The pit was untouched until 1849. A new corporation was formed with the financial backing to continue the dig. This group ran into the same flooding problems that occurred back in 1802. However they did manage to use a drill to probe what was below the money pit floor. A platform was constructed in the shaft just above the water level and the drill operated from there. The drill seemed to bore through levels of oak, spruce and clay. One sample recovered what appeared to be several links of chain made of gold.
While the drilling was going on, someone noticed that the water in the pit was salty and rose and fell with the tide. This led to speculation that the builders of the pit had conceived a clever trap designed to flood the pit with water if someone got to close too the treasure. Just who built this and what is it guarding?
The existence of the flood trap was confirmed by the discovery that the beach of Smith's Cove, located some 500 feet away from the money pit, was artificial. Examination showed that the original clay of the cove had been dug away and in its place laid round beach stones, covered by four or five inches of dead eel grass, which was covered by coconut fiber two inches thick and finally the sand of the beach. At the bottom of all this were five box drains that apparently merged somewhere well back from the coast into a single tunnel that ran the distance to the money pit. The system was apparently designed so that the filtering action of the coconut fiber and the eel grass would ensure the drains would never be clogged by sand or gravel from the beach. It worked well.
Attempts were made to put the flood trap out of business by building a cofferdam around the cove to by holding the tides back. Later, pits were dug to intersect and plug the tunnel on its route to the money pit. These failed, and this try at reaching the treasure was given up in 1851 when the money ran out.
The next attempt in 1861 cost the first human life. The searchers tried to pump out the money pit using the steam engine-powered pumps. A boiler burst and one worker was scalded to death while others were injured. Further fatalities were barely avoided when the money pit's bottom, weakened by attempts to get at the treasure by digging up underneath from other shafts, collapsed. If there were any treasure chests they were probably carried much deeper by this crash. This dig did succeed in discovering where the flood tunnel entered the money pit, but there was still no way to turn off the water. By 1864 these searchers were also out of money.
In 1866, 1893, 1909, 1931 and 1936 additional excavations were started. Extreme methods were used including setting dynamite charges to destroy the flood tunnel, building a dam to keep the water out of Smith's Cove, and bringing in a crane with an excavation bucket. None of these approaches recovered a single coin while costing the backers a small fortune and one worker his life. One of these efforts did manage to block off the flood tunnel from Smith's Cove, only to discover more water was pouring in from the opposite direction via a natural or man-made route from the south shore. Drilling also indicated that there might be some kind of cement vault at the 153-foot level. By this time the south end of the island was full of old shafts, though, and it was increasingly hard to tell were the original money pit was located. Searchers often ran out of money just trying to figure out where the old shaft had been.
