When members of House Jasper attempted to accost Uma for a bit of thievery he leapt to her aid, only stopped by Madsen’s command before blood was shed. This happened in a Gulltown tavern, 285 AC.

Leo participated in the tournament melee at Snownook in 285 AC. Early in the fray he did combat with Dolins and a mystery knight (paying homage to Jonquil Darke). The mystery knight eventually eliminated Leo with assistance from Dolins.

The final bout of the Spring Tournament of 288 AC saw Ser Argyle, Champion of the Fields, Ser Darron, Champion of the Sun, and Ser Leo, Champion of the Rains faced each other. A terse melee followed in which each man dished out and received substantial pain. In the show of martial prowess the oldest amongst them, Ser Darron, was victorious and named Champion of Spring. Lords Arryn and Royce raised his arms high as the crowd chanted ‘Darron!’, as the other two were helped from the proving grounds by Maesters.

In what became known as Ser Jamie’s Tourney in the region, in June of 288 AC, Ser Leo faced Ser Darron in the 3rd round. Despite scoring several solid hits against House Jasper’s Master-of-Arms, Lord Teddy Jasper called the match in favor of Ser Darron. Leo was wroth, feeling that he had been robbed by nepotism.