Research into Hebrews’ use of the Jewish Scriptures is a long-standing discipline, and one which is commonly focused around the epistle’s appeal to key characters such as Moses, Abraham or Melchizedeck. A primary figure in this retinue is Joshua; consideration of how Hebrews links him with Jesus is particularly invited by the epistle, partly because of the common name, partly because of the tantalising reference of 4:8, partly because of the deafening silence of 11:29-30, and partly because the mantle assumed by Jesus bears such a strong resemblance to that bequeathed to Joshua upon entry into the land. The association, however, only works up to a point; the Joshua typology sits well with the hortatory aspects of the letter, but less easily with its doctrinal portions. To put it another way, Joshua imagery works well for Jesus’ archegos role, but is less compelling in its insights for his archiereus function. This paper will explore this other high-priestly aspect, and tease out whether Hebrews has a similar OT prototype in mind for the role, beyond the obvious affinity with Melchizedeck. In particular, it will examine the suitability of Caleb for this function; as the one who shares, with Joshua, a leadership role upon entry into the land, to what extent does Caleb inform Hebrews’ portrayal of Jesus? To what extent does Caleb complement, shape or supplement the Joshua typology, and can one even talk profitably about a Caleb typology? As such, the paper will explore the Caleb tradition in more depth, particularly the extent to which he may be said to bear a priestly – or high-priestly? – mantle. Is he indeed one who ultimately deals with “things pertaining to God” (Heb 5:1; cf. 2:17)?