The timber trade middlemen are examined in this work to understand their functions, work conditions and work outcomes in the Caraga Region (Philippines) for development insights. Investigative practice and comparative observation were the approaches used to assess these middlemen. The results exhibit the essential role of the timber trade middlemen from log cutting to log delivery and in the regularity of timber trade operations across Caraga Region. Merchant middlemen, agent middlemen and service providers are the three general middlemen types observed. The service providers have the largest number and composition with six subtypes. Further results show that the purchase order holders (merchant middlemen) can profit largely (more than 20%) from the buy and sell of logs. The timber trade middlemen’s work conditions have issues with personal security, occupational safety, price uncertainty and transparency. They have been involved “incognito” in timber trade operations, rendering some of them vulnerable and less protected in the timber supply chain. Policy actions to enhance transparency and recognize properly these middlemen for the safe conduct of their businesses, for further skills development, for their organization in the timber industry, and for incentivizing their services properly are recommended for the sustainable development of the timber supply chain in Caraga Region.