If I were Goose and I thought I was a better player than someone else, I would simply do a one way bet. If Goose doesn't keep a lead over Jimbo by the end if the year, then Goose gives Jimbo $xxx for his accomplishment. If Goose maintains the lead, then he truly is superior and no money needs to be exchanged.
Additionally, you worded this bet horribly. One minute prior to noon, Jimbo could change all of his times to beat yours and pass you on the ranks as noon strikes. He gets $5000 from you and a small timeframe ban from the ranks.