Portfolio optimization in real-world financial markets is notoriously difficult due to non-stationarity, noisy data, and high transaction costs. Standard predict-then-optimize methods first forecast returns and then solve for weights, compounding prediction errors and often failing under regime shifts. We propose an end-to-end framework that directly optimizes differentiable surrogates of key financial metrics (Sharpe ratio, Omega ratio, Conditional Value-at-Risk, and risk parity), allowing neural networks to learn portfolio weights via backpropagation. Our expanding-window walk-forward procedure, applied to 50 S&P 500 stocks from 2007 to 2023, incorporates realistic bid-ask spread costs and rebalances quarterly. On the challenging out-of-sample test period (2022-2023), the best model, an AttentionLSTM with the Omega-CVaR-RiskParity loss, achieves an annualized Sharpe of 0.29 and a total compounded return of +7.86%, while the S&P 500 delivers -4.52% total compounded return and an annualized Sharpe of -0.02. This outperforms the S&P 500 by 12.38 percentage points, while keeping tail risk (CVaR) nearly unchanged. The framework outperforms the equal-weight portfolio, S&P 500, and traditional methods (MVP, HRP, NCO, ERC), demonstrating that embedding financial objectives directly into model training yields robust, economically meaningful outperformance even in adverse market conditions.

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