leaves shall fall, and winter will be upon us. So I say to you, Happy Halloween!

As you may know, I have petitioned to be your humble servant, the Mayor of Brookside. If elected, I cannot promise a perfect Halloween, but I can promise a better Halloweeen. I ask you: Do you have enough candy yet? Are there enough haunted houses in your neighborhood? No, to all! A vote for Jack is a vote for more candy, more haunted houses, and the return of the happier spirits of this magical season!

If elected, I promise full-size candy bars, a jackolantern on every porch, and safe streets full of happy children! I promise bountiful pumpkin patches, and the return of the happier spirits of yesterday! These are not the sole wishes of one dreamer, but the shared hopes of all who cherish the simple joys of a kinder, gentler halloween.

Thank you for your support! Thank you for dressing up so wonderfully for this happy occasion and for keeping the magic alive! Happy Halloween!