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What Should The Portland Trail Blazers Do With Their Impending Free Agents?

There's a lot of optimism about the Blazers landing a big name like Hassan Whiteside this summer, but the team's own impending free agents - Meyers Leonard, Allen Crabbe, Moe Harkless and Gerald Henderson - are important as well. What to do?

How much longer will these two be together?
How much longer will these two be together?
Thomas B. Shea-USA TODAY Sports

Coming off a surprisingly strong 44-win season, and with a young roster that ostensibly has noplace to go but up, up, up, it makes sense for the Trail Blazers and their fans to think big this summer in free agency. Maybe not big big as in Kevin Durant - especially given how well the Thunder fared in the Western Conference playoffs, it's hard to imagine KD leaving Oklahoma City this summer, especially not for a weaker team - but big. Names that may have seemed unattainable a few months ago might now seem kinda sorta within the Blazers' reach. Think Al Horford. Think Hassan Whiteside. Think ambitiously, Portland - you've earned it.

Having said all of that, there's also something to be said for keeping the Blazers' front office focused in the internal direction a little bit. There are a lot of tempting names out there on the open market, but you could argue that it's even more important for Neil Olshey and his braintrust to keep the talent they already have under contract.

Consider this: On the 2015-16 Blazers, only 47 percent of total player-minutes went to players who had already been with the team the previous season. According to basketball-reference data, that was the third-lowest continuity percentage in the league, leading only the hapless Lakers and Knicks. Building a successful culture is difficult in the NBA without continuity - your players don't get a chance to develop together and strengthen their chemistry with one another. Every season feels like a rebuilding season.

The Blazers, though, just won 44 games and a playoff round. They shouldn't have to rebuild anymore - now's their time to build. That means they should probably take a long, hard look at retaining their key guys who are heading for free agency this summer - especially those who are young, still improving and still under some degree of contractual control. You want to get a Horford or a Whiteside, sure. But let's first look at the Blazers' most basic building blocks.

For simplicity's sake, let's keep this to the Blazers' four main free agents. Brian Roberts was a serviceable backup this season but that's about it. Cliff Alexander and Luis Montero are non-guaranteed guys whose futures are very much in doubt. Chris Kaman - I love you, man, but I think your time here is up.

Here are Portland's "big four" and the outlook on each:

Allen Crabbe

His contract situation: As a second-round draft pick in 2013, Crabbe arrived in Portland on a three-year contract, which means he's up this summer. Crabbe, who made just under $950,000 this past season, is now headed for restricted free agency, where he will likely command many, many times that figure. The Blazers can keep him if they're willing to pay up, but the price might be steep.

His role in Portland: An interesting question, isn't it? The thing about Crabbe is that despite only having 17 career starts to his name as a Blazer, he could well make the case that he's good enough to crack the starting five on a dozen NBA teams right now. He was the third-leading scorer on a playoff team at 10.3 points per game, he shot over 39 percent from long distance and he's becoming more serviceable as a defender each year. In Portland, though, he seems destined to stay in more of a sixth-man role for the time being. It's not that Crabbe isn't talented - he definitely is - but his abilities as a shooter and scorer overlap a bit too much with what Damian Lillard and CJ McCollum already do, which is why the size and defensive acumen of an Al-Farouq Aminu are a better fit at the three-spot in Portland's starting lineup.

So if Crabbe's job is to be a super-skilled bench scoring specialist, that raises the big question - how much is that role worth?

What he'll be worth: Ask around about Crabbe's value in free agency this summer, and the numbers you hear back have eight digits, not seven. This sounds crazy, but put in perspective - first off, Crabbe is a promising 24-year-old player who keeps getting better, and second, the value of a dollar is changing rapidly in the modern NBA. The salary cap is increasing from approximately $67 million this past year to $89 million in 2016-17, which means every new contract will be about 133 percent of what it used to be. If you think Crabbe is a $9 million player in the old system, he's a $12 million guy now. In my opinion, he is and he is.

