Chaffin didn't tell us the whole story! This is a little strange since the Unity Church Parsonage where he lived could almost see the first house on Elm Street's Battle Row where Middleton lived between 1874 and 1881. Reverend Chaffin may have heard the sailor's stories but he apparently didn't listen carefully. While Middleton may have been discharged "from" the San Jacinto, he was actually sailing on another vessel at the time, a fact we'll examine in a moment.
The history of the ships themselves help us sort things out. We know Middleton left the army on July 7, 1861. Of his five ships only the San Jacinto was in the navy in 1861, and we know he wasn't on board until near the end of his service so what happened? Up in Boston the admirals were scrambling to find ships to maintain a blockade of the Confederacy. At the end of August they bought a large clipper ship called the Ino and converted it to military use. The USS Ino displaced 895 tons, had a crew of 144 and eight 32 pounder cannons. For us, the key date is its commissioning on September 23, 1861 exactly four years before Middleton's service ended. From July to September, he was either sitting home in Easton waiting to get a ship or working on converting the Ino. The Navy at this time was did not devote two months to training an ordinary seaman so I believe he was activated when the Ino was commissioned. The Ino spent the war looking for Confederate blockade runners and raiders and not finding many, but Middleton sailed thousands of miles in both the North and South Atlantic.
Beginning in November, 1863 the Ino was assigned to the East Gulf Blockading Squadron based in Florida and there she stayed until August 1, 1865. Leaving us with the problem of getting David Middleton back to Portsmouth to switch to the Roebuck and San Jacinto! My first (and second and third) thought was that Middleton never left the Gulf Coast after the Ino arrived there. The San Jacinto was at Key West often during 1863 and could easily have picked up crew from the Ino when she arrived in November. Remembering that the San Jacinto had captured a Confederate blockade runner called the Roebuck in January, 1864 perhaps Middleton became part of the prize crew. Unfortunately, none of this matches the dates set by Chaffin and prize ships were auctioned quickly so it's unlikely although not impossible that the prize ship was Middleton's Roebuck! Ugh! Thus the transfer from the Ino to the Roebuck or San Jacinto is the currently unsolvable problem.
The good news is that in order to serve on the USS Hibiscus Middleton had to be in the Gulf after the sinking of the San Jacinto since the Hibiscus, a brand new 406 ton propeller steamship only reached Key West in February 1865. After the sinking of the San Jacinto, Middleton could have been transferred to the tiny 45 ton Sea Bird, a captured blockade runner that the Union used to run into shallow harbors and river mouths. When the Hibiscus arrived in Key West, the Sea Bird became a tender assigned to the bigger ship giving Middleton an easy transfer to finish his service.
So, if you have been following this convoluted puzzle what do we have? Chaffin was clearly wrong by implying, if not actually saying, that the San Jacinto was Middleton's last ship. The Hibiscus/Sea Bird tandem had to be what Middleton sailed on in 1865, and since the Hibiscus was decommissioned at New York on August 19, 1865 while the tiny Sea Bird was sold at auction at Key West in June, it was the Hibiscus that brought Middleton home. We also know that Middleton spent the most time on the USS Ino, but when he transferred to the San Jacinto and the Roebuck (and which Roebuck) remains a mystery. At any rate, dear reader, for sticking with me this far here's a picture of the Hibiscus:
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