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In 2262, Shaw and James T. Kirk had a brief romance. Five years later, Lieutenant Shaw arrived at Starbase 11 and was assigned as the prosecutor in the court martial hearing that was convened against Kirk, following the alleged death of Benjamin Finney. Despite her previous personal involvement with Captain Kirk, Shaw carried out her obligations fully and impartially, and presented a strong case against Kirk. Kirk was cleared when Commander Spock was able to reveal that Finney was still alive and trying to frame the captain. (TOS episode: "Court Martial")
- Startrek.com indicates that Shaw and Kirk's relationship was in 2263 and thus only a four year difference between that event and the Finney case.
Following the completion of the court martial, Shaw struck a friendship with Kirk's defense attorney, Samuel Cogley. By 2287, Shaw and Cogley were married and had established a joint legal practice together on Earth. In that year, Cogley and Shaw both defended Captain Kirk at a number of hearings at the Federation Council over his involvement with the Klingons and the Nasgul. (TOS comics: "The First Thing We Do...", "... Let's Kill All the Lawyers!", "Trial and Error!")
In 2293, Shaw attended Kirk's memorial service that was held on the grounds of Starfleet Academy. Also in attendance were former crewmembers of the USS Enterprise and some of his other old "acquaintances". (TOS - Crucible novel: The Fire and the Rose)