Harry Longabaugh’s career as a train robber began less than gloriously when on Sunday, November 29th, 1892, he and two other unemployed cowboys, Bill Madden and Harry Bass, robbed the Great Northern No. 23 near Malta, Montana, getting away with only a few dollars. The amateurs didn’t take into account that banks were closed on Sunday and therefore the express boxes were empty. They would have fared much better had they robbed the passengers one of whom was carrying some $2,000 in cash. He’d planned to put it in the express car safe but had arrived at the station too late.
To add to the folly their bandanas slipped down during the heist making it easy for the crew to ID them. Not a good idea since, at the time, robbing trains was a capital crime.
After the robbery Madden and Bass unwittingly returned to Malta where they’d been hanging around for several days were recognized and arrested. During questioning they fingered Sundance as the third man but he managed to get away and headed for Wyoming where he eventually reached the outlaws lair at Brown’s Hole. Meanwhile, Madden and Bass took up residence in Deer Lodge at the Montana State Prison.