The year is 2053, and land trusts everywhere are grappling with the legacy of conservation easements negotiated in 2023 when our grantor-landowners lived on ranches and farms that had been handed down through the generations. They trusted us to help them steward their lands and we counted on their support of our shared vision. In 2053, we now have a new generation of landowners who live in Los Angeles or New York City. They are smart, savvy, know their way around legal documents and are used to getting what they want. Their only exposure to conservation easements was a passing reference in some random streaming western called “Yellowstone.” The Rally Players will take you back in time to when the tax deductions flowed, the ranchers did business with a handshake and a promise and we could get away with vaguely worded conservation easements because we knew our landowner was “conservation-minded.” We’ll show you how, as people and conditions change, conservation easement language gets interpreted, misinterpreted, ignored and even litigated, to create unintended legacies for land trusts. If we knew then what we know now, could we set history/events/the future on a different path?