TORONTO – By midnight on Monday the Toronto Raptors will have to do what so far has been almost impossible to do: Make an accurate bet on how good Terrence Ross is or can be.

This is like guessing how big a room is in the pitch dark. Depending on which wall you starting sliding your hand down, you might end up with a very different idea.

The deadline to offer the No. 8 pick in the 2012 draft passes when the clock strikes 12. The Raptors have had some talks with Ross’ agent but as of Sunday night hadn’t made an offer.

He’s not an easy player to value properly. His day-to-day resume is a bit thin, but the potential remains and at his best he offers something that is essential in the modern NBA – an athletic, deep-shooting wing who can cover elite athletes on defence.

Ross is a dunk contest champion and shares the Raptors single-game scoring record of 51 points with Vince Carter. Two seasons ago he shot a more-than-respectable 41 per cent from the three-point line. He can, when moved, guard two or three different positions, and he can run like the wind.

But then there are moments when Ross plays likes he’s exhausted from staying up too late playing Call of Duty against some online pals in New Zealand, which may not even be a stretch.

His last two games — parts of them, anyway — tell the tale perfectly.

On Friday night against the Boston Celtics it was Ross who closed the door for Toronto, as he counted 13 of his 21 points in the fourth quarter, making full use of his 21 minutes of floor time. But as the Raptors improved to 3-0 on the season with an easy 106-87 win over the visiting Milwaukee Bucks Sunday, Ross was invisible, at least in the first half when he missed an open three, an open baseline jumper off an inbounds play and a runner he took without much conviction. Defensively he lost his man more than once as well.

“Consistency is the key on both ends of the floor, not just his offence but his defence,” said Raptors head coach Dwane Casey, who became the winningest coach in Raptors history with his 157th win, passing Sam Mitchell. “And that’s a huge question with him.”

It’s easy enough to suggest that Raptors general manager Masai Ujiri should show some tough love and let the deadline to sign Ross to a contract extension pass and let him prove his worth this season. Without an extension he’ll be a restricted free agent next summer. The Raptors would be able to match any offer he might get.

Let him earn it.

But even that is complicated.

If he has anything that even hints at a robust year he’ll be on the market in a summer when the NBA’s salary cap is expected to jump to more than $90 million from $70 million this year due to an influx of record TV revenues. All kinds of teams will have loads of money to spend and Ross could be the beneficiary.

Ross finally awoke early in the fourth quarter of Sunday’s contest with a trio of corner threes that helped blunt a brief Milwaukee surge. He snuck in for a lay-up off an inbounds play too and finished with 11 points on nine shots in 20 minutes. Defensively he was active covering the Bucks’ Michael Carter-Williams and helped force a couple of fourth-quarter turnovers.

That’s two straight games he’s come off the bench to be a deciding factor. Is that the start of something? Or is it an uptick before the inevitable slump that Ross has shown so many times before.

Looking around the league, players that fit that profile are hard to find and expensive when get identified.

Over the past two years Ross has shot 38.3 per cent from three and made an average of 153 triples each season. Only eight players topped those thresholds last season and they are some of the most lethal perimeter weapons in the NBA.

According to Basketball-Reference.com the list starts with Steph Curry and ends with Kyrie Irving. Wesley Matthews was on it and he signed a four-year deal worth $70 million with the Dallas Mavericks this past summer while he was out with a torn Achilles tendon. Danny Green of the San Antonio Spurs was on it and he got a four-year deal worth $40 million this past summer, one that many thought had a heavy hometown discount. The L.A. Clippers have J.J. Reddick under contract at four-years and $27 million.

Are Raptors fans ready for a four-year deal for Terrence Ross that pays him $40 million? It seems crazy to contemplate, but $10 million is the new $6 million in the NBA, and I’d bet the Raptors would sign Ross for $6 million a year in a heartbeat. There will be a lot of crazy deals getting signed in the next two years that will seem less crazy as the salary cap climbs. The Raptors might simply be getting ahead of the curve.

Signing the right player to the right extension can be a bonanza for a team. The Raptors looked profligate when former general manager Bryan Colangelo signed DeMar DeRozan to a four-year deal worth $38 million on the eve of the 2012-13 season. It turned into a tidy, club-friendly contract almost from the moment the extension kicked in for the following season.

There are some good arguments to believe getting a deal done for Ross would make smart business. For most of his time in Toronto Ross had had to live off the offensive scraps left when DeRozan, Kyle Lowry, Rudy Gay, Greivis Vasquez and Lou Williams have finished chewing through the first course.

Last season alone DeRozan, Lowry, Vasquez and Williams combined to take nearly 52 shots a game. Their should be more meat on the bone for Ross this season and in a primarily second-unit role playing alongside a distributor like Cory Joseph, Ross should be able to find his offence more consistently than waiting for whatever was left over at the starter’s table.

“I feel comfortable in the role, it helps me relax and see what I need to do. I like it,” Ross said after the game. He’s also feeling better after having off-season ankle surgery to remove bone spurs.

“It feels good, last year it was difficult playing on defence, trying to move and cut,” he said. “I don’t want to use that as an excuse, but it definitely feels a lot better. This year I have a lot more mobility and I feel like it helps.”

He’s got a supporter in Vasquez, who was traded to the Bucks in the off-season in part to give more room for Ross to breathe. Ross will need to adjust to coming off the bench, but there are opportunities there.

“You have to be tough mentally [coming off the bench],” said Vasquez who scored nine points on seven shots while adding four assists Sunday. “Obviously you want to start – what player doesn’t want to start in this league? But you you have to have a great amount of confidence in yourself and what you can do.

“But T-Ross, is going to do a great job. Whether it’s here or somewhere else. He just has to be professional, play hard, play good D and hit shots, and that’s what he does.”

Which isn’t to say that Ross has proven that he deserves a contract extension that pays him more than $10 million a year, only that it’s not crazy that he could eventually become a reliable floor stretcher and defender. And in the NBA contracts don’t always reflect current worth, but instead reflect perceived potential and timing.

“We’re still talking about it, we’ll see what happens, but I’m not sweating it,” Ross said of his extension, acknowledging that the market conditions should be in his favour next summer. “It would be nice to get one, but if it doesn’t work out, it doesn’t work out. It will all work out for the best.”

For Ross the potential has always been evident, and his timing is impeccable.