• It’s that time of the year again where we put on our general manager hats and do two things.

    1) We predict what the contracts are going to be – and
    2) We rank the contracts accordingly

    The idea is that if a general manager wanted to rank who they were targeting, excluding stuff like the salary cap and fit and the arc of the franchise, they could take the year off and just use this list.

    As contracts get agreed to we’ll come back to this article and provide a letter grade for each deal. Hopefully your team will pick from the top and not from the middle or bottom of this list.

    Ground rules

    × Big name guys that are staying put are not ranked (Steph, KD, etc)

    × All the amounts are expressed as averages over the course of the deal

    × You can’t win picking all the low cost guys because your team will never get anywhere good, so you do have to take a shot on high-end guys when the going is good.

    × I’m going to use a term called expected value in a few spots and that should be taken as the consensus or market value for a player when they sign their deal. If they are a positive expected value that means somebody like myself thinks they’re going to outperform their deal.

    × These deals aren’t going to have this many options but it’s my way of indicating which direction the deal might go

    Find all of the other positions here

    Point Guard: Click Here
    Small Forward: Click Here
    Power Forward: Click Here
    Center: Click Here

    SHOOTING GUARDS

    The top of this list is going to create a stir but there is good value at the top before things start to really tail off at No. 6 and 7.  Luckily for decision-makers, the risks taken here won’t be franchise-altering kicks to the groin if they don’t pan out.

    Not listed: None.

    1. Dion Waiters

    Projected: $17 million per year for four years with a team option

    Waiters gambled on himself after the NBA marketplace collapsed on him last summer, which in of itself was one of the more amazing NBA stories of the year. The market was probably ready to pay him upwards of $10 million before pay slots got filled up and buyers got cold feet. He settled for $3 million per year for two years and a player option, which he is not taking.

    That’s the thing with Waiters. It doesn’t take much for him to shake your confidence. Early career woes, his hardened background and a playing style that only recently shifted toward palatable are all in play here. But let’s be clear — he has taken big steps after two solid deployments in Oklahoma City and Miami, where both franchises value culture and in the case of Miami, they are the only franchise that gets mentioned in the same breath as San Antonio these days.

    So this ranking should be controversial and deciphering this type of uncertainty is why GMs make the big bucks. It’s also the case that the shooting guard position isn’t exactly teeming with high-end talent, making this rank less nuts once you sort everything out.

    Kentavious Caldwell-Pope is going to get around $25 million and just got suspended for two games due to DUI. You’ll see that Tim Hardaway Jr. is right on Waiters’ tail in these ranks but does he have his grit on either end? Have we even seen peak Waiters yet?

    I love THJ’s game and I am generally a fan of KCP, and certainly there are some legitimate reasons that NBA squads scattered away from Waiters en masse last year, but that’s the appeal here.

    Waiters is going to come at a discount and all of the indicators working against him don’t reflect the reality from the last 18 months. It’s a classic case of perception bias and purchasers could be getting something of a championship-level No. 4 or 5 starter. But he can easily be a quality No. 2 or 3 player for a rebuilding or middle-of-the-road squad, too.

    In a shooting guard market that is paper-thin this makes Waiters a fit for a lot of squads at a position of scarcity. Will he get his first big payday and somehow slip? It’s possible. But finding players that truly have confidence, that can gear it up and play both ends of the floor are hard to find.  This one just happens to have his own island named after him and that in part is why he has this type of value.

    VERDICT: Four years and $52 million ($13 AAV).  Waiters, like James Johnson, respected what the Heat have meant for his career and the Heat respected what Waiters gave.  Neither player shopped the market at an obscene level and even with the Gordon Hayward chase, they clearly didn’t feel pressure to go out and find other deals. 

    Both took undermarket deals and this is another steal for the Heat, which was aided in part by the chilled free agent marketplace.  Even though he’s somewhat duplicative of other pieces they have, it’s a best-case scenario for his career that he stays in Miami. 

    GRADE: A

    2. Tim Hardaway Jr. (RFA)

    Projection: $19 million per year for four years

    THJ’s season was fairly under-appreciated after he showed that he can be a high-end scorer throughout the next segment of his career. Defensively, he’s not winning any awards but he has the athleticism to not be a lost cause. Playing under Mike Budenholzer and being brought along mindfully by the Hawks, Hardaway Jr. has shown all the classic signs of a late bloomer.

