In an October 13, 2022 report from TV Line, the world learned that Gil McKinney will appear on "The Winchesters" as Henry Winchester: John's father and Sam and Dean's grandfather who spent time as a member of the mysterious yet significant Men of Letters organization. Technically, McKinney has already played the character on "The Winchesters," though it was only in a voiceover capacity. The publication notes that McKinney's Henry will appear in the flesh during the seventh episode of Season 1. It stands to reason this will be no problem for McKinney, seeing as he's got a fair amount of experience with the part under his belt already.
Gil McKinney's first turn as Henry Winchester came in "Supernatural" Season 8, specifically the episode "As Time Goes By." Via time travel, he convenes with Sam and Dean and alerts them to the fact that dark forces are after him in pursuit of a music box containing all kinds of powerful spells and scrolls. Following his time travel shenanigans, McKinney's version of Henry wouldn't reemerge until the Season 9 episode "Mother's Little Helper." This time around, he doesn't leap into the present to chat with his grandsons. Rather, he appears in a couple of flashbacks where he combats the demonic Abaddon.
Gil McKinney hasn't disappointed as Henry Winchester so far, so he'll more than likely impress once again when he returns to the character fully on "The Winchesters."
