Notes: The sign on the right says “New version of Sankatsu and Hanshichi at the Bar”. This refers to an old 1773 Kabuki theater production (艶容女舞衣) which is a tale of forbidden love between Sankatsu, a theater actress, and Hanshichi, a son of a bar owner who already has a wife named Osono. Long story short, they have a child out of wedlock, the families of Hanshichi and Osono oppose their relationship, and they eventually commit suicide together. The artist is implying that the relationship between Roosevelt and Churchill is like that between Sankatsu and Hanshichi, and that they will go down to their doom just like that forbidden couple.
This book excerpt explains parts of this play in English in more detail: https://books.google.co.jp/books?id=68RITdcFpHYC&pg=PA253&lpg=PA253&dq=Love+of+Hanshichi+and+Sankatsu&source=bl&ots=vXGDo8DwPS&sig=ACfU3U13cXTn4oQE9lvBKz5096kI3HiYBw&hl=en&sa=X&ved=2ahUKEwiUkbDblJ_1AhVQZ80KHYJ6B3QQ6AF6BAgOEAM#v=onepage&q=Love%20of%20Hanshichi%20and%20Sankatsu&f=false
There are also some play on words. “Roosevelt” sounds a lot like “loose belt”, so he is named 弛(loose)褌(belt), and he is depicted in the cartoon as loosening his belt. The “chill” in “Churchill” sounds a lot like the Japanese word “chiru” (disperse, scattered), and “Chur” sounds a lot like the Japanese word “cha” (tea), so he is named 茶盆(tea cups)散(strewn), to reflect the supposed downfall of Britain.
The article mentions a US representative from Arizona named Handerson who was allegedly an anti-war activist, but I could not find anyone by that name in the historical lists of Arizona representatives in the Arizona House of Representatives or the US House of Representatives.
(My translation of the article)
Gyeongseong Ilbo (Keijo Nippo), February 21, 1942
“I don’t know what to make of it” Roosevelt is cursed
The Fall of Singapore covered up in UK and US
Special telegram from Lisbon [sent on February 19]
According to the information from the US that reached us, the news of the Fall of Singapore provoked the US Congress and UK Parliament to the utmost, especially the US Congressmen who, in a state of excitement, crowded President Roosevelt to complain about the poorness of the British-American joint operation. Representative Handerson from Arizona, a leading figure in the anti-war movement, consulted with his colleagues in the House of Representatives saying, “I don’t know what to make of it”. He complained by bringing up arguments pinning responsibility on Roosevelt, saying “The breakdown of negotiations between the US and Japan last fall brought us misfortune. The President and the British Prime Minister are jointly responsible for this”. He asserted that his anti-war arguments were correct.
As a result, in the US states, anti-war groups have unexpectedly linked up with anti-production groups created in reaction to overproduction, and voices cursing President Roosevelt are spreading like wildfire. On the other hand, in the United Kingdom, which was choked with surprise at the Fall of Singapore as its colonial master, the announcement was made only to a part of the parliament, and the general public was not informed by order of the prime minister.
[Cartoon shows Mr. Roosevelt and Mr. Churchill]
Sign says: “New version of the Sankatsu and Hanshichi at the Bar” Narration: Mr. “Loose Belt” Roosevelt; Strings: Mr. “Teacups strewn” Churchill
Text says: “If we had only listened to Japan during last fall’s negotiations, we wouldn’t be in such grief.”
Reddit Link: President Franklin D. Roosevelt and Prime Minister Winston Churchill crying over the Fall of Singapore in 1942, “If we had only listened to Japan during last fall’s negotiations, we wouldn’t be in such grief” – Imperial Japanese editorial cartoon (translation in comments) : PropagandaPosters (reddit.com)
(My transcription into modern Japanese orthography)