Auto-bidding is an essential tool for advertisers to enhance their advertising performance. Recent progress has shown that AI-Generated Bidding (AIGB), which formulates the auto-bidding as a trajectory generation task and trains a conditional diffusion-based planner on offline data, achieves superior and stable performance compared to typical offline reinforcement learning (RL)-based auto-bidding methods. However, existing AIGB methods still encounter a performance bottleneck due to their neglect of fine-grained generation quality evaluation and inability to explore beyond static datasets. To address this, we propose AIGB-Pearl (\emph{Planning with EvAluator via RL}), a novel method that integrates generative planning and policy optimization. The key to AIGB-Pearl is to construct a non-bootstrapped \emph{trajectory evaluator} to assign rewards and guide policy search, enabling the planner to optimize its generation quality iteratively through interaction. Furthermore, to enhance trajectory evaluator accuracy in offline settings, we incorporate three key techniques: (i) a Large Language Model (LLM)-based architecture for better representational capacity, (ii) hybrid point-wise and pair-wise losses for better score learning, and (iii) adaptive integration of expert feedback for better generalization ability. Extensive experiments on both simulated and real-world advertising systems demonstrate the state-of-the-art performance of our approach.