Large language models (LLMs) have shown strong performance across diverse financial tasks, yet portfolio management (PM), a critical financial decision-making task, remains poorly benchmarked. Existing benchmarks exhibit two main gaps: they ignore cross-asset correlation structures, thereby failing to distinguish genuinely diversified portfolios from concentrated ones, and fail to evaluate the complete PM decision pipeline in real-world scenarios. We introduce PortBench, a benchmark spanning six heterogeneous asset classes over ten years. PortBench consists of two complementary layers: a static QA dataset of 6,269 correlation-based questions across seven task templates, and a dynamic five-stage allocation pipeline that mirrors the full PM decision cycle. To evaluate these layers, we introduce two dedicated metrics: a dual-layer correlation score that measures whether proposed portfolios exploit inter-class hedging and avoid intra-class concentration, and CEPS, a metric that quantifies how reasoning errors compound across pipeline stages. We further assess strategy robustness and investor alignment under three historical stress regimes and risk profiles. Evaluating ten frontier LLMs, we find that despite strong performance on static financial QA, 90\% of model-profile combinations fail to outperform a basic equal-weight allocation, and models that satisfy every procedural constraint still suffer catastrophic drawdowns under stress. Our source code is available at \href{https://github.com/AgenticFinLab/portbench}{this https URL}.