Lord John Grey, an officer in the British Army, makes his first appearance in Season 2 of Outlander as a 16-year-old English soldier who stumbles across a group of Scottish rebels, amongst them Claire and Jamie, on the eve of the Battle of Prestonpans. The young Lord John Grey immediately recognizes Jamie as “Red Jamie,” the wanted rebel, and assumes Claire to be his prisoner. Playing along, Jamie pretends to threaten Claire in an attempt to get information about the nearby British forces.
John Grey gives it to them, after which Jamie admits that it had all been a ruse and that Claire was, in fact, his wife; however, he decides to spare the young soldier’s life because he had so gallantly attempted to protect Claire’s honor. From there, we see Grey grow into a man in Seasons 3 and 4, with many twists and turns along the way.
This article will mainly focus on Lord John Grey's appearances in the Outlander TV series and, to a lesser extent, the main books, rather than on the character's own spin-off novel series.
Lord John Grey confesses his love to Jamie before having him flogged
While in Ardsmuir, Jamie soon builds up a reputation as the leader of the prisoners housed there. Despite declining to see Jamie shortly after being deployed as the officer in charge of Ardsmuir, Lord John Grey and Jamie soon develop a repertoire; spending many nights playing chess and discussing literature. It seems that their joint military background acts as a common ground upon which a friendship blossoms. One late night, Lord John Grey professes his love for Jamie by tentatively "making a move." Jamie immediately recoils, ridden with memories of Black Jack Randall, and severs the relationship with Grey.
Soon after this, a patch of Highland tartan is found in the cells. Jamie heroically claims responsibility for the illicit piece of cloth, forcing Grey's hand in having him flogged - a decision that seems to further injure the relationship between Lord John Grey and Jamie.
Jamie spends three years in Ardsmuir prison alongside Murtagh, but with the renovations to Ardsmuir drawing to an end; Lord John Grey is tasked with transporting the prisoners to the American colonies. Taking pity on Jamie, Lord John Grey decided to parole him to Helwater instead to serve the Dunsay family, with whom Grey was incredibly close.
Grey periodically visits Helwater to check in on Jamie's welfare (and perhaps for another game of chess). Jamie's time at Helwater forms his future path, especially after meeting Geneva Dunsay.
Whilst at Helwater, Geneva Dunsany develops a crush on Jamie and refuses to go riding with any stable-hand. On one fine day, Geneva (being her dramatic self) pretends to faint and fall off of her horse. Instead of catching her, Jamie watches as she thumps into the mud. Angered but seeing an opportunity, Geneva invites Jamie to her bedroom that night and threatens to tell her family that Jamie dropped her.
This night of forced intercourse eventually leads to Geneva falling pregnant and dying during childbirth. Jamie then kills Geneva's elderly betrothed, who upon seeing the baby immediately drew a knife to its throat.
Isobel Dunsany takes over the care of the child, who is then named William (known as Willie). Lord John marries Isobel in September of that year and legally becomes Willie's step-father. Upon his next visit to Helwater, Jamie begs Grey to take proper care of his illegitimate child; even offering his body in exchange. Grey declines, stating that he will care for the boy without payment; he is, however, pleasantly surprised when Jamie kisses him on the lips in gratitude.
Lady Dunsany offers Jamie his freedom after Geneva's death, but he declines for reasons unbeknownst to her. Jamie, in actuality, declined because he wanted to be closer to his illegitimate son, Willie. Willie soon starts to show the same aptitude for horsemanship as his biological father, Jamie, even leading to members of the Dunsany family saying that Willie and Jamie had been spending so much time together that they had even started to look alike.
Realizing that with each passing day, the resemblance between himself and Willie was growing, Jamie decided to leave Helwater behind.
Upon arriving in Jamaica upon the Artemis, Jamie and Claire are invited to a lavish ball at the governor's house. Soon after arriving, Jamie and Claire are introduced to the new governor of Jamaica - Lord John Grey. Shocked to see each other at first, and Jamie wishing to keep his connection with Grey as quiet as possible, the night goes on quite uneventfully. At least, until Lord John Grey calls Jamie to one side.
Lord John Grey tells Jamie of his son, Willie, and how he is progressing and growing up. He hands Jamie a miniature portrait of Willie, and for a moment they briefly embrace. Unbeknownst to them, Claire had been observing the entire interaction from a distance.
Realizing that the woman on Jamie's arm was the infamous Claire of whom Lord John Grey had heard so much, he decides to also approach her privately mid-ball. He explains how Jamie came to have a son and how he, Lord John Grey, came to be stepfather to the boy. Grey and Claire share mutual respect, as they both appreciate the space the other has taken in Jamie's life.
This revelation of a son comes as a shock to Claire, who is still rattled by the intimate embrace she had just witnessed, and who had been unaware that Jamie had sired an illegitimate son in her absence.
Ferreted away into the dark forests of Jamaica, Claire and Jamie are still frantically searching for the kidnapped Young Ian. Lord John Grey soon finds out about the predicament that the two protagonists are facing, and without hesitation, acts altruistically.
Lord John Grey offers the use of his Pinnace (a small sailing ship) to be used in the search for Young Ian; an offer that is gratefully accepted by Jamie and hesitantly by Claire. This might seem like a small gesture of friendship, but ultimately plays a large role in finding Young Ian; trapped by Geillis Duncan (who had been kidnapping boys in search of a virgin to sacrifice). Young Ian and Geillis Duncan are found in Abandawe (a cave). Whilst trying to free Young Ian, Claire kills Geillis Duncan. Ishmael, Jamie, and Claire make a break for it on none other than Lord John Grey's Pinnace - with the Porpoise following close behind.
Whilst acting as the governor of Jamaica, Lord John Grey sends for his wife Isobel Dunsany and his illegitimate son Willie. During their trip to Jamaica, Isobel falls gravely ill. Not long after starting to show symptoms, Isobel succumbs to "bloody flux," leaving Willie to complete the rest of his journey alone.
Jamie and Claire only learn of Isobel's passing en route to Jamaica after Lord John Grey shows up with Willie at Fraser's Ridge in Season 4. The death of the kinder sister, Isobel, does seem to weigh heavily on both Jamie and Lord John Grey.
Lord John Grey unexpectedly shows up at Jamie's new home in America, Fraser's Ridge, with young Willie in tow. Lord John Grey states that he felt the need to make the stop for various reasons; the main reason being for Jamie to see his illegitimate son. Lord John Grey and Willie prepare to travel back to Virginia, but before they can head-out Lord John Grey starts showing symptoms of measles. To protect Willie, Jamie heads off into the woods with him; away from the infectious disease.
Now left alone together, Claire and Lord John Grey both accuse one another of the other being jealous of the other’s relationship with Jamie. Claire tells him about Brianna, and he admits to Claire that he had been heartbroken at the time that Jamie had turned him down. Once Lord John Grey’s fever passes, he and Claire reconcile.
While staying over at Fraser's Ridge, Young Ian comments on the distinct similarities between Willie and Jamie, though his suspicions aren't confirmed outright. He grows even more suspicious as Jamie plays the role of a father; escorting Willie into the woods for a hunting trip, and far away from Lord John Grey's measles.
Although the books go into far more depth pertaining to this suspicion, it is also touched on during Season 4, perhaps foreshadowing a big reveal in episodes to come.