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To help with writing my fics, especially the pre-game ones, I made this timeline for myself using dialogue/notes from the game, the official game guide by Piggyback, and the wiki (which is generally very good at linking back to its sources). And I figure other people might find it useful as well! For simplicity’s sake, when birth dates are ~approximate~, I just assume that it’s the correct year for latter age calculations. So:

~1844 – Hosea born

~1846 – Strauss born

<1849 – Uncle born

1855 – Dutch born

~1860 – Micah born

1863 – Arthur born. It’s implied that Dutch’s father died in the Battle of Gettysburg (July 1-3). Strauss arrives in America.

1866 – Bill born.

1870 – Dutch leaves home.

1873 – John born

~1875 – Dutch (20) and Hosea (31) meet (Dutch’s alliance with Colm possibly pre-dates this)

1877 – Dutch and Hosea run the Kettering con. Arthur (14) meets Dutch (22) and Hosea (33). Susan presumably joins them not long after. Abigail is born. Micah (17) is on the run with his father for a brutal double homicide. 

~1878 Hosea and Bessie try to leave the outlaw life (possibly the year before as Arthur was ‘too young to remember’?)

~1880 – Lenny born

1881 – John’s father dies, John is sent to an orphanage. Dutch’s mother, Greta Van der Linde, dies (but Dutch doesn’t know this until years later.)

1884 – John kills someone for the first time.

1885 – John (12) is rescued by Dutch (30), Hosea (41) and Arthur (22). Hosea and Bessie get their picture taken together.

1887 – First bank robbery. John is 14, Arthur is 24, Hosea is 43, Dutch is 32.

1892 – Bill is dishonourably discharged from the army.

1893 – Bill tries to rob Dutch, joins the gang

1894 – Abigail (17) joins the gang, gets pregnant.

1895 – Jack is born. Javier joins the gang. Lenny’s father is killed ~this year. Karen helps Arthur and Javier rob a bank between this year and 1897.

1896 – Jack is 1, John leaves. Sadie and Jake get married.

1897 – John returns.

1898 – The gang are in Montana, Copper eats all the salmon. Copper passes away. Jenny joins the gang. Micah saves Dutch’s life in a bar, joins the gang. Charles joins the gang. Lenny joins the gang late in the year.

1899 – Main game. Opening cutscene takes place in May. Arthur (36), John (26), Dutch (44), Hosea (55), Abigail (22), Jack (4), Lenny (19), Karen (mid-twenties) (can’t think of any other mentioned character ages??)

1907 – Epilogue. John (34), Abigail (30), Jack (12). Arthur would have been 44.