(covers information from several alternate timelines)
As a lieutenant, Nakamura served aboard the USS Reliant along with Ensign Jean-Luc Picard. While there, Nakamura voiced his strong views to Picard about snap inspections and the admirals who pulled them.
Despite his original reservations about them, he conducted a snap inspection of the USS Enterprise-D during its visit to the starbase. Nakamura agreed with Starfleet's ultimately unrealized plan to have Commander Bruce Maddox disassemble Lieutenant Commander Data for research. (TNG: "The Measure Of A Man")
In 2370, he was the commander of Starbase 219 when he invited Picard to the annual Starfleet Admirals' Banquet. Nakamura was hoping that he and Picard would have a chance to discuss Picard's new mission orders before the banquet. However, following the malfunctioning of the Enterprise-D’s new warp core, Picard was not able to attend the banquet. Nakamura was not pleased with Picard’s absence, believing the warp core malfunction to be yet another excuse for Picard to avoid the event. (TNG: "Phantasms")
Later that year, in an alternate timeline created by Q, Nakamura sent the Enterprise-D a priority one message notifying Picard that he had just ordered a fleet-wide yellow alert, noting that thirty Romulan warbirds were headed for the Romulan border of the Neutral Zone following the discovery of a spatial anomaly in the Devron system. Nakamura ordered fifteen starships to assemble along the Federation side of the zone, and ordered Picard to go there as well to investigate the anomaly. (TNG: "All Good Things...")