- For other uses, see Friedman.
By the late 2270s, Friedman was once again serving aboard the Enterprise as a security guard. In 2277, Friedman accompanied Admiral Kirk and Security Chief Galloway on a landing party mission to the Automate-66 pyrex plant on planet Marris V, along with Merlino and Pearson. After returning to the ship, Friedman became infected with a contagious bacteria spread by touch. He was incapacitated along with most of the ship's personnel by Morpheus-Nine gas and then cured with shots of a saline solution and vitamins. (TOS - Star Trek II Short Stories short story: "Wild Card")
Friedman, Galloway and Chekov were part of a preliminary survey team that explored Kappa Rho IV. He lamented to Chekov that the hot air and surface gravity of 1.84 Gs wasn't as inviting as Mura had been. Friedman sprayed and bandaged Galloway's lacerated leg after a large whatever-snake struck him from a cave, then gave him an immunizing hypospray. When several of the snakes attacked, he and the others used phasers to defend themselves. (TOS - Star Trek II Short Stories short story: "Intelligence Test")
Friedman beamed down in an environmental suit with a survey party to Omicron Theta V. Galloway asked him to gag and bind their insectoid ally Thrumwald so as to make him appear to be a captive. (TOS - Star Trek II Short Stories short story: "The Secret Empire")
When the Enterprise traveled through an unusually energetic ion storm, reality began to break apart. Friedman saw Galloway appear to change from a human into a dragon. (TOS - Star Trek II Short Stories short story: "To Wherever")