Should The Bucks Extend Brandon Jennings's Contract This Year?

It doesn't take much to stir up a firestorm of drama when it comes to Brandon Jennings and literally anything he says. "Keeping my options open" quickly becomes, "AAAGH I HATE THIS PLACE WHEN CAN I LEAVE???". Any expression of desire for a long-term deal might as well be a rehashing of Stephen Jackson's introductory press conference with the Bucks.

It's a blatant example of the rampant exaggeration that follows basically every statement by high-profile professional athletes. For individuals who have entirely predictable motives, and tend to communicate those motives with the same old cliches year after year, we put an awful lot of stock in in the words they choose to use.

This isn't to say the issue of a Brandon Jennings contract extension is a small one, though. Quite the opposite: it's one of the biggest questions facing the organization. Jennings has intimated he'd like to be the face of the franchise (again, who wouldn't want to hold such a title?), but is he worth matching dedication from the franchise itself? The clock might be ticking already.

The deadline for Jennings to sign an extension this year is October 31st. If Milwaukee doesn't ink him to a long-term deal before then, they'll have to wait until next summer. There's little reason to think the Bucks don't want to retain Jennings' services, it's simply a question of how much those services will cost. Could Jennings be lured by a big offer from a more glamorous town? The Bucks have most of the power if they're determined to continue building around Jennings, but timing the requisite extension right could pay major dividends. So should Milwaukee make a hard play at getting Jennings' name down on the dotted line, or would they be better off waiting until next year?

The Case For Extending Jennings This Year

Like basically every other Brandon Jennings-related topic, it's mostly about potential. In general terms, Brandon has improved in each year of his career. Much of that improvement is owed to an ever-decreasing turnover rate, already at an elite level. A jump in shot attempts at the rim (and an even bigger jump in shooting percentage there) also helps. But other parts of his game have stagnated or declined. His three-point shooting remains uneven at best, and his assist rate hasn't rebounded to even the modest levels of his rookie season. And so we're left estimating where Jennings' true talent level rests, with evidence to both hypotheses. Signing him to an extension now is banking on that improvement, assuming you'll get positive net-value by getting in while the getting's good. The good news is that lots of the stuff Jennings struggles with (shot selection/efficiency) are the sort of things players continually improve in, while some things he's already great at are trickier to teach.

It's not just Jennings himself the Bucks have to contend with at the negotiating table, though. Outside demand for a player is a critical element in his valuation, so locking in a long-term deal before Jennings hits the open market could yield the biggest savings of all. The going rate for many of Jennings' contemporaries hasn't been set, leaving primarily lower-value contracts (which are looking more and more team-friendly) as models for comparison. Jennings' agent isn't going to lie down for just a few examples, but it certainly takes away some of his ammunition. Jrue Holiday's angling for a max extension, while ridiculous, won't help keep costs down. And a player with a legitimately strong resume, like Denver's Ty Lawson, can bump up the salary floor by virtue of simply playing the same position. He's a young point guard, Jennings is a young point guard, therefore Jennings deserves a comparable deal. Might it be worth avoiding that mess by putting together an extension early? It's undoubtedly a perk.

In addition, Jennings' relative durability saves some hesitation like that plaguing the Golden State Warriors, who would surely be dumping money in Stephen Curry's lap were they not concerned for the added weight it would put on his ankle. Brandon's only missed time in his career came after breaking his foot, an injury he unknowingly played through for about a game and a half. The foot bone may be connected to the ankle bone, but the danger of recurring injuries to non-joints is far lower.

Maybe it's fair to worry the whole contract situation could be a distraction as well, stunting Jennings' progress. Or maybe the impending negotiations will give him some sort of "contract year" motivation, artificially driving up his price. Neither occurrence is particularly easy to predict or evaluate, but a deal this year would preempt both.

The Case For Waiting Until Next Summer

With so much hanging in the balance for Milwaukee this season, one might argue holding off on the extension is the "safer" play. Scott Skiles and John Hammond are on the final years of their respective contracts, and the Bucks have less than $22 million in guaranteed salary on the books next season. Laughable as the concept of a full teardown might be to many of us, next season could be a very convenient time to start. If the Bucks aren't totally sold on Jennings as their veritable franchise player (a new coach and/or GM would make this question far more pertinent), allowing him to reach restricted free agency is less of an issue. History suggests rookies will take the biggest payday they can get on the first go-around, so if losing him altogether is Milwaukee's only real concern, it shouldn't be keeping them up at night.

It's also conceivable the same market people fear will drive up the price for Jennings could be thinner than expected. With a plethora of point guards looking for new deals (albeit mostly of the restricted variety), the supply of young, somewhat-unproven guards might exceed the demand. If Jennings turns in a performance comparable to 2011/2012, he might not command the sort of contract value he and his agent hope to get. Another year also brings us that much closer to the steep luxury tax penalties that go into effect over the next few years. The contracts handed out this summer don't inspire a lot of confidence in that regard, but when owners' wallets start to really feel the pinch, things could change pretty quickly. That would force/allow (however you want to look at it) Milwaukee to reassess Jennings' role with the franchise. Perhaps they retain him at a lower cost and move him to a 6th-man role, a spot many among us have speculated could be a better fit for his style and ability. Perhaps another team values Jennings more than Milwaukee, opening the possibility of a sign-and-trade. One would imagine such a move might be coupled with a more extensive rebuilding project. Either way, it's hard to imagine there being more questions about his future this time next year than there are right now.

There's also the ever-present market chatter that constantly swirls around Jennings. Another disappointing year in Milwaukee might turn him off the franchise entirely, if you believe he's already on the fence. Should that happen before an extension is reached, the Bucks could end up watching Jennings walk for nothing in a year, assuming he plays under the 1-year qualifying offer to reach unrestricted free agency in 2014. That feels a long way off, but smart franchises plan years in advance for a reason.

So What Should They Do?

If you ask me, the Bucks should be actively working with Jennings and agent Bill Duffy to get an extension done this summer. BUT, I use the word "actively" in contrast to "aggressively". If the team can parlay Jennings' apparent eagerness to get a long-term deal down on paper into reasonable savings, pulling the trigger is probably the right move. Frank has suggested--and it's tough to argue--Jennings' is unlikely to sign for anything less than $11-12 million. Should an agreement be reached in the $9-10 million range, it would seem foolish to pass it up. Barring such an unexpected opportunity, I don't see much point in jumping the gun. Bucks fans are more than familiar with Brandon's shortcomings, but we're still talking about the #16 per-game scorer from last season. There will always be teams willing to throw money at that kind of skin-deep production, regardless of how misleading it might be.

I'm of the opinion that signing players to team-friendly deals below expected value is, in general, a good move regardless of team situation. That sentiment feels obvious, though, which in turn feels like a subtle endorsement of the "safe" route. That's probably the more realistic path anyway. If the Bucks feel confident they can accurately gauge the market--and beat it--more power to them, but these days it seems there's no easy way to contend with agents and player markets and what-not.

So what do you think? Ink him now, or wait and see?