This paper investigates the feasibility of developing bootstrapping mo
dels of criminal sentencing decisions to predict sentence length and t
he outcome of sentencing appeals. New Zealand Court of Appeal sexual o
ffence sentencing decisions are modelled as a function of variables de
scribing the character of the offender and the circumstances of the of
fence. The model outperforms both an equal weights approach and a naiv
e mean projection in predicting sentence lengths in a holdout sample.
As applications and further validations of the model, the disparity be
tween actual and predicted sentence is used to forecast the success of
an appeal and to predict change in sentence, given a successful appea
l. The results confirm that bootstrapping models have the potential to
contribute to a field traditionally believed to favour solely judgeme
ntal approaches.