Oliver was present at the First Battle of Hoover Dam in 2277, and was also stationed at Camp McCarran before he left to be "present at Hoover Dam" according to Radio New Vegas. He meets the Courier in 2281 during the Second Battle of Hoover Dam. Through conversations with a number of non-player characters such as Chief Hanlon at Camp Golf, impressions of the general make him out to be someone who is eager for glory and victory at the expense of the lives under his command, as well as unwilling to listen to subordinates that may question his strategies; Boone suggests he owes his command to "knowing the president" i.e., sucking up to Kimball.
Many in the NCR disparagingly refer to him as "General Wait and See," due to his habit of being overly-cautious in battle, holding positions and only making aggressive moves when victory is practically guaranteed. His ultimate goal is to mass troops at the Dam in order to gain a decisive victory over the Legion - he feels only a total victory in a straight up battle of attrition would eclipse Chief Hanlon's tactical ingenuity and instrumental role in the First Battle of Hoover Dam; a victory frequently credited to Chief Hanlon.
If the Courier sides with the Legion or Mr. House, Lee Oliver shows his dedication to the NCR willing to fight to the death for its honor, but won't throw his men's lives away just for victory.
Eureka!: If the Courier sides with the NCR, General Oliver is the one to brief you on your objectives at the beginning of the battle. After the victory Oliver personally congratulates the Courier in the Legate's Camp.
All or Nothing, No Gods, No Masters: If the Courier chose either to work with Mr. House or to fight for an independent Vegas, Lee Oliver also appears after Lanius is dealt with. He can be talked down with a Barter, Science or Speech check (100) or killed by the Securitrons. Additionally, in a scene exclusive to the Independent path, if the General is convinced to tell his troops to stand down, the player character can then order him thrown off Hoover Dam, resulting in a cutscene where Yes Man throws Oliver over the side of one of the dam's watch towers.
Veni, Vidi, Vici: If the Courier has chosen to aid Caesar, General Oliver becomes the secondary antagonist, after President Aaron Kimball. The player character will need to battle their way through his defenses and reach his personal compound within the dam. There, Oliver can be persuaded to withdraw from the Mojave. If not, he escapes to his office, being protected by force fields. The Courier will then have to fight their way through to him, eventually cornering him and killing him.
If the player sides with the NCR, Oliver becomes a public hero, lauded for his leadership and strategic and tactical ability while more modest leaders like Colonel James Hsu and Chief Hanlon shy away from the limelight. He remains in the NCR Army following the Mojave campaign and continues to serve as its highest-ranking officer.
If the player sides with Mr. House, Caesar's Legion, or takes charge of an independent New Vegas and passes all the Speech checks needed to convince Oliver to withdraw rather than fight to the death, Oliver's military career is ruined by the NCR's failure in the Mojave campaign. If the player sides with him, Mr. House states in dialogue that there is a high probability that the General will eventually commit suicide.
If the player sides with Mr. House, Caesar's Legion, or creates an independent New Vegas and does not pass or attempt the Speech checks, Oliver stands his ground even in the face of total defeat and dies fighting.
According to Oliver, his mother died at an unknown point in his life.
Oliver has some manner of grudge against Colonel James Hsu, and is stated by Craig Boone to have interfered with Hsu's own career, preventing him from advancing past full colonel. Boone says that without Oliver getting in the way, Hsu would have been a general well before 2281.
Question on Joshua Sawyer's Formspring: General Oliver doesn't seem to grasp basic military strategy. What real life persons were an inspiration for his character? Would you agree Oliver's the main cause the war is going badly for the NCR?
He's a mishmash of various aggressive, blockheaded military commanders. Generals LeMay and Patton are obvious examples, though completely without the forethought of those two men.
During his final congratulatory speech to the Courier after they destroy the Legion Camp, Oliver mispronounces "plumed" (as it is written in the captions, referencing the colored horsehair plumes worn by the Legion) as "plumbed"