The selection of upper order statistics in tail estimation is notoriously difficult. Most methods are based on asymptotic arguments, like minimizing the asymptotic mse, that do not perform well in finite samples. Here we advance a data driven method that minimizes the maximum distance between the fitted Pareto type tail and the observed quantile. To analyse the finite sample properties of the metric we organize a horse race between the other methods. In most cases the finite sample based methods perform best. To demonstrate the economic relevance of choosing the proper methodology we use daily equity return data from the CRSP database and find economic relevant variation between the tail index estimates.