What should the Blazers do? That $12 million might sound steep, but the Blazers have a ton of cap space this summer, and re-signing key youngsters like Crabbe is likely to be the main thing they use that space on. Blazers writer Erik Gundersen (who, by the way, is a stellar hoops scribe and I wish him the best of luck with whatever the future brings) went so far as to say Crabbe is the most important of the team's restricted guys to bring back this summer, ranking him above the other guys you see below. I'm not sure if I agree, but I do think Crabbe is important to the team's long-term plans, and I think the Blazers have to profess their loyalty to the guy and match any offer that isn't completely ludicrous. Assuming no GM this summer goes bonkers and offers Crabbe $18 million a year or somesuch, I'd expect him back in Portland next year.

Maurice Harkless

His contract situation: Harkless was picked just outside the lottery in 2012; he closed out his four-year rookie contract in Portland this year. He made just under $2.9 million during his first season as a Blazer. Like Crabbe, he's now headed for restricted free agency, and like Crabbe, he can expect a hefty raise.

His role in Portland: It's a tricky question because we still haven't seen Terry Stotts give a consistent answer for any prolonged stretch of time yet. Harkless' per-game minute averages by month, from November to April of this past season, were 19.7, 15.5, 13.9, 19.4, 19.7 and 28.7. For a significant chunk of the season - like, from Thanksgiving to Groundhog Day - Harkless was picking up scraps of playing time off the end of the bench; then, late in the season when Stotts began to give up on Noah Vonleh, he was suddenly slotting Harkless in as his starting power forward.

Long-term, I think Harkless' destiny lies somewhere in between those two extremes. He's a skilled enough player to get major minutes for a good team, but I'm not sure how long he'll last as a starting four in the NBA. That post-Vonleh lineup with Harkless starting was arguably the best unit Portland played all season, but is it really a solution moving forward? Harkless is a bit too small to muscle up with real NBA bigs, and he's not quite enough of a shooter to be lethal from the perimeter. He's a weird in-betweener, and his role, in Portland or elsewhere, still isn't well defined.

What he'll be worth: For the above stated reasons, it's tough to say. I think somewhere in the $8 million to $10 million range is probably reasonable. In 2017 terms, that means he's a mid-level guy - a solid rotation player, not necessarily worth star money.

What should the Blazers do? Harkless is a nice player, and keeping him around isn't a bad idea by any means. I don't, however, see him as the Blazers' top priority. Keeping Crabbe is a near-must, and the other two guys below will also command a decent chunk of Neil Olshey's cap space if retained. The best strategy with Harkless is probably to wait and see. When free agency opens on July 1, Olshey will probably start by chasing bigger fish; if he doesn't land one, he'll probably have Harkless as a fall-back option.

Keep in mind that the grace period to match a restricted guy's offer sheet is longer now - if Harkless signs with another team, the Blazers have 72 hours to respond and not 48. That's a lot of time. Free agency moves quickly, and 72 hours is generally enough time to watch the dust settle on all the major free agents and evaluate your options from there. Stay tuned with Harkless; he's not Plan A, but he could be a plan.

Gerald Henderson

His contract situation: Henderson re-signed with the Charlotte then-Bobcats back in the summer of 2013 for three years and $18 million. He played out the final year of that contract in Portland this year, making $6 million; he's now an unrestricted free agent for the first time.

His role in Portland: Henderson was a good fit with the Blazers this year, though he was hardly an irreplaceable guy. He was basically exactly what Neil Olshey thought he would be - a solid, dependable third guard, doing a little bit of everything. He defended, he hit open shots, he moved well around screens, he made smart decisions. He even played bigger than his size on some occasions, shifting to the three and even the four and showing some post-up chops and some glass-eating. Henderson was solid. If he returned next fall, he would most likely remain solid. At the same time, solid third guards kinda grow on trees, and if the Blazers don't bring Henderson back, they will surely find a way to survive without him.

What he'll be worth: Henderson was a $6 million guy three summers ago, when he was 25, and he's pretty much the same steady player now at 28, so I see no reason his value would change much. Adjusting that figure for the modern-day cap, does $9 million a year sound reasonable?

What should the Blazers do? I suspect the Blazers' plan with Henderson will be pretty similar to their plan with Harkless. They like Henderson, because why wouldn't they? But he's hardly their top priority. The most reasonable course of action for the Blazers is to play the field, talk to a few free agents who might give them an upgrade, keep an eye on their cap sheet and then consider coming back to Henderson if they still have the money and the positional need come July 10 or so. I'd say he's an even 50-50 bet to be back in Portland next year.

