It could have been slightly better, it could have been slightly worse.  Either way, the 09/10 NBA luxury tax will be set at $69.92 million, a little over a million less than it was a year ago.  Assuming the Bucks cut Bruce Bowen before his contract becomes guaranteed on August 1, the Bucks would have a $63.56 million cap number for 14 players, including Brandon Jennings and Jodie Meeks but excluding Ramon Sessions or Ersan Ilyasova.  That would look like this:

That gives the Bucks $6.36 million left under the tax to work with, likely not enough to re-sign both Sessions and Ilyasova.  Then again,  in order to sign both they'd also have to get rid of somebody else along with Bowen to stay at the max roster size of 15--most likely by buying out Kurt Thomas, cutting Salim Stoudamire or doing a package trade that sends out more guys than it brings back. 

That leaves the Bucks in an interesting/difficult spot.  Ilyasova needs to opt out of his Barcelona deal by July 15 to play in the NBA and the Spanish media was already predicting his return to Milwaukee last weekend, so he's probably the first player whose fate will be determined.  If the Bucks want to guarantee they have the cash to keep Sessions, the simplest plan of action would be to let Ilyasova stay in Barcelona another year.  Passing on Ilyasova would leave them with Amir Johnson, Thomas, and doses of Luc Mbah a Moute, Joe Alexander, and Malik Allen at the PF spot, though Luke Ridnour would presumably be traded at some point for help at the forward position as well.  And I haven't even mentioned Josh Childress, who would be a very nice addition--but mainly if it's as part of a sign-and-trade.  Like Ilyasova, Childress needs to opt out of his European deal before July 15, so we shouldn't have to wait long to know where he's going to be next year.

But what if the Bucks sign Ilyasova for a deal starting at, say, $2 million?  Based on recent suggestions in the JS, that seems like the most likely outcome.  That would leave just $4.36 million to sign Sessions, which superficially would appear to be a problem. With the MLE at $5.85 million, a team like the Knicks or Blazers could sign Sessions to an MLE-level deal and force the Bucks to go over the tax to match.  However, we know the Bucks would have to get rid of someone aside from just Bowen in that scenario, which would free additional dollars.  As a 14-year vet, Thomas would get a minimum of $1.3 million if he was signed by another team, which would put the Bucks on the hook for at most $2.5 million of his $3.8 million deal if they tried to buy him out.  Signing Ilyasova would also mean less need for Thomas in the frontcourt, though Thomas can also guard centers while Ilyasova is a combo forward.

The Bucks could also ship Thomas to a team with cap space or a trade exception (probably for the right to exchange second rounders or something else very token) in order to clear his full salary, though few teams would have that ability and none probably would be interested at that price. Cutting Stoudamire could also save a few hundred grand given that his $884k salary is only partially guaranteed.  Bottom line: if the Bucks really want to keep Sessions, they should be able to do it.  The tax isn't assessed until the end of the season and the Bucks have $22 million in expiring deals, so there would be plenty of opportunity to trim the payroll by a million or two between now and mid-April. 

Still, the fact that the Bucks haven't been vocal about matching offers for Sessions suggests they will be somewhat cost-conscious and will likely prefer not to do a four- or five-year deal.  But as much talk as there is about Sessions getting interest from a dozen teams, the number of teams willing to risk extending an offer sheet for a week will be much lower.  The Knicks are one obvious threat, but signing Grant Hill to a multi-year deal may mitigate that. And while I wouldn't expect it to happen, the Blazers could offer a deal that escalates above the MLE beyond the third year (as mentioned at Blazer's Edge).  I can't see the Bucks matching that kind of contract after they've just drafted Jennings.

While I wouldn't have a problem buying out Thomas to re-sign Sessions, Thomas would be a nice asset to keep--not only is he expring, but he can rebound and defend both big positions, something the Bucks have lacked in recent years.  However, Amir Johnson will also help in those departments and Ilyasova looks like he's ready to contribute after his Spanish detour.  There's also something to be said for rolling the dice on a cheaper, younger option like Ilyasova.  He doesn't have the dynamic offensive game to be a star, but his outside shooting and scrappiness defensively and on the boards could make him a key contributor.  So while Thomas makes a lot of sense for a contending team, Ilyasova would seem a better match for where the Bucks are--a young, fringe playoff team that needs to acquire more young assets before it can truly contend.  No matter what happens, the Bucks won't be entering the season with much star power at the forward positions, but they should at least have better athleticism and defense than a year ago.

What about 2010?

Interestingly, the NBA also issued an advisory that the tax and cap will likely fall further next summer when the full effects of the economic downturn are felt.  Since the tax is backward-looking, that's not too suprising--afterall, last season's marketing deals and season ticket subscriptions were mostly locked in when the economy went in the tank.  Dan has a very good summation of that issue over at RealGM. 

Fortunately, having all those expiring deals should afford the Bucks some freedom next summer.  Not that they'll have cap space to go after any big-ticket free agents (who, let's be honest, wouldn't sign here anyway), but at the very least they should be well under the tax and won't have any major pieces heading to free agency--unless Amir Johnson has a breakout season, which would be a nice problem to have. In that case, the Bucks would also retain Johnson's Bird rights, allowing them to offer him more money than any other team.