In April 284 Ser James asked his grandfather and their steward to follow him outside. An envoy of House Jasper, on behalf of House Elesham, had arrived. A discussion followed in which the former captive, an old knight, a maester, and a younger knight convinced House Woodhull to meet with House Elesham. Iggy was adamant that House Woodhull must be recognized as equals by the Eleshams, but this point was lost in the discourse. Hoster expressed that they would begrudgingly meet on neutral ground at midday following the next full moon.

In February 286 Iggy attended the failed marriage brokerage between houses Woodhull and Elesham. Delegations from both arrived at the mid-isle clearing, but House Elesham brought 100 soldiers while House Woodhull, in good faith, brought only Ser James, Iggy, and the visiting Ser Brynden Tully (along with Thedore Jasper, Ser Darron, and Ser Dolins). However, when the Jasparparians abandoned the Woodhulls the situation quickly unraveled, with James wounded and taken captive, Iggy taken captive, and Brynden fleeing through the forest. In the following days at first light Iggy struck a deal with Lady Mya Elesham, under the watchful eyes of Ser Carsen Thorne, to oversee the Woodhull lands on behalf of House Elesham.

At the tourney on Pebble in 288 AC Iggy had the misfortune of meeting Clink Rivers on the morning of the final day. He and Lady Mya Elesham had been speaking with optimism about the promise Lord Pryor had as the new Marshall of the region before the discourse dissolved into trading barbs. Iggy spent much of the day wagering 1ss with Hugo on various goings on they could observe from the stands. Eventually Iggy even one 1ss from Teddy by betting on Ser Mikkel. As Mikkel was declared champion a dagger was buried in Iggy’s back; the old man bled out not long after.