From what I've read, their investment into scouting/analytics is a decade plus behind just about everyone. Combine that with an owner whose largest contract ever given was $75M to Andrew Benintendi. They are the only team to never given out a $100+M contract. 2nd lowest is the Pirates $100M. The third lowest is the Cardinals $130M. So the third lowest team, has given out a contract nearly double the size of the largest the White Sox have ever given out.