He was born in Wakefield, Yorkshire, the son of Joseph Bailey and his wife Susannah. Susannah was the sister of Richard Crawshay, the Ironmaster based at Cyfarthfa Castle near Merthyr Tydfil where Crawshay Bailey came at the age of twelve to work for his rich uncle in 1801, joining his elder brother Joseph. In 1809 he was a witness to his rich uncle's Will, in which he was bequeathed the sum of £1,000 (equivalent to £55,000 in today's terms 2007 ).
Along with his elder brother, Joseph, later Sir Joseph Bailey, 1st Baronet, Crawshay went into the iron business as a young man in 1811 at Nantyglo and soon at Beaufort, Ebbw Vale. He became a Partner, with his brother in 1820.
Though by now a major ironmaster he far-sightedly bought up large areas of coal-rich land, at their agricultural value too, in the Rhondda Valleys, at Mountain Ash and Aberaman and was prepared to sit on these assets for nearly nine years before developing them as some of the richest coal and iron ore deposits in the world.
In a similar manner he waited until the most auspicious time before applying for a Parliamentary Act to open and run a railway company. In 1845 he was instrumental in setting up the Aberdare Railway, along with Sir John Josiah Guest to capitalise on further assets in the form of sinking new collieries and building new blast furnaces.
He was anti trade union and opposed to his workers organising themselves along these lines.
He had already been appointed High Sheriff of Brecknock in 1837 and also held the same office in Monmouthshire in 1851. He was Member of Parliament for Monmouth Borough from 1852 to 1868 and was elected in five successive parliamentary elections.
By 1867 he owned iron works, blast furnaces, coalmines, tramways, railways and brickworks. He retired in this year, selling off all his assets over the next three years and retiring to Llanfoist near Abergavenny, where he lived in Llanfoist House. A local park in Abergavenny town is named Bailey Park in his honour.
He died in 1872, aged 83, after at least seventy years in industry. His only son, and heir, Crawshay Bailey II (born 1821), inherited.