The White Sox didn’t land any of the great players during free agency
The Chicago White Sox were supposed to sign free agents to supplement the young core that they were building. Rick Hahn made it seem like they would be in on everyone available that could help them win.
The failure here started in the off-season ahead of 2019. Bryce Harper and Manny Machado were both available. They were younger than most free agents of their status because of how early they came into the league.
Harper ended up with the Philadelphia Phillies and Machado ended up with the San Diego Padres. The White Sox claim that they tried to get both but the offers to them weren't good enough.
In hindsight, those guys never had a realistic shot at coming to the White Sox. Since then, they have missed just about everyone. Their bad ways of doing business plus being cheap are the biggest reasons why.
As long as the current ownership group is in place, the White Sox have no chance of becoming a team with sustained success year after year. All of these big problems step from Jerry Reinsdorf. It is time to sell.