    I do think it will be interesting to see if there is any pushback internally on this kind of an offer after Kent Bazemore’s first season was a relative bust. I highly doubt that, however, given the amount the Hawks have invested into him, and the next question is which team will step in and try to make the Hawks think here.

    I’d have him at No. 1 if I didn’t have to gamble four years at big money, because there is some chance Hardaway peaks out at a lower level than we hope, doesn’t develop on defense and becomes a long-term drag to your team’s cap.

    3. Kentavious Caldwell-Pope (RFA)

    Projection: $25 million per year over four or five years (team option for five years)

    Caldwell-Pope had a somewhat lost season with his sub-40 percent shooting, his general disappearance from the offense at times, and his disappearing act in losses as he shot just 34.7 percent from the field in 43 such games.

    If we look back to the start of the season before last, KCP had shown signs that he could be a very solid two-way player with upside.  Unfortunately, various injury issues this year and last (shoulder, knee, groin) have played a role in stalling his progress.

    Coloring his evaluation is the fact that he did play on a team that doesn’t scream leadership. Reggie Jackson was/is a mess, Andre Drummond has been miscast as a franchise player, Tobias Harris can’t get his if Reggie keeps chucking it up, and Stan Van Gundy hasn’t been the button pusher that many around the league hoped he would be.

    It feels like the league-wide perception of Caldwell-Pope is that he is a player that you do want to tie up to a long-term deal — and that he can approach max money for his bracket.

    If this position had any depth at all, he’d dip further down the list because at this rate he has two issues.

    One, he has very little chance of outperforming his deal even if he continues to improve. Two, he might not improve much if at all and then he’d be a decent-sized mess for the team that signs him.

    4. J.J. Redick

    Projection: $19 million per year for four years with a player option

    Everybody will moan and groan about this because of his age and even some recent injury history, but the one thing a team purchasing Redick knows is what they’re getting.

    At age 36 in the fourth year of this deal he’ll still be able to run around screens and drill 3-pointers, which will have value even if he’s upside down at that point and eking everything he can out of positional defense.

    Teams like the Nets and Sixers have already expressed interest in him as the second and third (or fourth) tier teams look at him as an attainable free agent. Sure, contenders would love to try and sneak him in for about half that number, but Redick would be nuts to leave that kind of money on the table unless he thought he was stepping into a sure thing (which doesn’t exist).

    Make this number $15 million and based on pure consistency he’d jump right to the top of this list.

    VERDICT: One year and $23 million to play for the Sixers.  Redick didn’t like the market and having lacked a real payday in the past he opted to make a one-year bet on himself, which is a bit dicey at his age but the reward was nice enough to avoid a bad long-term deal.  His shooting and savvy will be a necessary component of the Sixers’ squad next year and they’ll get ample value while not tying up long-term cap space. 

    GRADE: B

    5. Jonathon Simmons (RFA)

    Projection: $17 million per year for four years with a team option

    Simmons is going to be on everybody’s radar as we enter free agency and there is a very real question whether the Spurs are going to want to pay him top dollar. And they’ll have all the corporate intel about whether that is smart or not.

    The pros are pretty easy here. Simmons has shown elite athleticism and an improving all-around game that projects well if he can keep it up. He’s also 27 years old and the late-bloomer thing might have already run its course. Or it’s close.

    I also noticed a lack of explosion in the playoffs this year and that would concern me on a few levels, but mostly because players that haven’t earned their first big deal will play through anything to get to that deal, especially in the playoffs.

    So this is your classic athletic/upside contract play that decision-makers are tasked with every year. Simmons gets good marks for the intangibles and he’ll have the Spurs pedigree to take with him. The question will be if he profiles as well as a No. 3 guy with everything that comes with it on the scouting reports and with the improved competition he’ll face.

    Looking at the ranks these top five picks are somewhat interchangeable, with the group of Kentavious-Caldwell Pope, J.J. Redick and Simmons being easily re-ranked by fit.

