Watch Now: Game Picks: Redskins at Giants (0:46)

Redskins coach Jay Gruden entered 2019 under difficult circumstances, with his starting quarterback unlikely to ever play again, his best player holding out over concerns about the team's management and medical staff, a suspect roster on offense and an owner who is not accustomed to being very patient with coaches. After three difficult weeks, it would not come as a shock to some on that staff if they were elsewhere by 2020, sources said, with the situation between the coaches and front office becoming untenable.

There have been several differences of opinion about the roster and specific players, with team president Bruce Allen holding all significant personnel power and Gruden, as well as general manager Doug Williams, sometimes unaware of major transactions or signings as they occur, multiple sources said. Allen's record in putting together a roster has been poor at best, and frustrations have grown since the start of last year, with some believing a rebuild was in order with quarterback Kirk Cousins on the verge of departing as a free agent in 2018. Allen, however, traded for Alex Smith and immediately extended him for $71 million in injury guarantees (Smith went on to suffer a career-threatening injury in 2018).

The holdout of star left tackle Trent Williams has further crippled the offensive line, but team management has dug in and not attempted to facilitate a resolution to that matter. Running back Adrian Peterson's roster spot has been an issue of contention as well, sources said. With the defense -- where most of Washington's talent is comprised -- faltering every week thus far, Gruden has been adamant about not considering any changes to his staff. Defensive coordinator Greg Manusky has long been under scrutiny there and his role is another potential hot spot between the coach and the organization, sources said.

At some point rookie quarterback Dwayne Haskins, the 16th overall pick, is likely going to play, and a decision will have to be made on whether or not Gruden is the man to oversee that transition. Sources said that Gruden is not inclined to play Haskins soon unless dictated by injury and would turn to veteran Colt McCoy should starter Case Keenum struggle (he turned the ball over five times in Monday's loss to the Bears). It remains to be seen if Allen and owner Dan Snyder share that vision for the quarterback position.

Team brass is high on first-time offensive coordinator Kevin O'Connell, sources said, after letting a slew of young coaches leave to find great success elsewhere in recent years. Washington has a former head coach on staff in offensive line coach Bill Callahan, who would make sense as the interim head coach should an in-season move be made.

Gruden, who is signed through 2020, is well-liked and respected among his peers, and there has long been chatter around the league that he would eventually join his brother Jon's staff with the Raiders should he not remain a head coach (Jon Gruden is in his second year of a 10-year deal with the Raiders). That team is set to begin play in Las Vegas in 2020. Jay Gruden is the only head coach under Snyder to get a second contract, but after six years in the long dysfunctional organization, some close to him believe a stint in a lower profile role with the Raiders would suit him perfectly.