You Can’t Win by Jack Black – Review

I recently read the book “You Can’t Win” by Jack Black, an autobiography of a safecracker (or yegg) who lived in the late late 19th and early 20th centuries.   The timespan between them and now is long enough for everything to be very different, but recent enough for the differences to be recognizable.  It was the best book I’ve read in quite some time.

Surprises in the book

  • There was a coherent alternate criminal society – the criminal element really did seem to all know each other – much more than I would have expected anyway.  The “underworld” seems to be an accurate name
  • Criminals really did have separate names for everything, i.e. yegg, pegging, “On the square”
  • Crime was very widespread – people did not mix criminal and straight jobs
  • Criminals specialized to a surprising degree
  • Beggars were highly valued by other criminals (as they saw everything that happened in a city)
  • Opium use was quite widespread – apparently the author maintained an active drug habit while in (American) prison with no difficulty whatsoever
  • Prisons were not overcrowded
  • Canadian prisons where somewhat more officially brutal (with lashings!) but there was no unofficial brutality – and extremely well run – I imagine both the criminal and taxpayer would prefer the Canadian system of the time to the American
  • The “silent” system and single cells seemed to  solve the prisoner on prisoner violence problem
  • The age at which parents sent children to be on their own is surprisingly low – 14 seemed to be quite common
  • The bonds between parent and child seemed to be much less than now
  • The author was sentenced to 2 years and 30 lashes in his Canadian prison stint – 15 on the way in, and 15 on the way out.  Good behavior would have the authorities go easy on him with the final lashes
  • Jail sentences were less than expected
  • People regarded the notion of identity very differently – There were no permanent records, no widespread photography, no fingerprints, no nothing.  Basically you were who you said you were unless someone said different.  And you could move 50 miles away and never run into anyone you had ever met
  • Many, many more

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