For the past three seasons, pundits have pegged the Trail Blazers as the NBA's up-and-coming franchise.

Before the 2008-09 season, everyone was calling the Blazers the best young team in the league. Before last season, Sports Illustrated picked the team to make the Western Conference Finals.

It's easy to see why: The front office assembled one of the league's best young rosters, centered on a Big Three (Brandon Roy, LaMarcus Aldridge and Greg Oden). The theory back in 2007, when the Blazers drafted Oden as the third piece, was that the trio would eventually grow into a powerhouse capable of matching up with the Los Angeles Lakers and Boston Celtics. In the regular season, the plan worked to the point that the Blazers have been very competitive: Portland won 54 games and a share of the Northwest Division title during the 2008-09 season, and somehow, despite a rash of crippling injuries, which caused Blazers to miss a total of 311 games last season (including 61 by Oden), the team still won 50 games.

That was then. This is now. As they open the season Tuesday, Oct. 26, against the Phoenix Suns (the same team that knocked them out of the first round of the playoffs last spring), the Blazers have reached a crossroads where those 50-plus wins aren't good enough. The team failed in attempts to land star point guard Chris Paul this offseason, and now return with almost the exact same roster that struggled in the playoffs. Yes, free agent guard Wesley Matthews is a nice addition, but barring an injury or trade he probably won't crack the starting lineup.

If the Blazers finally make it out of the first round, that's progress. But if they lose again, it might be time to start over. Here are the four people who have the most to win—or lose—this season:

Brandon Roy
Roy unquestionably is one of the league's best players when he's healthy—an All-Star shooting guard good for 20 points and five assists every night. But he also has a lot to prove at age 26 after four seasons. Is his right knee healthy after surgery to repair a torn meniscus? Is Roy the alpha dog who can carry the team out of the first round? Or is he better off as its second option? Roy recently said he wants the ball in his hands more this season. But if he can't coexist with point guard Andre Miller—a similar player who is also best when he controls the offense—new GM Rich Cho might do the unthinkable and dangle Roy in offers for a proven superstar.

Nate McMillan
When a team fails to live up to expectations worse than the series finale of Lost did, the coach is always the first person to get the blame. So while McMillan deserves props for guiding the Blazers from the bottom of the Western Conference to bona fide contenders over the past five years, it's on him to steer them this season into the second round. McMillan did an amazing job with an injury-riddled lineup last year, but his methodical, isolation-based offense doesn't always work in the playoffs, when teams force the ball out of Roy's hands. The coach's contract expires after the 2010-11 season, and McMillan could find himself on a different sideline if the Blazers fail to make a big leap.

Greg Oden
Is Oden a bust? With hindsight, it's impossible not to admit he was the wrong choice in the 2007 draft—No. 2 pick Kevin Durant is quickly becoming the best NBA player not named LeBron—but Oden can still be productive if he can just stay on the court. In 21 games last year, Oden averaged 11.1 points, 8.5 rebounds, and 2.3 blocks in just 23 minutes a game. But we're talking about a guy coming off a second knee surgery, someone who is known around the league more for his penis and brittle bones than his shot-blocking ability. At this point nobody knows when he'll return this season, but if he plays, he could be the difference between another early-round exit or a trip deep into the playoffs.

Nicolas Batum
Everyone in town is rightfully in love with the 21-year-old Frenchman. Batum is coming off a great summer spent with the French national team, where he gained confidence on offense that could lead to an expanded role with the Blazers. With Martell Webster traded away, Batum has the starting small forward spot to lose, and in the preseason McMillan even started calling plays for him. Is this the year Batum makes the jump from serviceable starter to budding all-star? Defense has always been Batum's forte, but an added offensive arsenal makes the Blazers that much more dangerous. If Batum doesn't improve, Matthews and his $33 million contract are there to snatch his playing time.