He gained notoriety for an incident in Bedfordshire in 1904, where he and another officer confronted a group of youths who had been harassing them whilst boating, Winter killing one with a single blow from an oar when the boy attacked him with a wooden club.

In his autobiography, he recalls turning back a fleeing gun crew at revolver point on 1 May, helping to save a battalion of Royal Inniskilling Fusiliers from annihilation.

Mark Grant-Sturgis wrote of the Dublin Castle regime; "'O' is a marvel, he looks like a wicked little white snake, is as clever as paint, probably entirely non-moral, a first class horseman, a card genius, knows several languages, is a super sleuth and a most amazing original, he can do anything".

[4][5] Winter's detractors claimed him to be obsessed with cloak and dagger operations, at one point donning a disguise to personally seize part of IRA funds.

Leadership within the British Army were said to be initially unimpressed by Winter and later exasperated by his slowness in building a nationwide organisation, inability to set up a single intelligence system and by his lack of "an overall perspective.

Between February and March 1921, Fovargue would successfully infiltrate the IRA in England, which would suffer over 200 members arrested before the end of the conflict, providing information on their activities to Scotland Yard.

Amongst Winter's other ideas was 'The Raid Bureau', a 150-strong unit dedicated to analysing the vast amounts of paperwork generated by IRA leader Michael Collins.

Another innovation was collecting photographs of IRA members netted as results of raids and the establishment of local centres across the country allowing an exchange of intelligence between areas.

[18] During the first months of 1921, Sir Hamar Greenwood and others were declaring that the IRA was "near defeat," critically short of arms and ammunition and with up to 4,500 members interned in addition to hundreds more arrested.

[19] After his service in Ireland, Winter was put in charge of the resettlement of former RIC officers abroad, accompanied by police bodyguards and habitually carrying a pistol for 2 years afterwards.

However, the War Office vetoed his request, Winter having been resented by General Sir Nevil Macready and others over his attaining police primacy in intelligence matters over their Army preferred candidate, Lt-Col Walter Wilson.

In the 1920s, Winter joined the directorship of the burgeoning but badly managed British Fascisti, the first political organisation in the United Kingdom to claim and adopt the "fascist" label, which held several massive rallies -twelve thousand people one time- in London parks.

[20] The organisation's director was Brigadier General Robert Byron Drury Blakeney, ex Royal Engineers, who was in part responsible for the birth of the extremist Imperial Fascist League.