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Is Now The Time For The Blazers To Extend Meyers Leonard?

October is the Trail Blazers' last chance to offer Meyers Leonard a contract extension before he slips away into restricted free agency next summer. Will they make a deal?

Is Meyers Leonard worth "John Henson money" to the Blazers?
Is Meyers Leonard worth "John Henson money" to the Blazers?
Jaime Valdez-USA TODAY Sports

Three years. For the average NBA player, that's the entire window of opportunity you get to prove your self-worth as a professional - it's just three years. That's it. You play a year or two in college, you declare for the draft at 20, you play until you're 23, and that's when your team reaches a crucial inflection point to decide upon your future. At that moment, you're either in or you're out.

This is baked into the NBA's collective bargaining agreement. The way the CBA works, most first-round draft picks are signed to rookie-scale contracts of four years in length, and toward the end of that four-year period, there's a brief window during the final summer when teams decide whether to extend those rookie deals or not. The fortunate few who get extensions strike it filthy rich; those who don't risk falling into the cesspool of restricted free agency, which is a rigged game that discourages GMs from pursuing other teams' guys. Once you hit RFA status, you're in a difficult spot with no leverage and no guaranteed future. Just ask Tristan Thompson in Cleveland.

For players to avoid RFA, they've got to agree to extended deals over the summer. The extension period begins immediately after the end of the July free agency moratorium (this year it was July 8) and concludes at the end of October. This year, the league pushed the deadline back to Nov. 2 because Oct. 31 falls on a Saturday, but no matter. We're still talking about less than four months of negotiating time for players and their teams to iron out massively important decisions about the staggering, life-changing amounts of money they stand to earn. It's a pressure cooker, for sure.

Only a select few guys walk away with extensions during the summer. In most cases, it's obvious who's getting a deal and who isn't. Anthony Davis, the undisputed best rookie-scale contract guy in the league today, sat down with the Pelicans and hammered out a five-year, $145 million agreement right at midnight on the first day of free agency. He's an obvious max guy, so New Orleans just gave him the money right away. Done deal. In Portland, Damian Lillard was a similarly clear decision, so Neil Olshey was quick to offer his franchise player five years and $120 million, which Dame accepted. Meanwhile, on the other end of the spectrum, Moe Harkless is also entering the fourth year of his rookie deal, but it's pretty certain Olshey's not interested in extending a bench guy who's still fairly unproven at the pro level. Harkless is bound for RFA next July.

The only real question marks lie in the middle. The players we get to debate in October are the in-between cases - the fourth-year guys who aren't superstars getting nine-figure deals, but they are worthwhile NBA players that their teams are motivated to keep. With these middle-class guys, the question is whether that four months of negotiating time is enough for the two sides to sit down and agree on an acceptable salary.

That being the case, it's time to debate that question as it pertains to Meyers Leonard.

Leonard isn't in the same class as Davis or Lillard, obviously, but it's starting to look like he's the kind of player that's worth a multi-year contract extension in the tens of millions. He's a 7-foot-1 big man who's adept both guarding the paint defensively and stretching the floor offensively with his monster 3-point shot - even in today's shooting-heavy league, Leonard is a rare commodity. He's worth money.

The difficult question, though, is how much. Leonard is still only 23 and has still played only 2,408 minutes in his entire NBA career - for comparison's sake, 43 players in the NBA put in more time than that last season alone, including Portland's own Lillard and Aldridge. How do you arrive at a precise dollar figure for a guy who's so young and so unproven?

The answer is that to get a deal done, someone is going to have to take a significant gamble. Who will it be - Olshey and the Blazers, shelling out a boatload of money for a guy they aren't entirely sure can keep producing? Or Leonard, settling now for a likely modest paycheck when he could bet on himself and make far, far more money in free agency next summer?

There are a whole lot of questions here. Let's go through them.

1. Is Leonard's performance sustainable?

You've already read this stuff a million times this summer, no doubt, so I won't go into it in terribly much depth. But for a quick refresher course: Leonard was a dazzling offensive player last year, shooting 51.0 percent from the field and 42.0 percent from 3-point range, and he was underratedly fantastic on the defensive end as well. According to SportVU, data, he held opposing players around the rim to just 42.3 percent shooting, one of the lowest marks in the league.

He also only played 15.4 minutes a night, which made it easy to call his amazing performance into question. Sure, Leonard was great, but can he keep it up when he's not hiding in LaMarcus Aldridge's shadow anymore? How much of last year's production will he sustain when he's got a far bigger role?

