I don’t think it’s possible for the Tigers to re-sign Skubal. Scott Boras wants him to hit the open market. It’s good for his business.
The Tigers have no choice but to trade him next year. They need to have some control over his destination and send him to the NL. They can’t afford to let him walk for a compensatory pick and then sign with the Yankees, Red Sox, or Blue Jays. It would be disastrous losing him to a team that you have to face in a short playoff series.