He played his entire career with a team that regularly had the highest payroll in MLB. It was probably a tough transition to an organization running on a shoestring budget.
He and the core that won 5 championships all came thru the farm system. Jeter, Posada, Rivera, Williams, Pettitte. Add O'Neill whom they traded Kelly for and there is a pretty damn good core for the money.
The whole the "Yankees buy great teams" BS is just that.
Must have been shocking the first time he looked at their payroll. “Which player is getting this?” “That’s the whole roster.”