Since February 2012, Churchill is part of the Direct Line Group; policies are underwritten by the parent United Kingdom Insurance Limited.

This brought Churchill into RBS' insurance division alongside Direct Line – another company Long had been involved in launching.

[3] Following the bailout of RBS by the Government of the United Kingdom in 2008, the European Union demanded that certain group assets be sold off, including the insurance division.

In August 2000, Churchill became the shirt sponsor of Crystal Palace FC,[16] the football team Martin Long supported and would eventually share the chairmanship of.

[18] In the company's television advertising, the animated Churchill dog was asked whether he could save people money on their insurance and he responded with his catchphrase: "Oh, yes!"

The original adverts had Mortimer's voice responding to questions posed by his comedy partner Vic Reeves to a nodding dog mascot in the back of a car.

[21] Over the years many more ads were launched featuring the Churchill dog, including a campaign alongside such celebrities as Melanie Sykes and Roy Walker from January 2009.

In recent years, talking soft toys have been added to the range of Churchill merchandise,[24] and the character has a page on social networking site Facebook.

"[29] Churchill was once again redesigned in October 2019 for the company's new 'Chill' campaign, when his long-serving nodding dog design was changed to a realistic CGI version that no longer spoke.

[30] In January 2012, Churchill, along with sister company Direct Line, was fined £2.17m by the Financial Services Authority after being found guilty of altering complaints files.

[31] In February 2013, Churchill received media attention after it appealed against a High Court of Justice judgement in the case of Bethany Probert, who, in 2009 when she was 13 years old, was hit by a car driven by one of the insurer's customers whilst walking along a country lane.