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How can the Constitution protect landowners from government exploitation without disabling the machinery that protects landowners from each other? The Supreme Court left this central question unanswered — and indeed unasked — in Koontz v. St. Johns River Water Management District. The Court’s exactions jurisprudence, set forth in Nollan v. California Coastal Commission, Dolan v. City of Tigard, and now Koontz, requires the government to satisfy demanding criteria for certain bargains — or proposed bargains — implicating the use of land. Yet because virtually every restriction, fee, or tax associated with the ownership or use of land can be cast as a bargain, the Court must find some way to hive off the domain of exactions from garden variety land use regulations. This it refused to do in Koontz, opting instead to reject boundary principles that it found normatively unstable. By beating back one form of exactions creep — the possibility that local governments will circumvent a too-narrowly drawn circle of heightened scrutiny — the Court left land use regulation vulnerable to the creeping expansion of heightened scrutiny under the auspices of its exactions jurisprudence. In this paper, we lay out this dilemma and suggest that it should lead the Court to rethink its exactions jurisprudence, and especially its grounding in the Takings Clause, rather than the Due Process Clause. The sort of skepticism about bargaining reflected in the Court’s exactions cases, we suggest, finds its most plausible roots in rule-of-law concerns implicated by land use dealmaking. With those concerns in mind, we consider alternatives that would attempt to reconcile the Court’s twin interests in reining in governmental power over property owners and in keeping the gears of ordinary land use regulation running in ways that protect the property interests of those owners.