Milwaukee's salary-cap status is among the most fluid in the NBA because three prominent free agents -- Brandon Jennings, Monta Ellis and J.J. Redick -- could be re-signed to substantial deals or let go to create space. Until a decision is made on each of those three guards, their cap holds will limit other moves and complicate an already messy cap picture. If all three relocate and Milwaukee uses the amnesty provision to release Drew Gooden, the Bucks could have upwards of $30 million in cap room. If all three are re-signed, Milwaukee could be left to enter next season with essentially the same roster that was swept in the first round of the playoffs.
Within that variance lies a number of possible offseason trajectories for Milwaukee, each in some part reliant on the domino decisions of the team's free agents. This summer is a valuable opportunity for the stagnant Bucks to plot out an actual course rather than stockpile middling assets, though doing so will require difficult decisions from general manager John Hammond and the potential departure of seemingly valuable players. Such is the nature of a league where retaining moderate talent isn't always worth the corresponding opportunity costs, particularly in the case of a team that very much needs to reshuffle its assets.
The best-case scenario: Milwaukee re-signs Jennings and Redick to reasonable, movable deals while letting Ellis walk.
The backcourt pairing of Jennings and Redick is hardly perfect, but if both can be signed to affordable contracts, the Bucks would do well to make that commitment. Milwaukee's salary structure would allow for the re-signing of both players while still giving Hammond a nice slice of cap room with which to land a notable free agent or two. With the right additions, Milwaukee could tab Larry Sanders, John Henson and perhaps Jennings as long-term pieces, while shopping Redick eventually and using his helpful game in the interim.
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The crux of these decisions isn't merely the choice of which players to keep, but at what price. Jennings and Redick will both be in relative demand, but Milwaukee shouldn't overpay for the sole purpose of retaining those nonessential pieces. If Redick draws an attractive offer elsewhere, the Bucks shouldn't over-inflate theirs in an effort to justify his midseason acquisition. If a desperate suitor signs Jennings to a massive offer sheet as a restricted free agent, Milwaukee would be wise to see him out the door.
What the Bucks must avoid is committing to Ellis in a way that they already seem willing to do, based on a two-year extension they reportedly offered that -- when combined with his $11 million player option for next season that he has now rejected in order to become a free agent -- would have resulted in a total package of three years and $36 million. Ellis, 27, may be an effective shot creator, but his re-signing would bring numerous concerns because he requires a highly specific supporting cast to compensate for his shortcomings. His presence would necessitate other perimeter players capable of cross-matching on defense to hide Ellis from tough assignments. He would need perimeter teammates with long-range games because of his weakness as a three-point shooter. And perhaps most problematic of all: He badly needs a teammate who can strike a perfect balance of sharing the responsibilities of shot creation, as Ellis' game devalues when he dominates the ball or attempts to work purely off of it.
These aren't impossible considerations to account for, but it dramatically increases the inherent challenge of building a contender from the ground up with Ellis as a centerpiece. Milwaukee has no clear-cut star player or a wealth of talent in general. But that doesn't make Ellis -- who can create like a star guard, on occasion -- a worthy investment at so high a cost.
The worst-case scenario: Milwaukee signs Ellis to an above-market contract (such as that three-year, $36 million package), matches a huge offer sheet on Jennings and lets Redick walk.
Bringing back Ellis and Jennings, a misfit backcourt on both ends of the floor, would damage a Bucks team that needs to shake up the status quo. Hiring Larry Drew as coach provided a nice start, but Milwaukee can only make further gains through additional changes. That begins with parting ways with Ellis, assuming his return demands the kind of salary that would tie up the Bucks' finances over the next few seasons.
In Jennings' case, Milwaukee needs to structure any potential contract with the aim that it be tradable. Every dollar saved doesn't just benefit the team's bottom line but also helps its greater flexibility. The Bucks are likely best served keeping the 23-year-old guard for now to see how he might fit with a renovated roster, but his re-signing would also be about the potential to redeem Jennings' value via trade. It's crucial that both options be viable, lest Milwaukee stick itself with an unfortunate contract and a difficult player for several seasons.
As for Redick, his departure would mean the loss of both a starting-caliber guard and any long-term return for his acquisition. Milwaukee's deadline trade for the soon-to-be 29-year-old was largely a move to acquire his Bird rights and gain the upper hand in competing for his services on the market this summer. By virtue of having those rights, the Bucks can go over the cap to re-sign Redick (crucial given the cap holds on Ellis, Jennings and Milwaukee's other free agents, including Mike Dunleavy) and offer him a five-year deal with 7.5 percent annual raises while rival suitors would be limited to four-year deals with 4.5 percent raises. That won't much matter if Redick decides to sign elsewhere, as is rumored, and if that's the case, Milwaukee will have traded one rotation player on an expiring deal (Beno Udrih), one solid prospect (Tobias Harris) and another decent project (Doron Lamb) to Orlando for 32 games of Redick.
The likely outcome: Milwaukee re-signs Ellis, brings back Jennings for one more season on a qualifying offer (after failing to agree on a possible extension) and loses Redick in free agency.
Based on the Bucks' reported interest in re-signing Ellis to a baffling sum, they would seem to be the early front-runners for him. He's sure to test the market, as Ellis will be giving up an $11 million salary for the freedom to pick his team and the opportunity to secure a longer, more lucrative deal. The Bucks may not offer a change of scenery, but because of the holes in his game, Ellis could be hard-pressed to beat Milwaukee's reported $36 million offer.
That could put Milwaukee in an odd place in its negotiations with Jennings, especially given that the two parties were rumored to be so far apart in their preseason talks on a possible extension. Not much has changed regarding the franchise's position or Jennings' performance to expect a compromise, which would put the ball in the hands of Jennings and any team interested in signing him to an offer sheet. The Bucks would have the right to match any rival's offer, part of the reason why I see Jennings playing out one more season for the Bucks on the qualifying offer in order to become an unrestricted free agent next summer.
Even if Jennings were able to find a good match, he'd only have the ability to leave as long as the Bucks would allow it -- as opposed to the more literal free agency he would enjoy next time around. Jennings stands to be a bigger fish in this summer's relatively meager free-agent pool, but next year could yield a greater number of teams with cap space intent on using it, not to mention Jennings' benefit of selecting a new team without fear of the Bucks matching his offer. If Jennings really is intent on leaving Milwaukee, as has been rumored for several seasons, the wait for unrestricted free agency is the means to accomplish that goal.
That said, there's still a decent chance that Jennings finds and signs an offer sheet, leaving his situation the most unpredictable of the three guards. Redick seems as good as gone, as his slumping performance in Milwaukee and likely interest from contending teams would give him all the more reason to leave. Redick has no loyalties to consider in weighing a return to a team he joined in February and little basketball motivation in signing with Milwaukee over a more viable team. He'd fit nicely as a mid-level addition on a lot of teams, the majority of which would likely be more palatable alternatives to serving as a likely backup to Ellis and Jennings.