Staggers fought the law, and the jury is still out on who was the victor.

Still having problems with troublesome wind, and everything else, Pineapple had a second stab at amplifying his guitar, with possibly even less success than before. Having heard that a guitar maker called Adolf Rickenbacker had produced an amplified lap steel guitar, called the "Frying pan", Staggers adapted a Harmony Regal parlor guitar by attaching a large griddle to the front with rivets obtained from an oil derrik construction site. Unfortunately, the power of the riveting machine was so great, all that was left of the guitar when he had finished was the headstock, bearing the logo "Harmony, steel reinforced neck". It was, but nobody could find it.
 Undeterred by this setback, the Pineapple connected the headstock to the panhandle, strung up the griddle, fixed on some cables and plugged into the mains, having completely misunderstood the principle of the magnetic pickup. The next four months of his career were spent in the burns department of Norfolk State Hospital.
 Upon his recovery, war was declared in Europe, Being a patriotic man, Staggers wanted to get involved and "do his bit". As soon as hostilities began, Staggers rushed down to the recruiting office of the Inverness and Clydesdale, Caledonian express steam packet and ferry corporation, and enlisted as an entertainer and spiritual advisor. Obviously, this was a non combatant role, as befitting a churchman, and also, as this was a fictional shipping line set up as a cover for the liquor smuggling operation of Borvington Smythe, the head of the West Norfolk branch of the notorious "Borvington Smythe" gang, he never actually had to go anywhere. Or do anything. Except store quite a lot of communion wine in his shed. Even though he didn't give communion. Or have a shed. So he kept it in Borvington's shed. Or warehouse. This lead to Staggers first serious run in with the law.
 The Pineapple, like many street musicians of his time , had had many minor run-ins with the authorities, and spent various periods of his life locked up in "the slammer". Some of his periods of incarceration where justified, and some less so, but all should be included in the story of his life.
 The first time he was arrested was nothing more than an accident of the police (as a lot of these things were, and still are!). As a young man, Staggers put a lot of effort into learning the songs of the older bluesmen in his neighbourhood, chiefly the great Samuel "Feathers" Tweak, whom he idolised. When Staggers was twelve, he felt old enough to show Feathers what he had learnt, and played both of his songs for him, and Tweak instantly replied "man that's some repertoire you got", before spitting on Pineapple's trousers and falling over. Staggers was so excited at being accepted by this great man that he ran up to the first person he saw and shouted "I've got a repertoire!"
 Unfortunately the first person he saw was a policeman who assumed it was a weapon of some sort, shot him , and then arrested him for possesion of an offensive repertoire and theft of a state bullet. He was subsequently cleared of possessing a repertoire, but sentenced to two years for bullet theft.
 Upon his release from Norfolk county Jail ,  Staggers vowed never to go back inside again, fine sentiments but a tough call for a street musician, and one he unfortunately didn't live up to. In fact, it was during a spell inside that Staggers met the great Huddie Ledbetter, in Huntsville prison, Texas.
Staggers knew of Leadbelly, as he had carried out an exorcism on a friend of Leadbelly's uncle, Terrell Ledbetter although he didn't actually meet Terrel. In fact it was this exorcism that got him thrown back into prison, as he was arrested on a charge of "improper use of a dwelling place as a place of industry", because he was paid eight cents for the exorcism and two cents per song (post demon), which made the house he performed it in officially a business address. It was this experience which led Pineapple to subsequently refuse payment for anything when inside any sort of building, and this caused him to develop rickets, malnutrition and bufonophobia.
 However, when he first saw Leadbelly, the great man was playing for the inmates a song called "State of Arkansas", also known as "Diamond Joe", a song which affected Staggers deeply, and there are many recorded instances of him speaking of this song, but none of him actually playing it.