Through conversations with a number of non-player characters such as Chief Hanlon at Camp Golf, impressions of the general give the impression that he's 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. Oliver is highly political, and Boone suggests he managed to get promoted past Colonel James Hsu by "knowing the president", i.e. sucking up to Kimball.
Oliver is not especially popular in the NCR Army. Within the ranks, he is commonly referred to as "General Wait-and-see," "Old Wait-and-see" or "Wait-and-see Oliver" due to his habit of being overly-cautious. Oliver's preference is to focus on holding ground already gained, strengthening logistics and combat support before acting, and to not make any offensive moves if he deems them too risky, something that happens often. Oliver's ultimate goal is to mass troops at the dam in order to gain a decisive victory over the Legion, a battle he knows is coming.
Oliver has an ulterior motive for his heavy focus on the coming Second Battle of Hoover Dam. Chief Hanlon, the much-admired leader of the NCR Rangers, emerged as the public hero of the First Battle of Hoover Dam in 2277, despite the fact that Oliver was in overall command. This has grated on Oliver and his ego ever since, driving him to deliberately contradict Chief Hanlon on tactical and strategic matters as the Army gets ready for the coming Second Battle of Hoover Dam.
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 significant 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.
Oliver is the highest-ranking NCR Army commissioned officer in 2281, and the top-ranked officer in the Army to appear in the game.
"Do you know what you're doing? Making a nation - like you think you're doing, ain't like chowing down on a pile of Fancy Lad Snack Cakes. Think you got the guts to to carve out a frontier? Build towns, protect the roads, run supplies, train troops?"
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"
↑Craig Boone's dialogue: "Wasn't real popular, though. Even overheard my C.O. complain about him once. General Wait-and-see, he called him."
↑Colonel Hsu's dialogue: "And in the meantime General Oliver won't approve any offensive maneuvers because he doesn't want to risk losing our positions."
↑Chief Hanlon's dialogue: "Oliver can't stand that rangers got credit for victory at Hoover. Whatever I recommend, he does the opposite."
↑Mr. House's dialogue: "No need to worry about the General, by the way. He'll be held responsible, publicly disgraced... 36.5% probability of suicide, by my estimate... Kimball won't be able to save him - he'll be too busy getting thrown out of office."