(covers information from several alternate timelines)
In 2268, Freeman served in the command division when the Enterprise was called to Deep Space Station K-7. During that mission, he was present in the recreation room where Uhura showed off the tribbles she had purchased from Cyrano Jones. When Uhura began giving away their offspring, Freeman spoke up and asked, "Say, Lieutenant. Seeing as you're giving them away, can I have one?" Uhura obliged, stating that she believed they were old enough to be adopted.
Later, Freeman, Montgomery Scott and Pavel Chekov entered the station's bar on K-7. (TOS: "The Trouble with Tribbles") At the time of his entry, Miles O'Brien had mistaken Freeman for Captain Kirk. Noting, "look at the way Kirk is ignoring that Klingon. He's letting the security officer handle it." However, Julian Bashir pointed out that he was wearing lieutenant's stripes. (DS9: "Trials and Tribble-ations") Moments later, Freeman was among multiple officers involved in a brawl aboard K-7, between the Enterprise crew and crew of the IKS Gr'oth. Freeman, however, later admitted to Captain Kirk that he was not responsible for starting the fight. (TOS: "The Trouble with Tribbles")
Due to a temporal incursion, however, caused by the presence of O'Brien and a group of fellow 24th century time travelers from the USS Defiant, a seemingly minor alteration was made to the timeline, as the Defiant crew also became involved in the brawl. As a result, O'Brien, instead of Freeman, was taken into custody by Enterprise security, and questioned by Kirk about his involvement in the brouhaha. (DS9: "Trials and Tribble-ations")
When the Enterprise itself traveled back in time to 1968 on a mission of historical observation and accidentally encountered agent Gary Seven, Freeman was called in to the transporter room to arrest him, accompanied by another security guard.
As they entered the transporter room, Kirk ordered them to have their phasers on stun and has them escort Seven to the brig until his story could be corroborated. Seven quickly attacked the security guard, while his cat, Isis, attacks Freeman, causing him to lose his phaser. As Seven attempted to activate the transporter, he was stunned by Kirk using Freeman's dislodged phaser. Kirk hands Freeman back his phaser and the groggy Seven was escorted away.
Later yet in 2268, Freeman found himself under the mind-control of Tommy Starnes, who was under the influence of Gorgan. Along with Chekov and a second security guard, Freeman tried to arrest Kirk and Spock with false orders from Starfleet Command. Kirk and Spock fought the three of them off and Mr. Spock took the trio to detention. (TOS: "And the Children Shall Lead")
|Chiefs of security of the starships Enterprise|
|Enterprise NX-01:||Reed (as armory officer)|
|USS Enterprise:||Pitcairn • Giotto • Freeman • Chekov|
|USS Enterprise-D:||Yar • Worf • Crusher|
|USS Enterprise-E:||Daniels • Worf|
|ISS Enterprise NX-01:||Reed (as armory officer)|
|ISS Enterprise NCC-1701||Sulu|
- "Trials and Tribble-ations" (archive footage)
Freeman was played by Paul Baxley.
Freeman was originally written into the script of "The Trouble with Tribbles" with the intention being a walk-on role for episode writer David Gerrold, a theater arts major. While Gene Coon had no objections at first, it was later decided that Gerrold was too skinny to be an Enterprise crewman, and the role was given to Paul Baxley, a regular stunt man, instead. (The Trouble with Tribbles, p. 211)
For his appearance in "Assignment: Earth", Baxley was credited as "security chief" in the episode's end credits. According to the 1 January 1968 final draft of the script, he was identified in the cast section as "Enterprise Security Chief Rawlings".
The original rank to be held by Freeman was that of an ensign, according to the revised final draft of the script for "The Trouble with Tribbles". Despite this, he worn lieutenant stripes, as pointed out by Bashir. In his next appearance as security chief, Freeman also wore lieutenant stripes, while in his final appearance, his uniform bore not no sleeve stripes.