The more I watch Leonard this preseason, the more I feel like the kid's for real. It's looking like last year wasn't "small sample size theater" - it was the legitimate product of a style of play that's confoundingly difficult for opposing teams to combat. Leonard isn't just a shooter prone to hot streaks. He's also a matchup nightmare.

Consider this example:

(Disclaimer: Yes, I'm about to analyze a few plays from preseason basketball games. Let me just preempt the angry comments and tweets now: I am aware that preseason games mean nothing. You don't have to lecture me on that, I promise. But I still think little snippets of exhibition action here and there can be instructive about how the team's style of play will look during the regular season. Sue me!)

Anyway, the above clip is a great illustration of what makes Leonard so deadly for opposing defenses. Leonard is two things offensively - he's a great pick-setter and a highly efficient shooter when he's got open space to operate. So Leonard creates opportunities for himself by doing what he does best - picking, picking and picking again until it results in an open shot opportunity.

Portland's Tim Frazier starts out this play with Utah's Trey Burke guarding him, and Leonard tries to disrupt Burke - after firing a pass over to Pat Connaughton on the wing, Leonard attempts a pindown screen on Burke, who scampers quickly around him. Frazier gets the ball back at the top of the key, and Leonard picks again - this time, forcing Burke and Leonard's man, Derrick Favors, to make a tough decision about guarding the pick-and-roll. Burke ends up going over the screen, and Favors drops back to guard against Frazier driving to the rim. Neither player makes an effort to close out on Leonard at the 3-point line, so Leonard lets it fly. Money.

This play illustrates Leonard's perseverance as a screen-setter - if the first attempt doesn't work, he's happy to try again, even if it ends up burning a lot of the shot clock. Getting Leonard some open space to work with is worth the effort, as Leonard shot 14.3 percent from 3 last year when a defender was within 4 feet of him and 43.8 percent when one wasn't.

The thing is, the Blazers often don't even need to run plays to get Leonard open looks. Sometimes, the opportunities just show up because defenses aren't ready for him:

There's no reason that this transition play should turn into an open 3-pointer for Meyers Leonard. You'll note that of the 10 guys on the floor here, Leonard is the last one to get down the court in transition. But he's still open, because the Jazz fall asleep on guarding the 3-point line as Leonard lumbers his way up there. Utah's attention is focused on C.J. McCollum, who's attacking the basket with a head full of steam - Favors, who's supposed to be guarding Leonard, instead opts to collapse into the paint against C.J. rather than stick to his man. By the time he realizes Leonard is spotting up for 3, it's far too late to do anything about it. He leaps out to the perimeter to no avail as Leonard drains the jumper.

Then again, how is anyone supposed to stop that shot? Leonard is 7-foot-1, meaning he can easily score over undersized power forwards, but whenever he's matched up against a bigger guy like Favors, that player ends up being unable or unwilling to close out to the 3-point line and take away his outside jump shot. Who in the NBA has both the size and the quickness needed to contest a shot that deadly against a guy that big? A couple of names from around the league come to mind - Serge Ibaka is one, plus the aforementioned Davis - but there aren't many.

Unsurprisingly, Leonard's ability to hit 3s in a variety of situations translates to devastating efficiency. According to Synergy Sports, Leonard had 59 plays last year as a pick-and-roll man, and he averaged 1.32 points per possession - among 125 guys in the league with 50 attempts or more, he ranked sixth. In transition, he had 31 attempts, and he was sixth out of 343 (!!!) guys with 25 opportunities or more. This isn't exactly college-level calculus - it's the "three points is more than two" thing. Leonard's shooting is a monster difference-maker.

Leonard has been pretty good defensively this fall as well. Here's a nice clip of him taking on Favors and the Jazz:

There's nothing sensational or eye-catching about Leonard defensively - it's not an athleticism thing, really. He doesn't jump out of the gym or cover ground with extraordinary quickness. But what Leonard does do quite nicely is position himself in such a way that he can help teammates defensively without giving up ground to his primary man. Watch Leonard on this possession. Favors is the guy he's assigned to guard, but Leonard ventures away a couple of times to freelance. First he takes one or two steps to his right to protect against a potential drive from Elijah Millsap; next, he goes one or two steps left to cut off Alec Burks. He then recovers nicely to the middle of the floor and contests beautifully as Favors attempts to go to the rim.

