Starting an old diesel.

Oh yes you can! A fifty foot trawler in 1972, 5or6 cyl Baudouin, was started by being towed in gear, big prop, 5;1 gearbox. It was air start and the bottle or pipework was gone. I used to start a wing engine in gear, with help from the propulsion of the main, it was easier. 1936 Kelvin Ricardo.
Approx 15 years ago I was in a gale in the Dover Straits. I surfed down a big wave on a broad reach, slipped & accidentally kicked the engine into gear. A short while later I went below & found the engine, a Volvo MD 2020, ticking over
 
Eric Tabarley, I think.
Michel Desjoyeaux. In 2000, When he was leading the Vendée Globe. His starter motor collapsed & he tied a strap to the boom via some pullies. Released the boom & away she went. Story went that shore team told him to remove or release a couple of injectors to reduce compression first. Had to do it every couple of days..
 
My old 6L3 Gardner 114hp, 17litre, 900rpm, and weighing in at three tons including gear box, had hand starting gear. It consisted of an overhead shaft, with a handle at each end, with a chain drive down to a sprocket on the crankshaft. Each of the six individual cylinders had a decompression lever. The instruction manual stated laconically, "The engine driver may require assistance with this operation". I elected to do without the hand starting gear, and the engine always started very easily, including being able to be "bump" started, when making 4 or 5 knots through the water.
 
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