The photo shows him on board Shamrock IV on 1 July 1920.
Years before being elected, Lipton had challenged for the America's Cup with five successive Shamrocks. Photos of them are below with, from left to right Shamrocks I, II, III, IV and V:
1899: SHAMROCK I LOSES 3-0 TO COLUMBIA
Thomas Lipton commissioned William Fife III to design
his first challenger. She would be built by Thorneycroft of Millwall. Her hull was metal, with plating in aluminium above the waterline and manganese bronze below, on steel frames. At her launch the hull was covered "in petticoats" to prevent her lines being seen.
She crossed the Atlantic under a jury yawl rig (as most challengers did) and with internal bracing to strengthen her hull. With special permission from the NYYC, she was towed across for much of the voyage by Lipton's motor yacht Erin.
In the first race Columbia won comfortably, and in the second Shamrock I retired after breaking her steel gaff (all her spars were steel, as were Columbia's). In the
third race, Columbia led by just 17 seconds at the first mark but finished six minutes ahead on corrected time.
1901: SHAMROCK II LOSES 3-0 TO COLUMBIA
For his second challenger Lipton went to the more experienced Watson who carried out extensive tank
testing - with a dozen models made of paraffin wax over a period of nine months, so it is thought - before
drawing Shamrock II. She was built with hull plating in a light alloy called lmmadium by Wm Denny at Dumbarton.
On early sea trials her steel gaff collapsed and barely a
fortnight later, with King Edward Vll on board, her mast fell over the side when her bobstay parted. As a result
of this the Cup races were postponed for a month, and then for another five days when US President McKinley
was assassinated.
Shamrock and Columbia were closely rated (the challenger had to give the defender just 43 seconds per
race) and the races were close too.
Columbia won the first race by just over a minute and the second by three and a half, on handicap. In the third race, Shamrock II crossed the finish line just two seconds ahead, but lost by 41 seconds on corrected time.
1903: SHAMROCK III LOSES 3-0 TO RELIANCE
Lipton went back to Fife, although Watson helped him
with the design of Shamrock III. Dennys built her with
nickel steel plating on steel frames, and she was the first challenger with wheel steering rather than a tiller.
She lost her mast when on trials in Weymouth Bay, with the loss of a crew member.
She was accompanied to America by Shamrock I, her trial horse, the first to be used by a challenger.
However, she found herself up against the mighty Reliance, the Herreshoff-designed "skimming dish" and largest single-masted racing yacht ever built with an LOS of 201ft (61.3m) on a 90ft (27.4m) waterline and sail area of 16,156sq ft (1,500m2).
Reliance won the first race comfortably and the second narrowly. In the third race, thick fog shrouded the course and Shamrock III was temporarily lost, finishing 30 minutes after Reliance.
1920: SHAMROCK IV LOSES 3-2 TO RESOLUTE
This was the first America's Cup to be raced under the
Universal Rule.
Charles Nicholson, who had as little experience of the rule as any other British designer, drew Shamrock IV and she was built at his own yard in Gosport.
She had steel frames and her hull planking was in three
layers: the two inner ones were diagonal cedar and white wood, with fore and aft mahogany on the outside. She had a three-ton non-pivoting centreboard and a choice of sloop or cutter rigs. It was with the latter that she eventually raced for the Cup.
She was extraordinary looking, almost like the skimming dish rater classes of the late-19th century and Nicholson himself called her "the ugly duckling".
She was built in 1914 for that year's cup and was mid-Atlantic when the Great War broke out. The cup was eventually held in 1920 and things started well for the challenger when Resolute's throat halyard gave way in the first race, giving Lipton his first America's Cup race victory and Britain her first for over half a century.
Miraculously, the second then followed, as Shamrock IV won easily on corrected time in race two. She was one race away from winning the cup, and the third race was so close on the water that both boats finished with exactly the same elapsed time. However, with Shamrock IV having to give Resolute a massive seven minutes per race, that is the margin by which she lost on corrected time. That was Shamrock's last chance, for Resolute dominated the next two races, winning them by lengthy margins.
1930: SHAMROCK V LOSES 4-0 TO ENTERPRISE
This was an America's Cup of several firsts: the first for the J-Class and for bermudan rig, the first to be held off Newport, Rhode Island, and the first without handicap time allowances.
Shamrock V was Lipton's last challenger.
Just like his previous one, she was designed and built by Camper and Nicholsons. She had mahogany hull planking on steel frames, a yellow pine swept deck and a bronze-plated centreboard. There were ominous signs soon after she was launched when she was outpointed by the gaff cutter Lulworth at a regatta on the Clyde, but that was nothing compared to the stiff opposition she faced in America. The NYYC had four purpose-built Js from which to select a defender, and the boat that won the trials - Enterprise - proved to be superior to the challenger. Her duralim mast, for instance, not only weighed considerably less than Shamrock Vs wooden one, but its cost had reputedly been about the same as that of Shamrock V in her entirety. In the end, Enterprise dominated the best of seven series. Her smallest winning margin was three minutes.
But Lipton was enormously popular in America and later that year the Mayor of New York presented him with a solid gold loving cup as "the gamest loser in the world".