CHICAGO – As Chicago Bears first-year general manager Ryan Poles evaluated his players during their preseason opener Saturday, the most pressing assessment centered around a player standing on the sidelines in a T-shirt and shorts.

What to do with Roquan Smith?

The 25-year-old linebacker is considered by some to be the Bears’ best player, but on Aug. 9, he asked to be traded after talks broke down regarding a contract extension. Smith is heading into the fifth and final year of his rookie contract.

“The deal sent to me is one that would be bad for myself, and for the entire LB market if I signed it,” Smith said in a statement, adding that the new regime doesn’t value him and refused to “negotiate in good faith.”

Poles consistently praises Smith, and he did so again Saturday. “I love the player,” he said, expressing hope he will eventually suit up for the Bears.

But there are several complicating factors, including the fact that Smith isn’t represented by an agent. His lack of representation came into focus Monday when the NFL contacted all 32 teams to inform them someone is improperly gauging trade interest on Smith’s behalf. The complicated process of working out a trade is why at least one agent believes Smith will fall short in his pursuit. But another agent said the trade request was the right move. With the Bears nearing their regular-season opener on Sept. 11, Poles is on the clock to resolve a situation that continues to grow more unclear.

How does not having an agent affect Smith’s situation?

Smith has represented himself the past two years after firing agent Todd France, who has more than 60 clients, including Dallas Cowboys quarterback Dak Prescott and Los Angeles Rams defensive tackle Aaron Donald.

Several high-profile players have negotiated top-of-market deals without an agent, but with the help of advisers. Seattle Seahawks first-round pick Charles Cross thanked his business manager, Saint Omni, for helping guide him through the process. Omni is the director of football at Lifeline Financial Group and the subject of Monday's NFL’s memo.

The league management council sent the message stating Omni, who is not an NFLPA certified agent, has been contacting clubs indicating he is a representative of Smith. The memo stated Saint is prohibited from negotiating player contracts or discussing potential trades on behalf of any player.

The memo also referenced Article 48 of the collective bargaining agreement that states player contracts are to be negotiated only with the player, if he is acting on his own behalf, or the player’s NFLPA certified agent. The memo ended with a reminder of the league’s anti-tampering policy, which states that “no Club is permitted to negotiate with a player under contract to another Club, or with his certified agent, or to discuss a potential trade without the direct written permission of the player’s employer Club.”

The Bears have not granted Smith permission to seek a trade, sources told ESPN.

Some players who self-represent receive guidance from the NFLPA’s salary-cap and agent administration department.

“[The NFLPA] can tell them the marketplace and where they think he should stack up and the type of a deal, but [NFLPA reps] haven't had the dialogue with the team,” an agent said. “So they don't know if there were issues in the past. They don't know where talks have stalled. It's not just about your play. It's not just about money. It has to do with where the team is and what the regime is and what the opportunity cost is.”

Baltimore Ravens quarterback Lamar Jackson is negotiating what is expected to be a massive long-term deal without an agent. Jackson, who’s in the last season of his rookie deal, said he’s going to halt negotiations once the regular season starts.

“One of the more difficult things about being self-represented is you’re everything -- you're the asset and you're the negotiator,” an agent said. “We care a lot about our guys, but I would assume if you're talking about your own income and generational wealth, you're going to get a little more heated than those of us who do this year in and year out and kind of know this is just how it goes.”

And some players might find it more comfortable to let a representative handle negotiations that can become adversarial.

“You can put pressure on them, you know when to pull, when to push,” an agent said. “You know timing, you have the ability to have off-the-record conversations elsewhere to understand what the market is. You have an understanding of what the issues may be. You have an understanding of precedents.

“He doesn't know any of that, unless someone's actually helping him with it.”

Which side has the leverage?

The Bears have the leverage. Smith is under contract this season for $9.7 million after the Bears picked up his fifth-year option in May 2021. If there is no extension or trade, Smith doesn’t have much of a choice but to play on his current deal.

If he isn’t on full-pay status -- which means an active roster spot, injured reserve or PUP -- for at least six games during the regular season, according to the CBA, he would not accrue credit for the season and be eligible for unrestricted free agency next year. And his contract would toll, meaning the Bears would have his rights for the 2023 season at the same amount he’s set to earn this year. If Smith were able to demonstrate “extreme personal hardship causing such failure to report or perform,” that could be a mitigating factor, according to the CBA.

And while it’s unknown whether the Bears are fining him for being healthy but not participating in practices, Smith will get fined during the season if he sits out.

