This is a 'will-in-context' study of a Toronto bequest of the 1880s that shows how a testator's ideological commitment to freedom of willing and his retention of high-powered legal talent to actualize that commitment were derailed by a hapless or avaricious executor, unpredictable real-estate markets, a lethargic court, and eccentric beneficiaries. It also suggests that self-made private law like contracts, trusts, and wills may be as doctrinally, textually, or administratively contradictory, indeterminate, or unpredictable as state-made public or regulatory law has often been shown to be.