Tobias Finkelstein can occasionally be found playing Blackjack in Thieves' Landing, or walking around the Armadillo saloon.
- “I heard John Marston is quite foul-mouthed with the ladies.”
- — Tobias Finkelstein spreading rumors
- “I have to call my mother.”
- — Tobias Finkelstein talking
- Given the popularity of the scene and Rockstar's penchant for pop culture references, the surname Finkelstein could be a reference to Cheech & Chong's first feature-length film, Up in Smoke. In the film, Chong's character, Anthony Stoner, is being berated by his father for being lazy and unemployed. When Anthony is unresponsive his father threatens that if he doesn't find a job that day "we're shipping you off to military school with that goddamn Finkelstein shit-kid!".
- Tobias shares a character head with Roy Twaddle, Jeb Murphy, Coke Buckley, Grady Underwood, Gus McCallum, and Virgil Scoggins.
- According to Tobias, Jacob Ostenhaus is involved in an affair with Mrs. Winston.
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