We still have limited information to work with here - don't get me wrong. But at the moment, it would appear that Leonard is capable of continuing the fine work he's done so far. He's not just a kid with fluky good stats. He's a player who's demonstrated, time and time again, that he's got skills that will carry over for years to come.

2. If you're the Blazers, do you want to extend Leonard now?

OK. Here's where things get difficult. Even if you agree with all of the above, how much do you really think the Blazers are comfortable spending on a guy with less than 2,500 total NBA minutes under his belt?

There's no doubt that, at least according to everything Olshey has publicly said on the record, Leonard fits into the vision that the Blazers' GM has for the team's future. To wit: Olshey told the Washington Post in August that his current plan is to build around guys who "want to be in Portland." He also told Grantland that he wants players who are "on the same career arc as Damian Lillard."

Both of those statements seem to fit Leonard well. He obviously loves it here - Leonard got married in Portland, bought a house in Portland and he even has a poster of the city's bridges. As for the career arc thing, they were taken in the same draft, five picks apart, so you tell me.

To all outward appearances, Leonard fits the profile of a longtime Blazer, but it begins to get tricky when you start talking about actual dollar figures. Reality check: Young big men are extremely expensive these days. If you're a 7-foot dude who can play basketball even slightly competently, you get paid handsomely. Look at the extensions that are going around already - Jonas Valanciunas got four years and $64 million from Toronto. John Henson got four years and $44 million from Milwaukee. Festus Ezeli hasn't signed anything yet in Golden State, but there are Warriors bloggers casually tossing around numbers like $10 million a year, and we're talking about a backup who plays 13 minutes a night and is just barely capable of catching a basketball.

Given all that, how much do you think Leonard can demand? He's at least as valuable a player as Festus Ezeli, isn't he? Shouldn't he be asking for $10 million or $11 million too? And if you're Olshey, are you really prepared to shell out that kind of cash right here, right now?

3. If you're Leonard, do you take the money right away?

Now, let's look at this from Leonard's perspective. Let's say - and I'm not predicting this necessarily, but just for the sake of argument let's toss it out there - that Olshey offers Leonard an extension this month that's somewhere in the Ezeli-Henson range. Say he gives Leonard $40 million right now to lock him up as a long-term Blazer. If you're Leonard, are you tempted?

I cannot emphasize strongly enough that no matter who you are, $40 million is a life-changing amount of money. It must take incredible courage to look a man in the eye and say, "I appreciate your offer of $40 million, but no, thank you." Even if rationally that's the right decision, it's got to be an incredibly difficult choice to make. (For the record, I have never been in this situation myself. I'm just guessing here.)

Still, though, there's a name for this phenomenon, right? They call it "betting on yourself," I believe, and Leonard has a lot to bet on. If he thinks he can sustain his stellar shooting and solid paint defense for another season, he might put himself in position for a far bigger payday next summer. We've seen this happen before. Jimmy Butler was in an extension standoff with the Bulls at this time last year; he ended up waiting, playing out the season, winning Most Improved Player and locking in a max contract worth $95 million. Khris Middleton in Milwaukee was similarly unable to work out an extension in October 2014; he had a monster breakout season and ended up getting $70 million to stay with the Bucks.

There are a million ways that Leonard could fail to become the next breakout star like Butler or Middleton. What if he gets hurt? What if he wilts under the pressure of playing more minutes? What if his performance this year is only OK, and he gets overshadowed by another youngster in Portland like, say, Noah Vonleh? What if, what if, what if?

Then again, what if Leonard is awesome this season? The last thing he wants to do is accept $40 million now and realize later he could have banked $70 mil. That's the risk he's running if he pushes for an extension now.

4. Ultimately, what happens?

In the end, this is a perplexing case for the parties on both sides. The Blazers must be tempted to extend Leonard, as he's a good player who could fit nicely with Lillard as part of the team's nucleus long-term; Leonard must be tempted to sign too, as he's got a chance to grab a whole lot of guaranteed money.

In the end, though? My guess is nothing happens this October. There's probably a certain level of mutual interest, but this may just be too volatile a situation for the two sides to agree on a precise number. To me, the only outcome that makes sense is the two sides haggle a bit, they table the conversation once the season starts, and they wait until next July to talk about a final decision.

I'd love to hear arguments to the contrary. Do you think Leonard and the Blazers get a deal done now and carve out a long-term partnership? Share your thoughts in the comments below.