One issue will be decided in July when Greg Monroe makes his decision about where he is going to play for the next several years.
Monroe took a huge risk last summer, turning down Detroit's contract offer as a restricted free agent to sign a qualifying offer that was well below market value.
The move was a success when Monroe averaged 15.9 points and 10.2 rebounds and returned from a late-season knee strain to show that there weren't any ill effects.
Now, after not being able to sign him a year ago when they were the only bidders, Van Gundy and general manager Jeff Bower will be have to win an auction against the rest of the NBA.
"I don't know where that is going," Van Gundy said. "I told Greg today that he's done a great job of staying focused all season, but now he's got a couple months to think about his future and make a decision about what he wants for the rest of his career."
Bower hopes that after spending a season with Van Gundy, Monroe will want to stay with the Pistons.
"Greg has a lot more information than he did last July," Bower said. "He understands the culture and the chemistry of this franchise, and he understands how Stan plans to move it forward. He has to take that information, compare it to what he wants and make his decision."
The Pistons have contingency plans in place for players they would pursue in place of Monroe, but the second issue is trickier. Brandon Jennings was playing at an All-Star level when he tore his Achilles' tendon in January and the Pistons won't know much about his recovery until this fall.
"That's the real X-factor this summer, because we have no idea what is going to happen with Brandon," Van Gundy said. "We won't know in July, and we won't know until he gets on the floor and plays in some regular-season games so we can gauge his recovery level.
"That's a tough injury, but he's young and doesn't carry a lot of weight, so we're hopeful, but we really don't know."
Detroit has already acquired a long-term replacement for Jennings in Reggie Jackson. He had a tricky adjustment period with the team — they went on a 10-game losing streak after acquiring him at the deadline — but put up a pair of triple-doubles and a 20-point, 20-assist game down the stretch.
Van Gundy makes no secret that he plans to build the roster around Jackson and Andre Drummond, who averaged 13.8 points and 13.5 rebounds.
"Andre is still only 21 years old, and he's doing things that are unprecedented for someone that age," Van Gundy said. "He's not a finished product by any means, but we saw a bigger step from him offensively than we expected to see in our first year."
The Pistons only improved by three wins over the previous season's 29-53 mark, but Van Gundy is much more optimistic about the state of the franchise than he was a year ago.
"I'm never going to be giddy about a 32-50 season, but I definitely think we are in a much better position now than we were a year ago," he said. "We've got Andre and Reggie, we've got KCP (Kentavious Caldwell-Pope) who took a leap forward this year and who has the potential to take another one, and we've got great chemistry and culture.
"Now we have to add talent, both through free agency and the draft, without hurting the culture that we've built here."
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