An academically child who is gifted with learning disabilities is not readily recognised within the education system as demonstrating such contradictory traits. While there is a growing body of literature on such twice-exceptional children, effective means of identification and educational interventions still lags behind. To understand how this situation impacts individuals, an intensive case study of a young man, Thomas, with both gifts and learning disabilities was undertaken. Outstanding knowledge but an inability to demonstrate and express that knowledge meant frustration for Thomas. As a consequence, his disability meant that he manifested as a student with behavioural issues in the classroom, including a lack of self-control. At home he expressed his dissatisfaction with his education and specifically with his teachers. He had his own ideas of what his education should look like and how this could be implemented. This case study discusses the challenges his mother experienced with identifying her child's disability and giftedness and ensuring that both exceptionalities were optimally developed. Through this case study, the roles an education system and parents of such a child must assume, if this development is going to occur, are highlighted.