As a youth Crosby was apprenticed to John Young, a member of the
Worshipful Company of Grocers. He was made free of the Company in 1454, and became a wool merchant. By 1460 he was dealing on a large scale, and in 1462 was described as 'of London, grocer,
Merchant of the Staple of Calais'. In 1465 his former master, John Young, accused Crosby of 'counterfeiting his seal and making a false indenture', and the quarrel between the two had to be submitted to arbitration. By about 1469 Crosby was importing luxury fabrics, including damasks and satin, and exporting from England on Italian vessels. He was a
Member of Parliament for the City of London in 1467-68, auditor from 1467-8, and alderman from 1468 until his death. In 1469 he became Master of the Grocers' Company, and in 1470 was one of the two
Sheriffs of London. At about this time he was also Mayor of the Staple of Calais. By 1466 Crosby had amassed sufficient wealth from his trading ventures to obtain a 99-year lease of land from the prioress of St Helen's Priory in
Bishopsgate, and to build
Crosby Hall, a house which
John Stow described as ‘of stone and timber, very large and beautiful, and the highest at that time in London’. The house was later taken over by
Richard III; a scene in
Shakespeare's Richard III is set at Crosby Hall. In 1502
Sir Bartholomew Rede,
Lord Mayor of London, kept his mayoralty there. in April 1459 by
Henry VI, in 1464 by
Edward IV, on 10 February 1471 by the
Readeption government of Henry VI, and again on 11 December 1471. Crosby was one of the ambassadors sent by Edward IV to
Burgundy in 1472 and to
Utrecht and
Bruges in May 1473 to negotiate commercial treaties. Crosby made his will on 6 March 1471. He died five years later, in either January or February 1476, and was buried at
St Helen's, Bishopsgate, where an altar tomb was erected to him and his first wife, Agnes. He and his two wives are also commemorated in a stone inscription in the steeple of All Saints church in
Theydon Garnon, Essex. In his will, proved 6 February 1476, Crosby left cash bequests amounting to over £3200, in addition to lands and merchandise. His widow, Anne, was bequeathed £2000, while his daughter, Joan, was to inherit his manor of Hanworth. He also left £100 for the repair of
London Bridge, and a further £100 for the repair of Bishopsgate and the adjoining parts of
London wall. Crosby's manor of Hanworth was later acquired by
Henry VIII, while early in the twentieth century his former mansion in Bishopgate, Crosby Hall, was moved to
Chelsea, where 'it remains the only extant example of domestic architecture built for a London merchant in the Middle Ages'. The former site of Crosby Hall in Bishopsgate is now occupied by
Tower 42. Crosby's arms were
Sable, a
chevron ermine between three rams
trippant Argent, armed and hoofed
Or. ==Marriages and issue==