Closer to three decades than he is to two.
Born under a different name in Dale he grew up fairly simply. He was a cobbler's son with an absent mother, but a renowned cobbler at the time. His father made shoes for a number of high tier clients. As he grew from a boy into adolescence, he grew alongside a girl named Pella. As they matured, so did their friendship, and during their adolescence they blossomed into young love. It wasn't too long after Baelyre and Pella started wandering off for afternoons at a time that Baelyre returned home one night to find his father's shop had been ransacked, and his father was missing. Baelyre was always curious, and determined to find out what had happened, took it upon himself to investigate. The local guard concluded his father must've packed the essentials and left his son alone. Baelyre found evidence that a set of lowborn shoes were mixed up with the shoes of a new high tier client, and suspected that his father may have gotten himself involved with the wrong spoiled customer. He followed the notes in his fathers ledger and confronted the man, who waved him away and told him simply that his father was no longer in Dale. Baelyre asked the other employees and servants of this customer, and found that his father must be somewhere in Gondor, having been abducted from his shop as punishment and taken elsewhere to pay off debt. Being of age to be on his own, and having spent time with Pella learning alongside her a few things about the wilderness along the river and local wilderness outside of town, the two set out to find Baelyre's father.
To make a living during their travels, Baelyre would offer his services to solve local misdemeanors or strange occurrences. Missing chickens, stolen farm tools, highway robberies. It wasn't an easy journey, but that led him to gaining the fundamentals of fighting, even if he nearly never won any. It wasn't until he ended up in Minas Tirith that Baelyre found a plethora of problems to solve. As he conducted his business and searched for clues about his father, he met with a mysterious, brightly clad man offering him a full job. The man's name was Wolfgang. As Baelyre worked smaller and larger cases for Wolfgang, his status within Wolfgang's employ grew, and as the days turned into weeks, and the weeks turned into months and so forth, his fathers vanishing became a part of his past he simply let go of. Years went by. Baelyre and Pella married, and he established a small life for himself there. However, Baelyre started to work not only in the cities and nearby settlements of Gondor, but also was sent by his boss to further reaches, like Harwick and Snowbourne in Rohan. Once upon his return to Minas Tirith, Baelyre discovered quite shockingly that Pella had lost her affection for him, and had decided that his work was too demanding, and took a lover behind his back. Baelyre got into an argument with her, and they ended their marriage. It wasn't long after this her lover had beaten her and left her, and she came back pleading to Baelyre. He did not take her back, but remained a close friend of hers for a short time. Eventually, he found the pain of spending his time with her unbearable, unable to escape what she had done to him. He requested Wolfgang send him to manage cases in Rohan, and left Gondor for what he presumes to be for good.
Sometime during his tenure in Rohan, he received a letter from Wolfgang, instructing him to meet his employer in Bree...
To complete his jobs to the best of his ability