History gave the Spurs a quota of luck you can't assume will repeat itself.
Had the Spurs not landed Duncan (~80% chance it didn't happen) David Robinson would have surely retired ringless, they didn't "naturally" develop anything, Tim just fell into their lap by chance and landed on a very different situation to the one Wemby will find himself in right now.
Had Tony and Manu not reached their absolute best case scenario, Tim probably doesn't get that second ring and could very well have gone elsewhere in free agency (he almost did in '00). Don't get me wrong, the Spurs' scouting was great and deserves a lot of credit especially with Tony, but if you think they knew what Manu would become you're deluding yourself. You can't rely on finding that kind of talent at the right time every time with crappy picks, that's an anomaly that has given some a false sense of security.
My point is, putting together a championship contender isn't easy, and you can't take for granted it's naturally going to happen. Also take into consideration the clock is ticking, because if you haven't found those pieces midway Wemby's rookie extension, chances are he'll push for a trade to another team.
The Spurs have as much freedom to take chances as they're going to have in the foreseeable future, not taking a few more chances at top young talent now would be a costly mistake down the road, I hope the FO doesn't make that mistake.

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