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Recent research in economic history has found that mortgage debt in relation to GDP has taken off in the historical long run (“great mortgaging”), as growing banking assets have been redirected into mortgage credit. This paper maps the parallel long-run investment history of private (life) insurance as the much overlooked second pillar of the financial system. Drawing on in-depth studies of the US and Germany, it finds that a “great de-mortgaging” took place in insurers’ portfolios, with mortgages falling from up to 90 percent in the 19th century to below 5 percent today in favor of fixed-income securities. A parallel shift to secondary mortgage bonds has hardly offset this decline, while direct real estate remained largely a residual investment class. Banks’ great mortgaging is thus partly an institutional substitution effect. The paper sees insurers’ asset shift itself as mainly driven by long-run changes in capital demand and competition with banks and pension funds. It extends these findings to other long-term institutional investors and other OECD countries in the historical long run.