Complex sentence: Although attending the University of Wisconsin for a time, Anderson eventually dropped out and, by 1907, had begun committing petty theft and would be in and out of prison in Illinois, Ohio and Wisconsin until 1914.
Split into simpler sentences: Although attending the University of Wisconsin for a time, Anderson eventually dropped out and, by 1907, had begun committing petty theft. He was in and out of prisons in Illinois, Ohio and Wisconsin until 1914.