Churchill is not as uni­ver­sally loved as you imag­ine. Do you think he could do no wrong? 

No. Here are eigh­teen really bad deci­sions which can be arguably and author­i­ta­tively cited:

1. Desert­ing his nat­ural home, the Con­ser­v­a­tive Party, at an oppor­tune polit­i­cal moment (over the issue of Free Trade, which he later aban­doned) only to be forced to return to the Con­ser­v­a­tives afterward.

2. Going all-out to sup­port the Dardanelles/Gallipoli oper­a­tions in World War I with­out ple­nary author­ity to see them through.

3. Mis­judg­ing his First Sea Lord,  Admi­ral Fisher, who brought about his tem­po­rary polit­i­cal destruc­tion in 1915.

4. Restor­ing the Gold Stan­dard with­out com­men­su­rate reforms in tax­a­tion and wage policies.

5. Not lis­ten­ing to Bernard Baruch before invest­ing in the great Wall Street bull mar­ket in the late 1920s.

6. Wast­ing polit­i­cal cap­i­tal oppos­ing the India Bill in the early 1930s.

7. Try­ing to skewer Samuel Hoare on an issue of Priv­i­lege when Sam’s Tory friends could stack the deck to pro­tect him, despite his guilt.

8. Stand­ing up for Edward VIII in the Abdi­ca­tion Cri­sis, long after the King had lost the right to sup­port from anybody. Sir Mar­tin Gilbert’s chap­ter on the Abdi­ca­tion (Win­ston S. Churchill, Vol. 5) pro­vides the com­plete picture.

9. Launch­ing too late the Nor­way cam­paign of April 1940, although some of the delay was due to Cab­i­net dithering.

10. Plac­ing too much faith in the French Army in 1940.

11. Con­fus­ing the Ger­mans’ World War II Blitzkrieg with the sta­tic war­fare of World War I.

12. Believ­ing that cap­i­tal ships, like HMS Prince of Wales, were safe from hos­tile aircraft.

13. Believ­ing that Sin­ga­pore was invulnerable.

14. Believ­ing he could trust Stalin.

15 Com­par­ing Clement Attlee and the Labour Party to “a kind of Gestapo” in the 1945 Gen­eral Elec­tion.

16. Stay­ing on too long as Prime Min­is­ter in the 1950s.

17. Believ­ing that per­sonal diplo­macy would make a dif­fer­ence in Soviet behav­ior after Stalin’s death.

18. Not inter­ced­ing more force­fully to resolve the Anglo-American split over Suez in 1956.

Not every­body agrees with this list, but Churchill acknowl­edged some of it. In his book The Grand Alliance, over the Feb­ru­ary 1942 sink­ing of HMS Prince of Wales and Repulse, he writes: “The effi­ciency of the Japan­ese in air war­fare was at this time greatly under­es­ti­mated both by our­selves and by the Amer­i­cans” (Chap­ter 12). During the Blitzkrieg in France, he writes, “I was shocked by the utter fail­ure to grap­ple with the Ger­man armour, which, with a few thou­sand vehi­cles, was encom­pass­ing the ensure destruc­tion of mighty armies” (Chap­ter 3).

Some his­to­ri­ans con­sider the Dardanelles/Gallipoli cam­paigns unwin­able, even had Churchill been in charge: (In the ini­tial attack “by ships alone,” the Turk­ish forts may have been run­ning short of ammu­ni­tion, but their mobile bat­ter­ies weren’t; in the inva­sion of Gal­lipoli there was no recent expe­ri­ence in “com­bined oper­a­tions” to encour­age a suc­cess­ful out­come.) Oth­ers ques­tion what would have been gained even if had the fleet got through the Dar­d­anelles and appeared off Con­stan­tino­ple. Would Turkey have sur­ren­dered, as Churchill thought? These points are wor­thy of debate by thought­ful people.

Churchill’s faults like his virtues were on a grand scale. The lat­ter out­weigh the for­mer but, as Pro­fes­sor Paul Addi­son wrote, “I always feel that, para­dox­i­cally, it dimin­ishes Churchill when he’s regarded as super-human.”

See also a good, reflec­tive piece by Dou­glas Hall:  “Churchill the Great?” Why the Vote Will Not Be Unan­i­mous. 

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