What happens when a multi-million-dollar sponsorship campaign is built around an athlete who never makes the squad? Drawing on examples from football and Olympic history, this essay explores the legal and commercial risks of athlete endorsements, explaining why careful contract drafting often matters more than what happens on the pitch.

A pair of 18th-century highway robbers went to court over an unfair split of stolen loot and accidentally helped shape one of the most enduring principles in contract law. In this first #casefiles entry, Mide Alabi revisits Everet v. Williams (1725), the bizarre English case that established why courts refuse to enforce illegal agreements and why that principle still matters today.