Leland

Leland was a 23rd century Human, who headed Section 31 in 2257. 

Christopher Pike knew Leland pretty well, although when they met during the red burst investigation he had not seen Pike since before his hair went grey. One of his operatives, Philippa Georgiou, claimed that Leland was just a puppet following orders. 

Biography
At one point, Leland was involved in an incident where he was "up to his ass" in alligators on Cestus III. He claimed this to be the reason he transferred to Starfleet Intelligence. 

In the mid-2230s, as a young operative, Leland was involved with the time travel research called the Daedalus Project. In 2236, he worked with Michael Burnham's parents in the project on Doctari Alpha, and blamed himself for their deaths when the Klingons attacked the colony, which claimed their lives. $𝜇$ knew that he was responsible for the Burnhams' deaths. 

In 2251, Leland conducted a mission to Deneva that unfortunately involved the wrong ambassador. This incident was kept classified in his secure personnel file, but Georgiou was able to breach the firewall protecting his file to learn this information to later blackmail him to assist the USS Discovery. 

Later on Leland supervised Philippa Georgiou's mission to Qo'noS to shore up L'Rell's regime, and later ferried and Tenavik to Boreth. advised Leland that Tyler would be a strong asset to the organization. Part of Leland's intention had been to recruit Tyler for Section 31, but he left much of that task to Georgiou as well. He told her that she needed to work on her recruitment speech, but she fired back that her speech was just fine and that Tyler was in. 

After Spock fled Starbase 5, Captain Leland devoted significant Section 31 resources to find him. He would eventually capture what would later turn out to be illusory versions of Spock and Michael Burnham created by the Talosians. 

Following the destruction of Section 31's Headquarters, Leland and NCIA-93 rendezvoused with USS Discovery. Leland briefed the crew on the Daedalus Project and its connection to the Red Angel. After formulating a plan to capture the Red Angel, Leland went to Essof IV along with Discovery.

While orbiting Essof IV, Control took Leland captive, and killing him, reanimated his corpse via nanites, taking his identity. Posing as Leland, Control tried to lure Tyler and Georgiou into transferring the Sphere data to the NCIA-93, however, Georgiou discovered his plans, and prevented "Leland" from fulfilling "his" goal. "Leland" was able to escape via a shuttlepod. 

Memorable quotes
"Christopher."

"Leland."

"Is that gray hair I see?"

"Yeah, well, it's one of the trade-offs of having actual hair."
 * - Leland and Christopher Pike on their respective appearances

"There are always lives at stake. That's what keep us employed. See, we do what we do so you can do what you do."
 * - Leland to Christopher Pike on Section 31

Appearances

 * ("Bonus" deleted scene) (Season 1)
 * (Season 2)
 * (Also as a holographic duplicate, and reanimated by Control)
 * (Reanimated by Control, vision)
 * (Reanimated by Control)
 * (Also as a holographic duplicate, and reanimated by Control)
 * (Reanimated by Control, vision)
 * (Reanimated by Control)
 * (Reanimated by Control, vision)
 * (Reanimated by Control)

Background information
Leland was played by actor Alan van Sprang.

The character first appeared in the "bonus scene" deleted from the season 1 finale. In that scene, he was disguised as a Trill and Georgiou was able to deduce that he wasn't. He subsequently dropped his holographic disguise and was responsible for recruiting Empress $𝜇$ into the organization.