Pioneer Pipes was a meerschaum pipe & meerschaum lined briar pipe company based in Brooklyn, NY. Their meerschaum pipes were all marked with a fancy letter "P" (not to be confused with Peterson as above) & stamped "Genuine bLock Meerschaum". Impossible to know but you probably have an unidentified meerschaum pipe in a Pioneer Pipe case. It's possible they had a sister company that sold a line of seconds unmarked & under a different name. That was somewhat common back in the day.
It's an inexpensive tavern novelty pipe made of clay. Clay tavern pipes were originally sold at taverns & Kent to only be smoked a few times before they would usually break. Many yrs later they became more of a novelty item molded in many shapes such as your Indian.
Kaywoodie started as a line of pipes by KB&B in 1919, & the corporate name wasn't changed to Kaywoodie until in 1955. They made a lot of pipes. Most of their pipes have an inlaid cloverleaf on the stem. The cloverleaf changed some over the yrs & that can help date a pipe. If yours does not it could mean it has a replacement stem,
Don't know anything about John Cotton.
Never really understood these ceramic type of pipes. I guess just like the coffe grinders of the same era, it was all about the painting because they were not a good pipe. They don't breathe so they smoke hot & wet.
Novality stuff to catch the eye of the buyer. They bottom pipe probably is Cherrywood. Completely useless as smokers.
The camera lighter is neat but probably just a novality too.
I'm sure others will jump in & Ill have more to add when time permits in the next couple of days.
