With The Season Over, Attention Turns To The Draft, Trades And Free Agency

by Casey Holdahl
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While no one was happy with how the 2021-22 season played out for the Trail Blazers, at least it’s over. Portland scuffled through the first half of the season due in large part to injuries and then full on struggled in the second half after executing trades to improve the team in the future at the expense of the present. It might have been the best approach for the long term prospect of the organization, but it still didn’t sit especially well with leadership nor the players.

“I still feel uncomfortable about it,” said interim general manager Joe Cronin of the end to Portland’s season, which saw the team win just twice in their last 22 games. “We have a really competitive group, we didn’t want to lose ball games. Sometimes it necessary, sometimes you have to go with your youth movement, but our goal all along was for this to not be an extended period of losing.”

While a healthy Damian Lillard, who missed the last three and a half months after undergoing abdominal surgery but is expected to be completely recovered by the start of the 2022-23 season, is enough to assure a competitive team, the goal is to be much better than just competitive, and in relatively short order.

“We had to take a step backwards in order to move forward,” said Cronin. “We’ve positioned ourselves to where I think we’ve got some great opportunities. We have a really intriguing core: Damian Lillard, Anfernee Simons, Josh Hart, Jusuf Nurkic, Nassir Little, Justise Winslow. Potentially two lottery picks, numerous cap exceptions, a bunch of cap flexibility. We are determined to get better, to be competitive as quickly as possible and we’re super confident in our ability to do that.”

In order to acquire the talent required to get better, and quickly at that, Cronin and his staff will need to have success in the three areas this offseason in order to turn things around quickly. Let’s look at those three areas.


The first order of business is to prepare for the upcoming NBA Draft, which will be held on Thursday, June 23 at Barclays Center in Brooklyn. The Trail Blazers will have at least one lottery pick (their own) and potentially another if the New Orleans Pelicans miss the playoffs (the nine-seed Pelicans will have to beat the 10-seed Spurs on Wednesday in their first “play-in game” and then the loser of seven-seed Timberwolves vs. eight-seed Clippers in order to make the postseason).

And while the probabilities say Portland’s own pick will be sixth and the New Orleans pick, should they get it, will be 11th, the actual order will be determined by the 2022 Draft Lottery, which will be held May 17 in Chicago.

But while they won’t know which picks they own for at least a month, the preparation is already well underway.

“We’re still evaluating,” said Cronin. “We’ve got the draft combine in a little over a month where we get some of the information we don’t have access to, the medicals, the interviews where you’re building your entire book on the players. From a straight basketball perspective, I think it’s a solid draft. I’ve been focusing heavily on the lottery with having potentially two lottery picks and the depth of the talent is intriguing to me right now.”

Of course, selecting a player in the draft isn’t the only way to come away with talent at the draft. According to Cronin, the goal is to “maximize the pick,” which could just as easily mean using the pick as an asset in a trade as it could using the pick on a draft-eligible player. And considering that the goal seems to be to reload rather than rebuild, using the pick (or picks) to acquire veteran talent might be the direction the team goes.

“I’m going to spend the next two, three, four weeks diving into the game film and really evaluating this draft and particularly assessing value to what that pick is,” said Cronin. “So then you compare that to what’s available in the marketplace and then you make a decision. If we decide the player at that pick is much more valuable than what we can get in the marketplace, we do that direction. If it’s the opposite, we go the other direction.

“I don’t want to play both sides. We want to win, we want to be really competitive next year and I think we’re all aware you’re more likely to win with veteran players than young players, so that will definitely be a part of our decision-making process.”


Which brings us to the prospect of trades this offseason. Cronin and his staff pulled off three significant trades prior to the 2022 NBA trade deadline that netted both players -- Josh Hart, Justise Winslow, Joe Ingles, Eric Bledsoe, Keon Johnson, Didi Louzada and Elijah Hughes -- and trade assets -- the protected first-round pick from New Orleans and three trade exceptions -- all of which can be used in trades this offseason.