    6. Manu Ginobili

    Projection: $10 million per year for two years (player option, partial guarantee on Year 2)

    Ginobili is 39 years old and the second year might just be so he signs a deal for the first year. He’s a coach on the floor and he showed in these playoffs that he can still play.

    The plan is simple in San Antonio and he’s barely worth ranking because we know how this story ends, assuming he returns. He’ll be on a pitch count all year and we’ll see a 40-year old man dunking on somebody in next season’s playoffs.

    7. Ben McLemore

    Projection: $9 million per year for three years (team option)

    McLemore was raw when he came into the league and subject to the Pete D’Alessandro era of Kings basketball. During that time he had to deal with the organizational chaos of his tenure which was all magnified by the friction that followed DeMarcus Cousins around.

    There will be more than one basketball decision-maker that thinks they can do better than that. So what will they have in Ben? He has a strong shooting stroke and he can jump out of the gym. He has the athleticism to become a good on-ball defender. Everything else is a mess including ballhandling, basketball IQ, off-ball anything and he has no problem jumping into his own head.

    A good organization with solid veteran leadership would be the ultimate contrast for him and at this type of money and risk – this is a sneaky, savvy play that might even be had for less.

    VERDICT: McLemore agreed to a two-year, $10.7 million deal and it was yet another example of the depressed marketplace.  The Grizzlies really did a good job with limited cap space to get an upside play that has court experience at a bottom barrel cost. 

    GRADE: B+

    8. Justin Holiday

    Projection: $11 million per year for three years (team option)

    Holiday never really got his game going in New York and this will be another evaluation where decision-makers believe they can do better than the dysfunctional Knicks. Holiday can do a little bit of everything and has a lanky, athletic quality that always has a place in the NBA, so long as the skills and execution keep up.

    He needs to find a solid organization that can put him in a position to showcase his talents as well as help take his game to the next level. A contender that can shoehorn him in would be making a strong move because he can make them younger and also contribute right away.

    9. Nick Young

    Projection: $11 million per year for three years (team option)

    The Swaggy P reputation of being a handful has eclipsed the reality of the 32 year old’s approach to the game nowadays. Yes, he’s going to shoot his shot and maybe another one, but he’s at a point in his career where he’s a known quantity. He can step in and fill 20 mpg without a problem, maybe more, and give you consistent results over the course of a season.

    He profiles best on a contender that is trying to simply avoid hitting rock bottom on the wing. Young isn’t going to be a bad guy off the floor, but putting him around young players hasn’t been great in L.A. and teams can probably do better. All said, this is a low cost to find a player that can step in and take shots.

    10. Tony Allen and Kyle Korver

    Projections: $10 million per year for two years (player option) and $8 million per year for two years (team option), respectively

    To be clear, either player could opt to take the veteran minimum if they want to chase a ring. But gauging what it would be worth to win either guy’s services, these are probably the amounts.

    There are people around the league that think Allen is still an elite defensive player, as he just got an All-Defensive Second Team nod this past year. He has been passed up by guys like Garrett Temple and is declining in that area, but somebody will be willing to pay for a poor man’s version of what he brought.

    As for Korver, he hasn’t looked great but Cleveland is a unique situation and you never know what an offseason of rest can bring. He’s a shooter with size and good fundamentals — that will keep him in a rotation for at least next season.

    Both are your typical veteran at the end of their career plays that can spin any direction, but unless you’re getting them at a discount they’re not going to sniff positive expected value.

    KORVER VERDICT: Korver got three years and $21 million and he’s a rare example of outperforming the market slowdown, which pretty much sums up the Dan Gilbert experience.  There’s a very good chance he’s not a good backup, which renders this contract mostly useless. 

    KORVER GRADE: D

    THE REST

    12-Who Cares: James Young, Ian Clark, Gerald Green, Jodie Meeks, Alan Anderson, Vince Carter, Randy Foye, Jason Terry, Anthony Morrow, Brandon Rush, Sasha Vujacic

    James Young is interesting just to see if you get lightning in a bottle (within reasonable expectations of course). Ian Clark is an ideal target for your bench but he might get a double-digit cash number because of his time with the Warriors and some of the flashes he showed there. This makes him a less attractive asset but I’d lean toward adding him over the Allens and Korvers of the world.

    The rest of this list is fatally flawed in one way or another.

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