Born in TA 2988, Flynagin 'Alagnir' Newleaf matured quickly at a young age and through surprising circumstances. From barkeep, to diver to treasure-hunter to professional tree-climber; Flyn is a unique man of many professions. The road was quick to take the young and unsuspecting Combe-lander, and Rinni and Guvadan took him on as their mutual protégé through a series of fortuitous and frazzled journeys over many of his years: an expedition to Tharbad, a mining excursion at Iorvinas, a trade route to Forochel, two successful fight arenas in Ost Forod, and a caravan to Rohan... Just to name a few. These were succeeded by adventures aplenty of his own, scouring across Eriador with his 'ale and coin'-bound company in his quest of treasure and honor. 

While he often boasts proudly of his journeys, his exact motivations are a mystery to even his closest friends. Many fond memories were made in the company of his close friends and whichever other foreigners happened to be passing through, hearing and sharing stories of lands far and distant beyond Bree's hedge wall. At his very best, he is merry as ever, drunk more than sober, and rarely parted from his pipe. At the same time, however, it's not unusual for Flynagin to disappear entirely for periods of several months, only fueling to the air of suspicion around his lifestyle.

Just before war struck in Gondor, Flynagin Newleaf appeared in Bree one final time and hastily left with a company of well-intentioned sellswords that soon shaped into an ill-fated warband. Destiny intervened, however, and at Amon Sul, he was summoned to a gathering of his kin in Rivendell and eventually took part in the Passing of the Grey Company at the end of the Third Age.

Alongside his found kindred, he took part in the war, and on the day of his thirty-first birthday he claims to have played an instrumental part in lifting the hallowed siege of Pelargir. In a flitting moment, he met with Rinni and Guvadan once more, relieved to find them safe but quickly continued on with the war path. Honor had called him, and the two battles that followed tested every muscle and tested both his brawn and his heart. Earganon and Tamruben were among two of his companions to not return North and nor did many others. 

He remained in Gondor for a year after the King's coronation, only returning to his home of Bree in the autumn of the first year of the Fourth Age. While in Gondor, he split his time assisting with the reconstruction of Minas Tirith, visiting his family in Pelargir, and galavanting to Dol Amroth to try his penmanship as a scholar. He was content in maintaining his nomadic lifestyle in the South, where it seemed life was on the rise more than elsewhere, but fate guided him back home toward Bree. 

At first, he sought home to strive for a simpler life, but ere his arrival, he was heart-broken as he realized the horrors that swept through it in he and his kin's absence