"When you use terminology like, 'We're trying to figure it out,' people probably think you've got to be better and you've got to be smarter than to use terminology like that," Hammond said. "But that's where we are. We're a work in progress, and I don't know what road we're going to go down. Can we eventually acquire enough young assets? We have some now, and we're going to have to acquire more. Can we acquire a group that's good enough to contend?"
The Bucks aren't seeking to trade Jennings because they want to keep him and because they're trying to make the playoffs -- trying to win even as they rebuild with youth.
"Everybody wants young players, and they want to see a bright future, but obviously they want to win," Hammond said. "I always talk about what Danny did." He was referring to the course established originally by Celtics president Danny Ainge, which was to rebuild through the draft. Then the Celtics lost the 2007 lottery, and Ainge traded most of his young assets for veterans Ray Allen and Kevin Garnett.
"He sits here today with a championship and still a very competitive team," Hammond said. "And that's where we want to be someday."
That's the ultimate example of figuring it out along the way. The best plans are subservient to unpredictable events.
The Thunder serve as a model for how to develop a small-market franchise. But the Thunder established their foundation of young players first by picking No. 2 when a franchise player was available, which was fortunate because a star like Kevin Durant isn't on the board every year; and also by losing an average of 55 games for four straight years, which is something the Bucks haven't been willing to endure.
"Oklahoma City was built with the second pick, the third pick, the fourth pick and the fifth pick," Hammond said. "The projection for our team going into the season is, if they don't have us as a playoff team, they have us right at the cusp of being in the playoffs. So we're still trying to serve two masters, to be honest with you. We're trying to win now, we're trying to do it with young talent, we're trying to do it with a fair salary structure.
"A top-five pick has a 42 percent chance of being an All-Star," added Hammond, referring to a 20-year study of NBA drafts. "In the last few years, we haven't been drafting in the top five. We've been in the 10-through-15 range the last four years, and it's difficult to do it that way.
"I hate to say these kinds of things because when you're an NBA general manager and you say we're still trying to figure it out, people say you've got to give me something better than that. But sometimes that is the terminology that is appropriate for what we're going through right now. ... I hate to go to the word luck, but small-market teams still need that luck. You need that lottery ball or that pick to fall your way."