In the meantime the few professional athletes have decided that Winchester is too small to support any kind of major sports team, and the few remaining athletes have now switched jobs.
Colleen Mendez, the last remaining athlete in town, is in Law Enforcement now, and Ernest Thao, who was the local Sports Agent, has gone into Politics. He had so much charisma skill that it wasn't hard for him to make the switch.
Other Sims have left their professions for rabbithole careers as well, but there is still a bit of a shortage.
* * *
In the meantime the Mendez family lost their oldest horse, Belladonna.
(Not sure why Grim is thinking of business deals and earning Simoleons here - perhaps he gets commission on every soul collected?)