Leo had, up to this point in his life, never exactly been a ladies man although he enjoyed their company as much as most other men do.  He usually did not go out of his way to make an impression on them and his preference for nice clothes was more about putting forward the image of a successful gangster than any attempt to catch a woman’s eye.  The interaction with Jim Tunney’s girlfriend though had sparked something inside of him.  He had not made any advances toward her but she had apparently been very interested in him, at least up until the issue with his college degree came up.  Leo caught the idea that maybe he was more dapper and attractive than he had previously thought and so, in his down time and during days off, took to spending more time at social events and speakeasy’s.  A little more bold than before, he found that women did indeed seem to be interested in him and that it would not take much effort on his part to get them into bed.  By the end of January 1928 Leo had on-going relationships with five women and would exchange romantic and sometimes lusty letters with them in-between social excursions and trysts.  He kept every one of their return letters in a shoe box under his bed, a habit of collection that he would continue from then on, often giving up space in a suitcase for them during this later travels.   He was enjoying himself during this period of his life and several times thought back to the times in the past when he had been missing out on all of the fun he was currently having.  One day he even admonished himself that, “good old Stanley Bittenhopper had it all figured out back in Bakersfield, chasing the good times while I stayed home.”  It was a mistake he planned not to repeat in the future.

On February 10th of that year a letter arrived from his sister, one that curiously also mentioned Stanley.

Leo, brother – 

I received your letter and it was good to hear that you are well and doing fine.  Hopefully you understand that I am quite unsettled by having to take part in this ruse with you and the false names.  It is not something I think proper, although you are already aware of my feelings on this matter.   There is, however, a situation to which I object even more and that is having to deal with your criminal friends coming up to our family home to seek you out.  A young man appeared here two days ago, a Stanley Bittenhopper (his true name I suspect although who would know with these types you spend time with), and asked of your whereabouts.  I did not share what I knew with him as for all I know he is looking to find you for bad or notorious purposes.  He plans to stay in New Munich at least from what I can tell as he took a room at the Palmer’s.  He asked that I relay a message when next I was able to contact you, namely that he is wanting to know if you have work for him.  There, I have relayed it as I said I would, although I am certain it implies the worst kind of business and I do not wish to be caught up in this again.  You surely understand and will abide by this wish.  As for your other request, I will discuss the matter of the missing check with the bank and if they advise it to be without risk I will send another.  If not, than you will need to do without that money at least until you next return here, as I fulfilled my obligation in that regard when I sent it the first time.  Perhaps a more permanent address would get your issues with the mail settled in a more satisfactory manner.  Be well brother and know that I wish you the best despite your situation and choices – O

Leo smiley wryly when he was done reading, appreciating the scolding tone and dry humor of his sister.  He was surprised to learn that Stanley had found out where he was from, although he quickly remembered that his former partner knew his real last name and that had undoubtedly made things easier.  He also wondered if there might be a way to put Stanley’s talents to work on his bank robbery plans, although they would first need to discuss the money he had taken from Leo in Pomona.  He wrote back to Olivia, thanking her for her “supreme patience in putting up with her wayward brother,” and asking that she, “tell Stanley that I will keep him in mind and that he should give you his address.  And remind him that he owes me something,” before signing off with, “Your Brother, Leo.”   Right before sealing the envelope he pulled the letter out and added a short post script, informing his sister that she should not worry too much about Stanley as he was a gentle type of criminal.  

Leo continued to have a good run as time moved along into late February, maintaining his work with the local gang while managing his group of lady friends and scheming about bank robbery.  He was making enough money to get by but not nearly as much as he wanted to have, often lamenting that he really had not properly replaced his lost wardrobe.  He wanted to look sharp for the women and also to impress the local criminals, who he though of as beneath him, “lackeys seeking a leader,” as he wrote in one boastful letter to a female acquaintance.  He was confident and proud, certain that he was about to turn things around and would be able to get his own gang up and running soon.  He had even remarked in his journal that he had managed to stay out of the hands of the law for quite awhile despite being involved in several criminal schemes.  The law had chased him, even detained him a few times, but they never made anything stick and he had always been released or gotten away.  That was the mark of a professional he wrote, someone who, “had the edge on the police, someone to be respected.”  Two days later, on March 26, 1928, Leo’s luck changed.  

…to be continued