Montgomery Scott

2242: Started his first starship posting midway through his Academy time
2259: Rescued from Parnassus Beta by Christopher Pike;
Assigned to the USS Enterprise as an engineer
2265: Promoted to chief engineer of the Enterprise
2270: Assigned to refit crew of the USS Enterprise
2285: Promoted to captain while assigned to the USS Excelsior
2286: Assigned as chief engineer of the USS Enterprise-A
2293: Guest of honor aboard the newly-commissioned USS Enterprise-B
2294: Retired from Starfleet, lost aboard USS Jenolan on Dyson sphere;
Rigged the transporter systems, existed for 75 years in the ship's transporter buffer
2369: Discovered by the USS Enterprise-D, given his own shuttle to explore space