On 14 March 1665 Sir Henry Bennet, secretary of state and prominent member of the king’s inner circle, was created Baron Arlington of Arlington in the county of Middlesex. His was one of nine new creations nodded through in the period between the beginning of February and end of March that year. The new awards were all the more remarkable at this point as Charles II had been relatively chary of making peerages since the great handouts of 1660 and 1661. Arlington’s promotion to the peerage at this point was thus remarkable – if only because he was one of relatively few people to be so honoured in the middle years of the 1660s. And yet, just how remarkable was it? For some, Arlington, ‘the inkhorn lord’ was a man of obscure background, whose rise was as rapid and extraordinary as it was distasteful; for others he was ‘Pimp Arlington’ and little better than a procurer of mistresses for the king. Arlington himself seemed to wish to emphasize his emergence from obscurity when choosing his new motto – ‘Haud facile emergunt’ (with what effort do they rise) – a bowdlerized inversion of a quotation from Juvenal. Arlington’s rise, this would seem to confirm, had been achieved in spite of life’s obstacles. Yet Arlington was far from obscure. He may have been a younger son, and thus limited in his original expectations, but he was descended from a long line of courtiers and parliamentarians and the number of his connexions is made clear by the fact that when considering what title he was to adopt Arlington was presented with a plethora of options reflecting his background and his relation to a variety of noble families. This chapter aims, thus, to reappraise Arlington’s origins, his connexions at court and in parliament, and to reconsider both how fair contemporary characterizations of him as a new man were but also why (if he was not as much an emergent as he might have wanted one to believe) he chose to adopt that particular guise.