As a youth, John de la Pole married twice; his first marriage was annulled, but his second marriage, to Elizabeth of York, made him the brother-in-law of two kings, Edward IV and Richard III. It brought him eleven children, the eldest of whom, John, would eventually be named heir to Richard III in 1484 and die in battle in the Yorkist cause. John de la Pole, though, generally managed to steer clear of involvement in the tumultuous events of the Wars of the Roses. Although he was politically aligned to the House of York by virtue of his marriage, he avoided participating in the battles of the 1450s, not taking up arms until Edward IV had claimed the throne. De la Pole appears to have spent much of this period, in fact, feuding with his East Anglian neighbours, the Paston family over an inheritance – even interfering in parliamentary elections, for example, in an attempt to gain the upper hand.