The Redskins are hopeful something can be worked out with the Pro Bowler who held out last season; some people close to Williams also have cautious optimism.
"We're working through the details," Redskins coach Ron Rivera told reporters this week at the NFL combine in Indianapolis. "We're in a good place, a good conversation and we're going to go from there."
But plenty of questions -- and scenarios -- remain.
Are the Redskins closer to resolving Williams' concerns?
Williams was pretty clear on his stance with former Washington president Bruce Allen: He didn't trust him. And last season, Williams told ESPN that he felt Allen refused to trade him out of vindictiveness.
Williams also was upset with the medical staff and how a cancerous growth on his scalp was handled. Several people in the organization last fall expressed their disappointment over those comments because he wouldn't tell them who on the medical staff upset him. But they did fire head athletic trainer Larry Hess; there were also complaints from other players about Hess.
Had the Redskins not made those moves, there's no chance Williams would have wanted to return.
But here's the flip side: Rivera also must be convinced Williams wants to be with Washington. He's a new coach inheriting a 3-13 team that hasn't won more than nine games since 2012. Rivera also needs to know that if the Redskins decide not to give Williams an extension and he plays out the final year of his contract, it won't become an issue in the locker room.
What's the holdup now?
The meetings with Rivera were a necessary first step. But another big hurdle remains. In December, Williams told ESPN that beyond Allen, the sides were far apart on other issues. In other words: money. Williams has a $12.5 million base salary for the final year of his deal, none of which is guaranteed.
Multiple people say Williams wants to be the NFL's highest-paid tackle. It's not far-fetched at all considering his résumé: He's a seven-time Pro Bowler who is always in the discussion when it comes to the game's best left tackle.
Philadelphia right tackle Lane Johnson signed a four-year deal worth up to $72 million. Johnson also received $25 million fully guaranteed at signing. Williams could aspire to top this, and there's another player who could bump up his salary: Laremy Tunsil. The Houston tackle also has one year left and could be in line for an extension that could surpass Johnson.
"The Redskins need to make a compelling [contract] proposal that makes sense for Trent to give up [free agency in 2021]," said J.I. Halsell, an NFL agent and former salary-cap analyst with the Redskins. "[Otherwise] if you're Trent, why not roll the dice on yourself and wait for next offseason to have someone pay me $19 or $20 million?"
Why not trade Williams if the Redskins don't extend him?
That would make sense, but what are the alternatives? The Redskins don't have another player on the roster capable of starting at left tackle, and unless they trade the No. 2 pick in this year's draft to get more selections, the Redskins -- who don't currently have a second-round pick -- won't be drafting a tackle until at least the third round. They want a strong protector for quarterback Dwayne Haskins Jr., which might be hard to find if they move Williams.
Keeping him without an extension might postpone the inevitable, but it buys Washington a year. The Redskins could then draft a tackle in 2021. They probably would receive a third-round compensatory pick in 2022 after Williams signs elsewhere. It's not an ideal situation, but if they went this route, it would allow them to focus on filling other needs in 2020.
"To me, it's either extend him or trade him," said former NFL agent Joel Corry, who is now a salary-cap expert for CBS Sports.
The best way to find a tackle worthy of replacing Williams would be to trade the No. 2 pick, moving back several spots, and drafting one in the top 10. That could mean passing on defensive end Chase Young and, possibly, cornerback Jeff Okudah or linebacker Isaiah Simmons. Keeping Williams another year allows the Redskins to draft whom they want in April -- not whom they need.
What could Washington get in a trade?
The Redskins, a source says, remain hopeful they could get a first-round pick for Williams. But others believe a second-round pick might be more likely. A handful of teams picking in the second half of the first round could use a tackle, including Miami (picks 18 and 26), New England (23) and Minnesota (25). But the Dolphins have been in a youth movement, New England didn't want to pay Williams when there was talk of interest last summer and the Vikings have little salary-cap room.
Williams' talent and a weaker free-agent field at the position helps him -- and the Redskins. But he's also 31, hasn't played a full season since 2013 and has been suspended twice for violating the NFL's substance-abuse policy. Those factors would limit his value, but as one member of the Redskins' organization said in the fall, anyone who wonders if Williams can still play at a high level needs only to watch his 2018 tape.
Is there a cap penalty if the Redskins trade or release Williams?
Williams' total cap hit is $14.5 million this season. The Redskins would have $2 million in dead cap money (from a $10-million option bonus he received in 2016) but the other $12.5 million in base salary would come off the cap. That would bump Washington to about $73 million in cap space, allowing it to perhaps find a stopgap in free agency, draft another tackle and try to develop him for the future.