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Opened by the South Eastern Railway on 1 September 1866, the original station building was designed by Sir John Hawkshaw and J. W. Barry and was characterised by its two Wren-style towers, 23 ft square and 135 ft high, which faced on to the River Thames. The towers supported a 700-ft long iron train shed crowned by a high single arch, almost semicircular, of glass and iron.
To this was joined in 1867 an Italianate style hotel and forecourt designed by E. M. Barry which provided much of the station's passenger facilities as well as an impressive architectural frontispiece to the street. This arrangement was very similar to that put in place at Charing Cross. The station is carried on a brick viaduct over Upper Thames Street. Below this viaduct there are remains of a number of Roman buildings, which form a scheduled ancient monument. Barry's five-storey City Terminus Hotel underwent two changes of name: first to Cannon Street Hotel, and later, as an office block, to Southern House.
From 5-28 June 1926 the Southern Railway carried out various works, including the rebuilding of the platforms, relaying of the tracks and installation of a new system of electrical signalling - the four-aspect colour light scheme. The station was also renovated and the glass roof cleaned. The number of platforms was reduced from nine to eight, with five set aside for the new electric trains. The signal box spanning the width of the railway bridge was removed.
The station, which had been subject to structural neglect prior to the Second World War, suffered extensive bomb damage and was hit by several incendiary devices which damaged the roof. A high explosive also hit no. 8 platform. The original glass roof had been removed before the war in an attempt to save it. Unfortunately the factory in which the roof was stored was itself badly bombed, destroying the roof.
The station's prime location coupled with the property boom of the 1950s and the need for British Rail to seek alternative revenue streams made war-damaged Cannon Street a prime target for property developers.
Various plans were mooted for the reconstruction of Cannon Street Station, from the installation of a new ticket hall and concourse under Southern House in 1955 as part of British Rail's Modernisation Plan, to the construction of a car park and even a helipad.
In 1962 the British Transport Commission entered into an agreement with Town & Country Properties Ltd for the construction of a multi-storey office building above the station totalling 154,000 sq. ft. The cost of the development was £2.35 million and it was scheduled for completion by June 1965.
In preparation for redevelopment the remains of the once magnificent train shed roof had been demolished in 1958, and Barry's hotel (which had been used as offices since 1931) soon followed in 1960.
The architect selected to design the new building was John Poulson who was good friends with Graham Tunbridge, a British Rail surveyor whom he had met during the war. Poulson took advantage of this friendship to win contracts for the redevelopment of various British Rail termini. He paid Tunbridge a weekly income of £25 and received in return building contracts, including the rebuilding of Waterloo and East Croydon. At his trial in 1974 he admitted that shortly before receiving the Cannon Street building contract, he had given Tunbridge a cheque for £200 and a suit worth £80. Poulson was later found guilty of corruption charges and was given a seven-year concurrent sentence; Tunbridge received a 15-month suspended sentence and £4,000 fine for his role in the affair.
Poulson's building is remarked as being one of the most ugly of all station buildings in Britain, turning once a fine building into a hideous monstrosity. All that now remains of the original station architecture are the twin 120-ft red-brick towers at the country end and parts of the low flanking walls.
In 1974 the station closed for five weeks from 2 August-9 September to enable alterations to be made to the track and the approaches to London Bridge to be re-signalled. Traffic was diverted to London Bridge, Charing Cross and Blackfriars.
On 4 March 1976 an IRA bomb of about 10 lb exploded on an empty commuter train leaving Cannon Street, injuring eight people on another train travelling alongside. Had the bomb exploded 13 minutes earlier it would have caused widespread carnage as the train had been carrying commuters on the 7.49 from Sevenoaks.
On 15 February 1984 it was reported in The Times that Cannon Street would close. At the time, the station had been closed for weekends and evenings, and the publication of British Rail's new timetable for 1984-1985 revealed that it would lose all its direct off-peak services to the south-east. Services from Sevenoaks, Orpington, Hayes, Dartford, Sidcup, Bexleyheath, Woolwich, Lewisham and Greenwich would instead terminate at London Bridge except during peak hours. This was denied by British Rail which pointed out that it had invested £10m in re-decking the railway bridge, and that passengers travelling from the south-east during off-peak hours would most likely be visiting the West End and not the City.
In 1986 the station's twin towers, which had been Grade II listed in 1972, were restored in a £242,000 project. The works revealed that the east tower still contained a large water tank which was used during the days of steam to replenish locomotives and to power the station hydraulic systems. The brickwork was repaired, cleaned and re-pointed, and the weather vanes gilded to complement the dome of nearby St Paul's Cathedral. This work was one of the Railway Heritage Trust's first projects and coincided with an exhibition held in the station in August of the same year to mark its 150th anniversary.