When Freeman, Montgomery Scott and Pavel Chekov entered the bar on Deep Space K-7, Miles O'Brien thought Freeman was Captain Kirk, although Julian Bashir pointed out that he was wearing lieutenant's stripes. (DS9: "Trials and Tribble-ations")
Several minutes later, Freeman was among the officers involved in the brawl aboard K-7 between the Enterprise crew and Klingon crew of the IKS Gr'oth. Freeman, however, was not responsible for starting the fight. (TOS: "The Trouble with Tribbles")
However, the presence of O'Brien and his fellow time travelers of Deep Space 9 from the 24th century caused a minor change in the timeline, as they got involved in the brawl. As a result, O'Brien was taken into custody by Enterprise security instead of Freeman. (DS9: "Trials and Tribble-ations")
When the Enterprise traveled back in time to 1968 on a mission of historical observation and accidentally encountered the 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 and along with Chekov and another Security Guard Redshirt 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:||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|
Freeman was played by Paul Baxley.
Freeman was originally written into the script with the intention being a walk on role for the 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, pg. 211) Gerrold later had a cameo as a security officer in "Trials and Tribble-ations".
In "Trials and Tribble-ations", O'Brien mistakes Freeman for Kirk; in the original series, Paul Baxley was a regular stunt double for William Shatner.
The original rank to be held by Freeman was that of an ensign, according to the revised final draft of the script. This appears to be reflected in "And the Children Shall Lead", where Freeman wore 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)