Later Stein abandoned active anarchism and became a successful newspaper, pulp magazine, and book illustrator, while continuing to support Berkman and Goldman financially.
[2] The cousins shared an East Broadway apartment with a third Pioneer named Michelman, when their money allowed, or a park bench when it didn't.
[2] In 1889, the two moved into a four-room apartment on 42nd Street with Berkman's lover Emma Goldman, and her friend Helene Minkin[4] (who would later marry German-American anarchist Johann Most[5]).
They formed a commune inspired by Nikolai Chernyshevsky's novel What Is to Be Done?, trying to actualize their shared ideals of women's equality and cooperative living.
While the other three worked making clothing in factories or at home, Stein continued trying to become a professional artist, occasionally selling pictures, but mostly funded by the other roommates, or by money sent by his parents in Russia.
When he did sell one of his paintings, Stein would sometimes spend the money on "beautiful" luxuries, such as flowers, or fashionable clothes, which made Berkman fume.
Though Berkman admitted to possessive tendencies, he attributed them to his "bourgeois background", and worked to overcome them, as the three formed a successful ménage à trois.
In late 1890, the three lived in New Haven, Connecticut, with Helene and her sister Anna Minkin, while Berkman worked as a printer's apprentice, the women made dresses, while Stein continued drawing, but also tried making shirts, and his father's trade as a night clerk in a drug store, before all returned to New York.
This was relatively successful, so he invited Goldman to take orders, and in 1892, moved to Worcester, Massachusetts, to open the "French Art Studio", where Berkman also joined them to frame.
Initially intending merely to give speeches and spread pamphlets, news of the July 6 riverbank battle between strikers and Pinkerton agents inspired them to more decisive action, to serve as propaganda of the deed, namely to assassinate Henry Clay Frick, main company representative.
So on his way to blow up Frick's house with pockets full of dynamite, Stein—then still called Aronstam—saw a newspaper with a headline warning against "Aaron Stamm" as a Berkman conspirator.
[11] After Goldman was released in 1894, Stein moved in with her and her most recent lover, Austrian anarchist Edward Brady, for over a year, but did not resume his sexual relationship with her.
[15] In 1929, with his wife dead, and his daughter grown, Stein traveled to visit Berkman in Paris, and Goldman in St. Tropez, for her sixtieth birthday.
[1] Also in 1931 and 1932, Stein made multiple visits to southern France bringing large sums of money as gifts for Berkman and Goldman, essentially supporting them as their incomes decreased.
[24] When Goldman died in 1940, Stein drew a likeness of her for the bronze plaque on her monument,[25] which was eventually sculpted by Jo Davidson.