Chicago Bears running back David Montgomery will serve as one of the team’s captains in Sunday night’s showdown against the Green Bay Packers. Montgomery is a deserving choice to be a captain for the Bears’ biggest remaining game of 2021, as the third-year running back has been the heartbeat of the offense every time he’s on the field.

Montgomery’s 2021 season hasn’t gone exactly as planned, but he’s still been productive. He missed four games with a knee injury that occurred right as he began ascending into the NFL’s elite tier of running backs. And even though he hasn’t had a monster performance since his return in Week 9, he’s averaged more than four yards per carry in three of his last four games and has 134 carries for 566 yards and four scores on the year.

Still, for as good as Montgomery’s been over the last two seasons, it’s reasonable to wonder whether the Bears should invest big money in a contract extension at the end of next season (or sooner) to keep him in Chicago. According to Pro Football Focus, Montgomery isn’t even the highest-graded running back on the Bears. That distinction belongs to rookie Khalil Herbert, whose 82.1 is markedly better than Montgomery’s 76.4. Herbert was fantastic in relief of Montgomery during No. 32’s time out of the lineup, and he still has three years remaining on his rookie deal. You don’t have to be a salary cap expert to know it’s better if you can get cheap yet high-end production at running back; Herbert will be that guy for two years longer than Montgomery.

Montgomery’s contract situation becomes even more complicated when you start looking at what some of the highest-paid running backs make. Ezekiel Elliott signed a six-year, $90 million deal. Alvin Kamara inked a five-year, $75 million contract. McCaffrey? Four years, $64 million. Dalvin Cook is making almost $13 million per season, and Derrick Henry’s new contract pays him $50 million for four years.

Even if you don’t think Montgomery has an argument to be paid like that tier or players, which he probably doesn’t, the next cluster of contracts also appears prohibitive. Joe Mixon has a four-year, $48 million contract. Aaron Jones, who seems like a comparable player to Montgomery, is getting paid the same deal as Mixon. Nick Chubb signed a three-year, $36.6 million deal at the start of this season.

It may be more reasonable to think a fair deal for Montgomery is something like what Austin Ekeler signed: four years, $24.5 million. It kind of has to be, right? The Bears already set a precedent with running back contracts by doling out $17.25 million over three years for Tarik Cohen, who every Bears fan will agree has nowhere near the level of importance to the team that Montgomery does.

The Bears do have one thing working in their favor if they want to go against the grain and give big money to Montgomery: they have a four-to-five year window of a reasonable quarterback contract while Justin Fields is on his rookie deal. Unlike teams burdened by bloated quarterback contracts, the Bears will have some cap flexibility over the next couple of seasons (once contracts like Andy Dalton and Nick Foles are off the books). Giving Montgomery a nice pay raise won’t have as negative of an impact on the team’s ability to allocate resources to more important positions as it might if Fields was due for a contract consistent with a franchise quarterback.

But the harsh reality whenever a team is considering signing a running back to a big contract extension is that the long-term returns usually don’t pay well. The Dallas Cowboys’ decision to sign Elliott to a monster deal feels like it’ll be a regrettable one. Kamara is banged up, McCaffery barely plays. Cook is one hit away from the injured list, and Henry’s foot completely gave out. Jones and Chubb have battled injuries this year, and the Bears’ own investment in Cohen has been an absolute disaster. It feels like he’s never coming back from his ACL injury.

Montgomery is a stud who sets the tone on offense for the Bears. He’s just as talented as the running backs who’ve already broken the bank, but the track record of those running backs breaking down may prevent Montgomery from earning a massive payday in the Windy City.

A lot will depend on how the next five games go for the Bears offense. If Montgomery is a big factor in a late-season turnaround in a backfield led by Fields, there’s no logical reason why Ryan Pace (or whoever the general manager is this offseason) shouldn’t consider approaching Montgomery’s agent about a possible extension. The Bears don’t want to enter next year as a contract year for their starting running back. A career year means a more expensive contract or the dreaded franchise tag. We all know how that tends to go (see: Robinson, Allen.).

Even though the Bears are all but out of the 2021 playoff hunt, roster issues like this—whether Montgomery is a second-contract running back or not—become critical points of evaluation for the rest of the season. These games matter, even if it’s not the kind of ‘matter’ Bears fans care most about.

To sign Montgomery or not to sign Montgomery. That is the question. And it’s one Montgomery has a lot of control over, one carry at a time.