“I would say the biggest challenge is getting the right amount of talent,” said Cronin. “I like our talent base; we need more. It’s hard getting great players in this league, whether it’s through the draft, through trade. In trades it takes two to tango, you need that trade partner. I hope that we have the assets and the cap flexibility -- exceptions, contracts -- to get that done, but getting that high-end talent is the biggest challenge.”

Just how valuable those assets will be in terms of putting together a potential trade is unknowable, but simply having some flexibility going into the offseason due to owning draft picks -- Portland hasn’t made their own first-round draft selection since taking Nassir Little with the 25th pick of the 2019 Draft -- and getting a number of long term contracts off the books should help facilitate deals should the right player become available.

“Every team in this league has players they covet but if they’re not attainable or if you don’t have the right assets or if they’re just simply not on the market, yeah, you have to wait,” said Cronin. “So sometimes it takes time for those opportunities to present themselves, but I also think we’re in a place where we don’t need to necessarily hit a home run right out of the gate in order to be competitive.”


The last piece of the offseason puzzle is free agency, which starts the first week of July. The Trail Blazers have not traditionally been a team that has had much success when it comes to acquiring free agents, especially the highly sought after free agents, but with a relatively new front office, a former All-Star player as head coach and buy-in from the franchise player, they just might give the free agent route another shot.

“It’s a generic plan where we’re going to be united as a group and we’re going to be ourselves and we’re going to be confident in that room,” said Cronin. “We don’t have a plan inasmuch as a power point presentation or some sort of recruiting pitch, yet, but it’s more Chauncey, Damian and I in a room telling stories about this organization and pitching players on things we believe in, how they can come in and help us achieve these goals.”

While the Trail Blazers could conceivably clear significant cap space, it would require waiving and/or not re-signing a number of players Cronin has described as parts of Portland’s “core.” Given that, it seems more likely that Portland will operate as a team over the salary cap but under the tax, which would allow them to use the non-taxpayer midlevel exemption, which is projected to come in at a little over $10 million per season, and the biannual exception, projected at around $4 million. That’s not enough to sign All-Star free agents -- there aren’t many, if any, of those hitting the market this offseason anyway -- but is enough to sign a solid rotation player, at least if the pitch is right.

But Portland’s big signings this offseason will likely revolve around trying to come to agreements with current players who are hitting free agency. And while there are limits to what a team can say about their own free agents, and negotiations cannot begin, even for players currently on your roster, until after the July moratorium, one gets the sense holding on to homegrown talent is an important part of their offseason plan.

First, there’s Jusuf Nurkic, who will be an unrestricted free agent this offseason, though Portland owns his “bird rights,” which allows the team to re-sign the player despite not having the requisite cap space.

“We are big fans of Jusuf Nurkic,” said Cronin. “I think he had a career year this year. Every year we’ve seen a significant amount of growth from him and expect that to continue. He’s only 27 years old, he’s just scratching the surface of his prime and I think he’s the type of player we would definitely want to build around.”

Then there’s Anfernee Simons, who will be a restricted free agent, meaning the Trail Blazers have the right to match any contract offered by another team. And there will be interest considering he’s not yet 23 years old and is coming off a season in which he averaged 17.3 points on 44 percent shooting from the field and 41 percent shooting from three, 3.9 assists and 2.6 rebounds in 29.5 minutes per game as one of the NBA most improved players.

“I have a sense, I think it will be strong,” said Cronin of Simons’ value as a free agent this offseason. “I think the league thinks super highly of him, as do we, and I’m sure he’ll have a lot of calls on July 1 and a lot of invites to meetings.”

But between the leap that Simons, who Portland selected with the 24th overall pick of the 2018 Draft, made this season under first year head coach Chauncey Billups, and the team trading away both CJ McCollum and Norman Powell, it seems likely that the Trail Blazers will do whatever they can to keep the 2021 NBA Dunk Champion in Rip City for the foreseeable future.

“My goal would be to be proactive,” said Cronin on recruiting Simons. “I think we have a really good relationship with Anfernee and his agency and I would hope that, once we’re allowed to start talking, that we can come to an agreement that makes sense for both sides.”


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