There's still time for the Portland Trail Blazers to sign Anfernee Simons to a contract extension. The league-wide deadline to ink fourth-year players still on their rookie contracts to an extension is October 18th, two days before Simons and the Blazers host the Sacramento Kings at Moda Center in the 2021-22 season opener.

But the powers that be didn't wait for Monday to come and go before leaking to The Athletic's Jason Quick what had long been obvious to anyone paying attention. Portland and Simons wouldn't come to terms on a new contract before the deadline, ensuring he'll hit the restricted free agent market next summer.

The writing was on the wall here dating back months, even once it became clear last season that Simons wouldn't breakout to the extent optimists believed he would. Simons still took meaningful strides in 2020-21, his third NBA season, especially as a shooter. He finally lived up to his pre-draft billing as a true marksman, shooting 51.4 percent on catch-and-shoot threes—third in the league, per NBA.com/stats—and connecting on 46 off-dribble triples, more than he made over the two previous seasons combined.

Simons shot a middling 33.6 percent on those pull-up tries, and 40.6 percent from two overall—the latter an easy career-low. He made little to no progress as a finisher at the rim and from floater range, also struggling to prove his bonafides as a secondary playmaker. Simons showed flashes of newfound comfort running pick-and-roll, but not near enough dynamism to play point guard full-time. His defensive improvement, especially late in the season, was notable, but more a reflection of how far behind Simons was on that end compared to typical rotation players than one he'll ultimately develop into a positive defender.

Simons enters 2021-22 entrenched in the Blazers' rotation. His trajectory from here, though, remains very much a question mark in both directions, the biggest reason why it never made sense for player nor team to seriously consider a contract extension as opposed to revisiting a possible deal in restricted free agency.

Portland will have the opportunity next summer to match any competing contract Simons signs. The Blazers will have the option of retaining Simons irrespective of price, and the more they're forced to pay him, the happier they should be. Simons has the best chance of any young player on his team to develop into a game-changer. If he thrives co-running the second unit with C.J. McCollum and starts putting his rare athleticism to regular use as a halfcourt penetrator and transition finisher, Portland will suddenly possess a new degree of roster flexibility—key as Damian Lillard's long-term future still hangs in the balance.

But the Blazers were never going to pay for that growth before Simons actually proved it beyond training camp, where his performance has been the talk of teammates and coaches. Likewise, Simons wasn't going to accept any extension offer befitting his current status as a marginal backup. His qualifying offer for next season is approximately $5.8 million. It would have been unprecedented for Simons to accept an annual salary that wasn't well into the eight figures, and made just as little sense for Portland to extend him such a contract considering his $11.8 million cap hold for summer 2022.

Larry Nance Jr. actually signed the cheapest rookie extension in the league over the last half decade, a bargain four-year, $44.8 million contract that declines in average annual value and expires in 2022-23. Rookie-scale extensions just aren't agreed to on terms that might mave made sense for both Simons and the Blazers. Both sides are better off taking the relative risk of restricted free agency, maximizing Simons' earning potential and mitigating Portland's downside of overpaying.

Here's hoping Simons plays well enough this season to make the decision on parameters of his next contract just as easy for he and the Blazers.