(covers information from several alternate timelines)
In 2268, Freeman served in the command division when he, Montgomery Scott and Pavel Chekov entered the bar on Deep Space K-7. (TOS: "The Trouble with Tribbles") At the time of his entry, Miles O'Brien misidentified Freeman as Captain Kirk. However, Julian Bashir pointed out that he was wearing lieutenant's stripes. (DS9: "Trials and Tribble-ations") Several minutes later, Freeman was among multiple officers involved in a brawl aboard K-7, between the Enterprise crew and Klingon 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. (TOS: "Assignment: Earth")
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 were put in the brig themselves. (TOS: "And the Children Shall Lead")
|Chiefs of security of the starships Enterprise|
|Enterprise NX-01:||Reed (as armory officer)|
|USS Enterprise:||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)
Background information Edit
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) Gerrold later had a cameo as an Enterprise security officer in "Trials and Tribble-ations".
For his appearance in "Assignment: Earth", Baxley was credited as "security chief" in the episode's end credits.
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". This appears to be reflected in "And the Children Shall Lead", where Freeman wears no rank insignia, signifying an ensign. However, on most other occasions, he continued to wear the rank of lieutenant despite script references from multiple appearances calling him "ensign". (The Trouble with Tribbles)