CHESTER, Pa. – There are two things that have become abundantly clear in Earnie Stewart’s reign over the Philadelphia Union. He’s not one for lines of thinking that are hypothetical or hold no strategic value. And he’s a planner, someone whose target range for success isn’t always measured in a month or season but instead over a vaster period.



Those traits grate at each other along the fault line of a question posed to Stewart this week, his last full week on the job as the Union’s sporting director. He’ll decamp August 1 to take over as the general manager of the United States men’s national team after fulfilling half of the five-year contract he signed in the fall of 2015 to drag the Union’s soccer operations into modernity.



The results of that experiment, arguably the Union’s most salient investment in their future, are mixed. And as the ever pragmatic Stewart knows, his legacy in Chester is out of his...