This is a difficult question indeed! Many inspirational individuals held the post of British PM over the last centuries. They lived and worked in different times under different circumstances and different conditions. But it is easy to tell who are the worst. The ones who inherited the country great and left it in absolute shambles. There are a few men like that and, unsurprisingly, they were all Lefties! Despite the fact this cannot be challenged (all the Lefties bankrupted the United Kingdom over and over again) the intellectual class remain aloof. In the lastest University of Leeds poll of British intellectuals who are affiliated with the study of British politics/history, all the bad guys came out right on top. Back in 2004 as well as now in 2010 the poll found that in the 20th Century the greatest PM was Clement Attlee. Yes, Clement Attlee, the biggest socialist to ever rule Britain. Just once more for emphasis - the intellectuals chose Clement Attlee! What lunatic would do such a thing! The man is known chiefly for bankrupting the country through enormous entitlement reform, Keynesian devaluation of the Pound Sterling, rampant nationalization of all major industries and services, and creation of the National Health Service. All the worst policies and reforms in 20th Century Britain took place under this guy's nose, and they picked him as #1! I cannot think of a worse PM in all of British history! But - we all know how intellectual intellectuals really are... And where was the Iron Lady Thatcher, undoubtedly the greatest PM of the 20th Century, if not the greatest world leader of that century? A distant 4th behind the likes of Tony Blair...
Looking at the lists of greatest PM's reminds me somewhat of looking at lists of greatest US Presidents. Just as Attlee, Blair, and Lloyd George feature highly on British lists, so do Lincoln, F.D.Roosevelt, and T.Roosevelt on the American ones.
Just for the purpose of expressing my own personal opinion, here is my own ranking of the top 5 British PM's of all time:
1. William Ewart Gladstone
2. Margaret Thatcher
3. Robert Peel
4. Charles Watson-Wentworth
5. Arthur Wellesley
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