Throughout his oeuvre, Jonathan Sacks teaches that Judaism rejected the idea of the so-called “unencumbered self,” a conception of selfhood that he believed was a symbol of modernity and had become deeply entrenched in the type of liberalism presented most influentially in the work of John Rawls. Instead, Sacks argued, Judaism presents us with the view of personhood found in communitarian responses to Rawls, whereby we are essentially situated, with our identities tied to the “encumbrances” that define us. Yet it appears that an argument could be constructed to show that what Sacks sees as a “modern misconception of selfhood” played a key role in his own response to issues surrounding Jewish denominationalism, which formed the focus of his 1993 work One People. Through the lens of this example, this paper will examine the extent to which his attempt to navigate the rocky road between academic philosophy and community-facing theology results in a more general fissure in his thought.