The first submariner to be awarded the Victoria Cross was Lieutenant Norman Holbrook, captain of HMS B11. He received Britain’s highest award for gallantry after his boat sank the elderly Ottoman pre-dreadnought battleship Messudieh (alternatively Mesudiye) on 13 December 1914.
The British Admiralty, keen to move as many ships as possible to the Grand Fleet, had proposed that the blockade of the Dardanelles be left to the French. However, the threat from the German battlecruiser Goeben, now flying the Ottoman flag, meant that the French insisted that the British battlecruiser HMS Indefatigable should remain.
Consequently, the blockading force consisted of Indefatigable, the light cruiser HMS Dublin and the French pre-dreadnought battleships Gaulois, Vérité, St Louis and Charlemagne, the armoured cruiser Amiral Charner and seaplane carrier Foudre. Each navy also contributed six destroyers and three submarines.
The British submarines were B9, B10 and B11 of the B class. Although only eight years old, the rapid pace of development of submarines meant that they were obsolescent by 1914. They were designed for coastal patrol work with a range of 1000 nautical miles at 8.75 knots surfaced, a maximum speed of 12 knots surfaced and 6 knots submerged, an armament of two 18 inch torpedo tubes and a crew of 15. The petrol engine used on the surface made conditions for the crew even worse than in later diesel powered boats.
They had hydroplanes on each side of their conning towers to improve underwater handling, an innovation that was not repeated until US nuclear submarines were similarly fitted for the same reason 50 years later.
The Ottoman navy was active against the Russian one in the Black Sea, but sat on the defensive at the Dardanelles. The Messudieh was positioned as a stationary guard ship.
The Allies conducted an active submarine campaign in the Dardanelles from December 1914, two months before the Gallipoli campaign began with a naval attack and four months before the first troops were landed. There was, however, a bombardment of the forts at the mouth of the Dardanelles by British and French warships on 3 November 1914, five days after the Ottoman fleet attacked Russian bases in the Black Sea, but two days before Britain declared war on the Ottoman Empire.
Entering the Dardanelles was difficult for submarines even without the Ottoman minefields because of the current and differences in the layers of the water that made it hard to manoeuvre underwater. The British submarines were more manoeuvrable, and thus more successful, than the French ones.
On 13 December 1914 B11 was chosen to be first Allied submarine to enter the Straits. They were protected by five lines of mines, but her diving planes were fitted with special guards to prevent her becoming tangled up in the mines’ wires.
Holbrook dived his boat underneath the mines, succeeding in passing them despite the strong current. He then came up to periscope depth, spotted a large enemy warship, closed to 800 yards range, fired a torpedo and dived. After hearing an explosion, he brought his boat back to periscope depth and saw that the enemy ship was settling by the stern.
The return journey was made more difficult by the fact that the lenses of B11’s compass had steamed up, making it unusable. Holbrook was not even certain where he was and had to estimate the time that it would take to clear the minefields on the way home. B11 bumped along the bottom several times. Eventually, he felt it safe to return to periscope depth. He could then see the horizon and steer for it. However, the compass was still unusable. B11 returned to base after being submerged for 9 hours to learn that she had sunk the Messudieh.
Holbrook’s VC was gazetted on 22 December, making it the first ever awarded to a submariner and the first of the war to a sailor to be announced. Commander Henry Ritchie’s VC was given for an act of gallantry on 28 November, but gazetted later than Holbrook’s. Every member of B11’s crew was decorated: Lieutenant Sydney Winn, the second on command, received the Distinguished Service Order and the other members of the crew either the Distinguished Service Cross or the Distinguished Service Medal. The DSC was awarded to officers and warrant officers, the DSM to petty officers and ratings.
The citation for Holbrook’s VC, taken from this website, stated that:
For most conspicuous bravery on the 13th December 1914, when in command of the Submarine B-11, he entered the Dardanelles, and, notwithstanding the very difficult current, dived his vessel under five rows of mines and torpedoed the Turkish battleship “Messudiyeh” which was guarding the minefield.
Lieutenant Holbrook succeeded in bringing the B-11 safely back, although assailed by gun-fire and torpedo boats, having been submerged on one occasion for nine hours.
Note that English spelling of Turkish names differ.
The Ottomans blamed the loss of the Mesudiye on the Germans, who they said had insisted on putting her in an exposed position despite their opinions. She sank in shallow waters, making it possible to cut holes in her in order to extract trapped men. 37 men were killed out of a crew of 673. Many of her guns were salvaged and used in shore defences of the Dardanelles.
In August 1915 the town of Germanton changed its name to Holbrook. Norman Holbrook visited Holbrook several times and his widow donated his medals to it a few years after his death. His VC is now on display at the Australian War Memorial, with a replica on show in Holbrook near a model of B11.
 J. S. Corbett, H. Newbolt, Naval Operations, 5 vols. (London: HMSO, 1938). vol. ii, pp. 70-72.
 R. Gray, Conway’s All the World’s Fighting Ships, 1906-1921 (London: Conway Maritime Press, 1985), p. 87. This source has been favoured where its information differs from the Wikipedia entry linked in the text.
 P. G. Halpern, A Naval History of World War I (London: UCL Press, 1994), p. 119.
 Corbett, Newbolt, Naval. vol. ii, p. 72-73.
 Ibid. vol. ii, p. 73, note 1.