There are no shortage of uncertainties for the Philadelphia Phillies as they enter the 2020-21 off-season. After a 28-32 campaign in which they failed to reach the postseason for the ninth year in a row (the second-longest drought in Major League Baseball), the Phils have more questions than answers in front of them.
Will the front office prioritize signing J.T. Realmuto to a free agent contract after failing to sign him to an extension? Will the 2021 payroll decrease from 2020? If so, by how much? Do they re-sign shortstop Didi Gregorius to a free agent deal or will they fill that vital role with a lesser free agent, or internally with Jean Segura?