If he's going to be around, John Hammond will likely have a busy summer yet again. (Getty Images)

Watching Stephen Jackson thrive off the bench for the San Antonio Spurs yesterday was neither super enjoyable for me nor surprising. I can only assume John Hammond felt the same way.

The Spurs brought Jackson in to be an extra lift. To give the bench some more life. He isn’t getting top billing, he’s just a supporting piece. In that role, Jackson apparently can still flourish.

In Milwaukee, Jackson was the focus. He had no established stars or leaders around him. He had a lot of responsibility both on the court and in the locker room. He couldn’t handle it on the court and as soon as things faltered out there, he became too much to handle behind the scenes apparently.

His problem in Milwaukee was that he was out of place. That appears to be the Bucks biggest problem across the entire roster. It’s not that the Milwaukee Bucks don’t have talent. They have a number of talented players. But most of the Bucks are one or two spots above where they should be.

Carlos Delfino is a fine player, but he isn’t really an ideal candidate for 30 minutes every night. Especially with the way he defended this season. He’s probably an eighth or ninth man who would thrive getting about 20 minutes each night.

Drew Gooden has talent, but aside from playing out of position at center, he’s out of his role as a cornerstone of an offense. In his two seasons in Milwaukee he’s been attempting more shots than ever before and responded with two of his worst shooting seasons as a pro.

Up and down the Bucks roster, players are forced to take on more than they can chew. Brandon Jennings isn’t really cut out right now to be the best player on a team. Monta Ellis has gone through his entire career as a 20 point and 20 shot per game starter when he’s pretty much Lou Williams and should be coming off the bench or a third option starter.

Hammond does have an eye for talent. He can recognize players that can play. Unfortunately, the pressure to make the playoffs has resulted in him and Scott Skiles reaching when it came to fit. The two of them have been forced to try and squeeze too much out of a number of guys. The biggest question facing the Bucks roster now, as it so often seems to be come summer time, is how can Milwaukee get players into roles where they can succeed?

With so precious few assets, it seems almost impossible. Milwaukee is a star away from being in pretty good shape. An actual star would allow everyone to slide back a bit into more natural and comfortable roles and responsibilities. But nothing in the NBA is as difficult as finding a star.

So the rumblings of John Hammond heading to Portland are hardly surprising. How much further can this roster go? How long can anyone keep making a series of overhaul tweaks every summer before just walking away? For every Mike Dunleavy who finds a spot that works for himself within the team’s structure, we seem to see a Corey Maggette who just doesn’t work.

So this week is a critical one for the Bucks.

We’ll likely learn a lot more about the futures of both Skiles and Hammond. Conversely, we’ll find out about the future direction of the franchise as well. While a blow up isn’t all that likely to come even if Hammond and/or Skiles leave, we can safely rule one out completely if they stay. Given how close they were to the playoffs, there’s enough reason for the current front office to spend another summer shuffling the deck and hoping the cards land more favorably.

Maybe they won’t be a factor in the lottery, but who’s to say the Bucks don’t need a bit of luck this summer. Here’s wishing it on them.

Jeremy Schmidt writes the Milwaukee Bucks blog Bucksketball.com. He’d love it if you stopped by every time you wanted to buy something on Amazon and gave him some click-through love on the banner up on the top right. Also –Twitter.