How would Cooper's hypothetical ambushers have missed getting all the money?
The way to deal with robbers is to give them your money not toss it in a river.
Think he might have dropped it seeing trouble ahead, intending to return, and the robbers didn't notice the drop?
Sure Cooper would have been accosted but if he had little or no money whats the point in dealing with him further after that is taken from him?
Taking what was in his wallet is unlikely to have spurred a killing.
Why would they kill Cooper if they hadn't robbed him of a very substantial sum?
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Quote Tom Kaye:
After 40 years, no body or other evidence has ever been found, suggesting that the idea Cooper died in the jump may be in error. A mechanical explanation has additional obstacles, so the processes that transported the money out of the woods and then twenty miles to the sand bar remains a mystery.
The money find on Tena Bar is complicated. The rubber band experiments allow less than a year for the money to become entombed in the sand.
The money continues to resist all natural explanations for how it arrived on Tena Bar. The story behind the money may be as big as the Cooper story itself. There is no hard evidence that Cooper died in the jump so it remains a primary debate. If Cooper walked out of the woods, there would certainly be easier ways to explain the money if human intervention was involved.
We tend to want to believe Cooper had full control, full clarity, a flawless plan, and 100% luck at all times in the full execution of his plan (whatever that was). The money ending up at Tina Bar seems to be an anomaly. Cooper could very easily have been trying to make his way back to where the crime started at Portland, for any number of reasons. The fact of money at Tina Bar suggests something went awry which could even include Cooper tossing the money off the railroad bridge at Vancouver himself. Maybe Bill Rollins is right and Cooper's primary goal was an exorcism of his grudge and the money was only a token of his revenge and not important to him in the grand scheme of things? You would have to have been there to know - or know Cooper personally.
I like what you said there about Cooper possibly trying to make it back to Portland. After all, he boarded the plane in Portland, so it wouldn't be far-fetched to think that's where he lived (or had a car stashed).
Now consider the fact that the drop zone and Portland are separated by the Columbia. So if he were trying to make it back to Portland, he would have to somehow get across the Columbia. Perhaps he was hoping to jump south of the Columbia but jumped too early? Either by miscalculation or was just experiencing a lot of anxiety and felt he needed to get off that plane.
So now he's on the wrong side of the Columbia. There are some bridges, but where? He doesn't have time to continue to travel so far out of his way to get to a bridge. It's cold, he may be injured, he fears the authorities are hot on his trail. The clock is ticking.
Is it possible he tried to cross the Columbia somewhere south of Tena Bar, went into shock and hypothermia and drowned? The money bag was swept downstream (north) to Tena Bar where a few bundles toppled out (remember that Cooper was pissed about the type of bag they gave him because there was no good way for him to close it shut) and then the rest of the bag continued on, maybe being launched out into the ocean? Cooper's body may also have been spit out into the ocean.
Now obviously attempting to cross the Columbia River (especially in the cold of winter) is idiotic. And while this was certainly not part of his original plan, crimes don't always go according to plan. It was a bold, risky, daring, crazy and DESPERATE move ..... a lot like hijacking an airplane and parachuting out.
Another possibility is that he was following the Columbia while trying to find a bridge so he could cross. He tucked himself under some brush for some warmth and rest and died of hypothermia (wouldn't be hard to catch hypothermia in that region considering how wet it is). The money was no longer tied to him at this point and the bag was swept away by a high tide in the spring from snow melt (and perhaps Cooper's body as well). He was south of Tena Bar at this time so the money floated downstream, made a cameo appearance at Tena Bar to topple out a few bills from the top before continuing on its way.
I think the fact that he boarded the plane in Portland and the money was found south of the drop zone (the direction of Portland) while also upstream of the drop zone is interesting and may suggest he headed south after landing.
Of course, this is all just pure speculation.