“That discipline really comes from the front office,” first-year head coach Matt Eberflus said recently about fining Smith during camp. “I’m not going to get into the details of what discipline is there. But we will certainly work through that when the time comes.”

Even if Smith does play this season, the Bears could place the franchise tag on him in 2023, which is projected to be $18.291 million for linebackers.

Which players can Smith look at for salary comparisons?

The Indianapolis Colts’ Shaquille Leonard and San Francisco 49ers’ Fred Warner reset the market for off-ball linebackers when they signed extensions last offseason. Leonard, who was the Defensive Rookie of the Year in 2018 and a three-time first-team All-Pro, signed a five-year deal worth $98.5 million. His $52.5 million in guaranteed money is tops for off-ball linebackers.

Warner was first-team All-Pro in 2020 and led the 49ers in tackles in each of his first three seasons. He signed a five-year deal worth $95.225 million, with a league-high average per year of $19.5 million.

The Bears might not see that kind of value for a weakside linebacker, which is a position that hasn’t generated the contract numbers of edge rushers or cornerbacks.

Only four off-ball linebackers make more than $15 million per year, and several lucrative contract extensions haven’t aged well. C.J. Mosley signed a five-year deal worth $85 million with the New York Jets in 2019, but he missed all but two games that season because of injury and opted out in 2020 because of the COVID-19 pandemic. The Minnesota Vikings gave Anthony Barr a $67.5 million extension in 2018 after three Pro Bowl seasons. He hasn’t made a Pro Bowl since and was limited to 13 games the past two seasons because of injury. Seattle released Bobby Wagner two years after he signed a then-record-setting deal that paid him $18 million annually.

Only five off-ball linebackers have been drafted in the top 10 since 2014, including Smith, who was drafted by the previous Bears front office.

“I think this is first an evaluation issue,” an agent said. “The Bears are not balking about paying a guy if they think he's a great player on top of the market.”

Poles has said there are elements of the Bears’ offer to Smith that are record breaking, but whether there are enough elements to get a deal done is uncertain.

What about the trade demand?

This is where things get interesting. The Bears could grant Smith permission to seek a trade, knowing it won’t be easy for a player representing himself.

“The Bears don't have the slightest concern whatsoever that he's talking to other teams,” one agent said. “There would always be a concern that another agent has a deal basically ready to go, on the backburner. But there's no way another team is gonna talk to an actual player who's under contract.”

That’s what the league sought to prevent by referencing its tampering rule in the memo sent Monday.

“I don't think he thought this through,” the agent continued. “If the Bears said, ‘Yes, OK, we give you permission to seek a trade,’ then what? What would typically happen is that an agent would call around, see if there's one party, and then if they find one, say ‘OK, if I can get a trade.’ Then the [new] team is going to want a long-term deal, as does the player. So then you’ve got to go into all these negotiations, and you might be negotiating with three teams, five teams.

“That’s a lot of work. He’s in camp right now. Is he going to do that between meetings?”

One agent said Smith drew a line in the sand with the trade demand.

“I just think Roquan made a big statement, and he's not coming back down unless he gets his contract,” the agent said. “So he’s got the Bears backed into a corner."

Will the Bears fine Smith for not practicing?

Smith avoided being fined $40,000 per day by showing up to camp on time and being at the Bears’ facility every day required of players during training camp.

Because he was taken off the PUP list, Chicago can fine Smith for not practicing. It’s unclear whether the Bears will go this route while trying to negotiate a deal.

“We expect all of our healthy players to practice,” Eberflus said.

What would an agent’s advice be to Smith?

One agent would have advised Smith to be “harsher” in his trade demand, but said overall, Smith hasn’t been hurting himself.

“If everything that's going on is what he's saying, we probably would've advised him to do what he's doing anyway,” the agent said. “I think he’s actually right on track with what he should do, because we're talking about a really, really good player. And if they're not even coming out with offers that are respectable -- we've been in that situation recently with teams, with some of our guys that deserve long-term deals and they feel disrespected.

“It’s like these guys get drafted, they do what you hope they’ll do, and then teams act shell-shocked when they ask for what they're worth.”

Another agent said the key is to play just enough to get to free agency while trying to avoid the franchise tag.

“I would just bad mouth the club and just say let’s get through these 17 games, there's no way they can franchise you,” the agent said. “They’re not going to pay you, that's obvious. So, you're 17 games away from the market.”