Lenny Summers

• ◆Lenny is Curzon Dobell's favorite character.
• ◆Both Lenny and Hosea stated in a random dialogue that they wanted to be buried with friends, foreshadowing that they would be buried together. The player may visit their graves after completing the mission "Fleeting Joy".
• ◆Hosea and Lenny's relationship mirrors Arthur and John's. Both relationships feature one member (Hosea and Arthur) being unsure about their more junior comrade (Lenny and John)—though in Arthur’s case much of his uncertainty about John comes from their strained dynamic due to the latter’s year away from the gang and abandonment of Abigail and Jack—but later grow to like them and eventually try to convince the other member to leave the gang. However, Lenny remains loyal to the gang until death, whereas John leaves to start a better life for his family following Dutch's psychological collapse.
• ◆It's apparent that Lenny had a crush on Jenny Kirk from the game's dialogue. He brings up the idea of giving her a proper burial in Colter, mentions her when playing Five Finger Fillet and Arthur and Hosea discuss his fondness of her. Micah is also implied to be aware of Lenny’s feelings for her, when he claims in a companion activity that he slept with Jenny and wonders if Lenny knows about it, prompting an annoyed Arthur to tell Micah not to tell Lenny about it.
• ◆Whilst at Horseshoe Overlook, he can be seen debating with Dutch over Evelyn Miller and his books. Lenny argues that the author is a fraud and that their gang is a better representation of American freedom than Miller's ideas, which causes Dutch to laugh and concede the argument, while jokingly telling Arthur (if the player is nearby) to be wary of Lenny’s intelligence.
• ◆Lenny's bandana is orange, in contrast with the usual black ones of the other gang members. The only others to not use black bandanas are Dutch and Uncle.
• ◆Lenny's primary weapon of choice is a custom Cattleman Revolver with a worn blackened steel look similar to John and Hosea's, as well as an ebony grip.
• ◆His secondary weapon is a custom Rolling Block Rifle in blued steel with a browned frame and a maple varnish. Sharing the same metal colors with Hosea's Semi-Auto Shotgun.
• ◆There is a letter at camp titled 'Letter to Lenny from Father'. In it, the writer mentions his own abandonment of his family, that he had been 'more tutor than father' and that he hoped his son's future was as a lawyer. It also states "you have redeemed more than you know, or can ever know, or should ever be expected to bear", tying in with the series' theme of redemption.
• ◆In a random encounter in camp, Lenny can be seen attempting to teach Sean MacGuire to read. Sean does not seem to want to, however, as he says it will "just put silly ideas in [his] head".
• ◆Lenny, along with John, Bill, Javier, Charles, and Sean, is one of the characters who may throw Arthur out of the camp if he antagonizes too many gang members.
• ◆After getting shot by the Pinkertons, Lenny appears to be still alive and breathing but the gang is forced to leave him behind during the escape across the rooftops.
• ◆How the Van der Linde gang reacts to Lenny's death paints a clue to their personality at the end of the game as well as within Red Dead Redemption. For example, Bill, Dutch, and Micah continue running without glancing (though Dutch does vocally express dismay), Charles stops and tries to help him with Arthur, Javier looks back at his fallen comrade before continuing, and Arthur attempts to help him before being discouraged by the gang.
• ◆Strangely, Arthur writes in his journal that Lenny got shot in the head when he was killed, even though he clearly sees Lenny get shot through the abdomen when the Pinkertons kill him.
• ◆Arthur comments that Lenny is not “even twenty years old.”

In story order, numbered as they are on the mission list. Not all of these are missions they hand you; some they only appear in.

Preaching Forgiveness as He WentLenny Summers

Coach Robbery (Lenny Summers)Lenny Summers