This picture is the pendant to a portrait of the sitter's brother and predecessor, Frederick III (1463–1525), the Wise (MMA 46.179.1).
When John the Steadfast died in 1532, his son and successor, John Frederick the Magnanimous, apparently ordered a large number of pairs of portraits of his father and uncle. Cranach received payment in 1533 for sixty pairs of such portraits, undoubtedly mostly executed by members of his workshop. Friedländer and Rosenberg, in "Die Gemälde von Lucas Cranach," Berlin, 1932, p. 79 (rev. ed., "The Paintings of Lucas Cranach," Ithaca, 1978, pp. 135–36), state that the portraits of Frederick the Wise invariably turn to the right. Those of John the Steadfast, when facing to the left, were intended as pendants to Frederick the Wise. When turned to the right, they were used as part of a triptych with the three electors, or as independent portraits.
The Museum owns a second, almost identical, portrait of this sitter, also attributed to Cranach's workshop (MMA 71.128).