Churchill's evening slippers and glass
Velvet evening slippers and a brandy balloon once owned by Sir Winston Churchill (1874-1965) were sold at auction on March 9.

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Three examples at auction this week showed collectors battling it out for mementos of the two-times British prime minister.

At Bellmans in Sussex, Churchill’s velvet slippers and brandy glass went under the hammer on March 9 while, on March 11, a cigar box was sold at Duke’s of Dorchester.

Churchill's velvet evening slippers

Churchill's velvet evening slippers – £32,000 at Bellmans.

The midnight blue velvet evening slippers from the 1950s monogrammed with his initials WSC and stamped N. Tuczek (a Mayfair shoemaker) were estimated at £10,000-15,000 and hammered down at £32,000. After strong bidding online between bidders in the UK and the US, a private UK collector was successful (paying £39,040 including buyer's premium).

Churchill's brandy glass

Churchill's brandy glass – £15,000 at Bellmans.

Churchill’s c.1960 brandy balloon, with large tulip-shaped bowl decorated in white enamel with monogram WSC and signed E Pope was estimated at £7000-10,000 and sold at £15,000 (£18,300 including buyer's premium).

Both lots were sold for the first time by Churchill’s family in the Political Sale at Sotheby's, on July 15 1998, where the vendor had purchased them.

Julian Dineen, Bellmans’ auctioneer on the rostrum, said: "Sir Winston Churchill is still highly regarded around the world and we had considerable interest from both the media and buyers that reflects that. It was only the second opportunity to acquire these wonderful items and the slippers in particular saw significant interest."

Churchill's rosewood cigar box

A rosewood cigar box used by Winston Churchill and given to his personal valet Norman McGowan – £61,000 at Duke's.

In Dorset, a large rosewood cigar box used by Churchill had been estimated at £5000-7000 at Duke’s and included two personalised cigars, an amber and gold cigar holder and a personalised penknife.

It had been owned by Churchill's personal valet Norman McGowan. The lot came with a photocopy of a previous auction catalogue description stating its provenance to McGowan.

With competition from bidders on the phone and online it was hammered down at £61,000 (plus 30% buyer’s premium incl. VAT) by 21-year-old Senan MacDonagh who on the rostrum for Duke’s. It sold to private British collector.


A personalised mother of pearl penknife inscribed 'Winston L. S. Churchill' from Churchill's cigar box.

Duke’s specialist Julian Smith spotted the box on a shelf when he was valuing items in a Devon home. He said: “It truly is one of those items that if you are lucky enough to discover you never will forget.”

Guy Schwinge, partner at Duke’s, added: "Churchill is rarely depicted without a cigar in hand, and the fact that he gave it to his personal valet gives it even greater resonance."

Cigar box

A rosewood cigar box used by Winston Churchill – £61,000 at Duke's.

On December 16, 2020, Sotheby’s New York sold Churchill’s 1940s leather briefcase which was knocked down at $28,000.

Art made by Sir Winston Churchill is also highly desirable and has gained hugely in price in recent years. Churchill's auction record was broken four-and-a-half times over earlier this month at Christie’s.

Tower of the Koutoubia Mosque was painted following the Casablanca Conference in January 1943. The British prime minister gave it to US President Franklin D Roosevelt ‘as a memento of this short interlude in the crash of war’.

Tower of the Koutoubia Mosque by Sir Winston Churchill

'Tower of the Koutoubia Mosque' by Sir Winston Churchill – a record £7m at Christie’s.

Having remained with Roosevelt’s son Elliot until 1950 and changed hands once since, it was bought by actor Brad Pitt in 2011 from New Orleans dealership MS Rau and given to his then-partner, the actress Angelina Jolie.

It was estimated at £1.5m-2.5m at Christie’s evening sale of Modern British art on March 1 and hammered down at £7m to a phone buyer believed to be from Belgium.

The same bidder also secured two further Churchill works at the same sale: Scene at Marrakech, painted as a gift for Field Marshal Bernard Montgomery Montgomery for £1.55m, and St Paul’s Churchyard which sold at £880,000. They were both underbid online from the US.

Before this sale, the highest price at auction for a Churchill painting was the £1.5m bid for The Goldfish Pool at Chartwell from 1932 which sold at Sotheby’s in 2014, a work offered from the estate of his youngest child, the late Mary Soames.