We can account for the situation (bottom 6th, one out, up four) and calculate the breakeven rate by comparing win expectancies (The Win Probability Inquirer): WE before steal: 97.12% WE if successful steal: 97.38% WE if caught stealing: 95.86% Implied breakeven rate: 83% This shows two things: 1. You should believe that Hicks has an 83% chance of stealing 2nd in this situation before sending him. 2. Even in the unfavorable outcome (caught stealing), you still have a 95% chance of winning.