Charles Cheers Wakefield (1859-1941) was born in Liverpool, arrived in London in 1891 and became Lord Mayor of London in 1915. Wakefield supported the Guildhall Art Gallery from 1911 through subscriptions and commissions.

Works acquired by the Gallery with his help include Sir George Frampton's bust of Queen Mary, sculpted as a companion to Frampton's bust of George V, and Holman Hunt's The Eve of St Agnes. In 1927, Wakefield presented the Gallery with Millais's 1849 watercolour version of Lorenzo and Isabella and another royal bust, King Edward VII by Albert Bruce Joy.

Between 1936 and 1939 he gave the Gallery its collection of London watercolours by William Alister Macdonald, Henry Pether's Gun Wharf, Tower of London, David Roberts' small watercolour The Lord Mayor's Show at Westminster and a specially commissioned painting by Frank Salisbury, Coronation Luncheon at Guildhall, 1937: The Toast to the King. The Wakefield collection also includes Sir Peter Lely's portraits of Sir Edward Hales and his family, Sir Joshua Reynolds' Pope Paviarius and J. M. W. Turner's delicate watercolour view of Hythe, Wakefield's adopted home town.