We develop a new method for selecting the penalty parameter for $\ell_{1}$-penalized M-estimators in high dimensions, which we refer to as bootstrapping after cross-validation. We derive rates of convergence for the corresponding $\ell_1$-penalized M-estimator and also for the post-$\ell_1$-penalized M-estimator, which refits the non-zero entries of the former estimator without penalty in the criterion function. We demonstrate via simulations that our methods are not dominated by cross-validation in terms of estimation errors and can outperform cross-validation in terms of inference. As an empirical illustration, we revisit Fryer Jr (2019), who investigated racial differences in police use of force, and confirm his findings.