How It Works
Each of the items was its own mini-puzzle and decoded to a word or phrase, except for the cigarette.
The cigarette was the framework for the other items. Continuing the theme of jamming paper inside small objects, the tobacco was all gone in this smoke, having been replaced with a rebus on a sheet of paper. Images of the rebus have been lost to Man, but rumor has it that the rebus featured images of the other pocket contents, so solving each of them for their word helped solve the rebus, and the rebus filled in gaps. Notably, "meat brick" was a component of the rebus.
Each bundle of paperclips formed a letter if you pulled it taught in the right way. The letters uniquely anagramed to the word CABLE.
The lone match in the matchbook was in the 3rd position, and it was sticking up, meaning "on" meaning binary. 23 is EIGHT.
The wad of paper was actually four pieces. The pieces were marked with origami fold lines. Teams who followed the fold instructions properly got PULL.
Knots were tied into the shoelace, overhand and figure 8. The figure 8's, being a longer knot, stood for a dash in Morse Code, and the overhand knots were each a dot. Reading from the shorter end of the shoelace yielded CHEWS (to be read as CHOOSE, in rebus style).
The bag in which the pennies came was important! It was a plaid cloth that made a 5x5 grid. Taking the pennies in order of year and laying them out on the grid gave this configuration.
The negative space forms a "2".
Plugging these words into the rebus created the nonsense statement "Chews 2 pull by cable metrick weights."
This type of clue is called a "charade"! Yay – I love charades! "Choose" is a synonym for PICK, "to pull by cable" is TOW, and "metric weights" is GRAMS. Put them together and you get the answer, which is PICTOGRAMS.
This puzzle all started from the idea that teams would find a body as part of their sleuthing, and the evidence would be the deceased's pocket contents. Dead body to raging bums, what a change. :)
Late the night before the Game began, GC realized this puzzle had never been properly verified. After checking each part, they were all clean except for the shoelace, which had an encoding error. “Encoding” meaning “all copies screwed up” (as opposed to a construction error). It was only off by a knot, but as luck would have it, that knot needed to be tied at the end with no slack—the end at which the tying had begun. So several members of GC devoted late-night hours to untying then tying all fifteen shoelaces.
The upshot is that, attempting to avoid tying hundreds of knots, GC also brainstormed several other ways to do an interesting encoding for this puzzle (while we tied the knots). You might see the results in a future Game.