Meyers Leonard

His contract situation: Leonard was a lottery pick in the 2012 draft (four spots ahead of Harkless, actually). He played his entire four-year rookie deal in Portland, earning just under $3.1 million this past year. Like the other rookie-scale guys above him, he's gonna get plenty more than that now.

His role in Portland: I swear, I didn't mean to put Leonard at the end of this list - the order is simply alphabetical - but it's fitting that he gets saved for last, because he's really the main event here. No Blazer sparks more contentious debates among fans than Meyers Leonard. What is Meyers' role on this Blazer team, anyway?

When the season began back in October, the expectation was that Leonard would start at power forward and absorb the lion's share of the minutes that LaMarcus Aldridge left behind when he departed last summer. Things began that way, anyway; they didn't continue. Leonard got injured in November, gave Noah Vonleh his starting job and, for whatever reason, failed to earn it back.

I have no idea what to say about Leonard's role now. Why didn't he play more minutes this year? His 21.9 per game were of course a career high, but nothing like the increased workloads that McCollum and Crabbe got on the new-look Blazers. The thing about Leonard, I'd say, is that he's a difficult player to simply plug and play as part of your rotation. His size and skill set are so unique that you can't just sub him in for someone like Mason Plumlee or Ed Davis and keep rolling - his presence dramatically alters the makeup of your team. Anytime you insert a 7-footer who can make 40 percent of his 3s, the whole game plan changes. The Blazers never quite found a rhythm this year working Leonard in and out of games effectively, and the whole team suffered a bit as a result.

The Blazers this summer have an assignment, and it's this - be decisive about Meyers Leonard. Choose a course of action and stick with it. Either re-sign the guy and be clear about your commitment to play him big minutes in a system that uses him effectively, or don't. Let him walk. Pick one plan or the other and execute it. Another year of being wishy-washy about Leonard's role - or, god forbid, another four - is just a waste of everyone's time.

What he'll be worth: Another big question. What value has he actually demonstrated on the basketball court? Probably somewhere in the neighborhood of $10 million or $11 million. What will he actually command on the open market this summer? A lot more than that, in all likelihood. A 7-footer who can shoot like Leonard is always tantalizing, and all it takes is one eager GM in a pool of deep-pocketed GMs to overpay him. Someone will toss $15 million a year at Meyers Leonard. I don't know who, but someone. Book it.

What should the Blazers do? The biggest question of all. This is the one we've all been fighting about for months - in Twitter exchanges, at bars, in the 300 sections of the Moda Center, you name it. Everyone's got a take. I suppose it's my duty, at this time, to provide mine.

Me personally? I still believe in Meyers. I understand that he's still not fully proven as a big-money NBA player, but he's a gamble that I want the Blazers to take. I said above that Gerald Henderson is good but replaceable; there are a lot of third guards in the NBA who can give you mid-level skills for mid-level money and do a lot of things reasonably well. There are not, however, a lot of 7-footers with Leonard's jump shot - and bear in mind that besides that, Leonard has also blossomed into a pretty decent post defender.

The two things everyone wants from their big men in 2016 are floor spacing and rim protection; Leonard is the rare guy who offers a tantalizing chance to get both in one. He might not be perfect, but he's got more untapped upside than anyone on the Blazers' roster today, with the possible exception of the aforementioned Mr. Vonleh.

One of the ways to go from good to great in the NBA is not to land a superstar player on the trade market or in free agency, but to develop a guy in-house and help him reach the next level. Seemingly every champion has a breakout guy like that - look at Draymond Green in Golden State, or Danny Green in San Antonio before him. What if Meyers Leonard is the Blazers' next breakout player? I would argue that still, even after four years, they haven't tried hard enough to find out. Remember - even with a bigger role this season, he still only played 21.9 minutes per game!

At this stage in their long-term growth, the Blazers are already a competitive team, but the next step for them will be to look for upside plays that can launch them from 44 wins to that seriously competitive upper echelon of the Western Conference. There's a good chance that somewhere within this year's Blazer free agent class - maybe with Leonard, maybe with Crabbe or Harkless - there's a guy whose continued growth can help them reach the top. They'll never know unless they pay up for the chance to find out.