Either:1) At the time, the position he was at made it a free skill pop2) The 14 to 15 pop salary increase happened but you didn't see it until the start of the new season when salaries updated
Use a salary estimator like on (http://www.buzzer-manager.com/)For your example, a player with all 10's going from 10 to 11 in JS: 19k to 23kFor your example, a player with all 10's (except JS) going from 15 to 16 in JS: 43k to 50kPlay around with it to estimate salaries after training and also where to get free pops.