Ever since the New England Patriots began winning regular season football games at will, the popular question that I’ve asked myself time and time again is “what constitutes a successful season?” Since I started, I can’t stop. Being a Boston sports fan, the answer to many of these questions is almost always something different from fans of other teams in the same league. Yet, I’m also a Notre Dame basketball fan, which means that my idea of a successful season – which this year, to me, is an NCAA tournament birth – is far different than my answer to the same question when discussing UConn men’s basketball and I don my blue and white (don’t ask how I get two teams in the same conference, I don’t know the answer).

How does this lead me to this season’s Boston Celtics team? For the last four seasons, beginning in 2008, the answer to that question has been “win an NBA championship”. This year is different. With established powers of Dallas, Los Angeles Lakers, and Miami; emerging threats ready to take the throne such as Oklahoma City and Chicago; and flavor-of-the-month clubs like the Knicks and Clippers, it’s wholly unrealistic for me as a serious fan of both the Boston Celtics and NBA hoops to say that a successful year for this season’s club would be a trophy. And you can count me out from those group of fans whom, after cheering for a championship-caliber NBA team over the course of a few years, would be okay with a playoff appearance with a possible first-round win.

Here are the facts; as constructed, the Boston Celtics will not win the NBA title. They are a playoff team. They are old, and not getting younger. Their bench is a disgrace. The team signed an overrated head coach to a contract extension meaning he can coach them until he either (a) gets bored, (b) gets tired, (c) gets a better offer, or (d) a team drafts his son Austin Rivers and he gets the chance to go coach him. The Celtics have one remaining blue-chip player who may not be top-4 at his position (Rajon Rondo is not better than Chris Paul, Derrick Rose, and Russell Westbrook – take your swings at Deron Williams and Steve Nash).

That’s why a successful season will end with a roster of nobodys, Rajon Rondo, Brandon Bass, and a plethora of draft picks. Preferably, the team with some of the most expensive tickets in the league will finish behind the aforementioned Heat, Bulls, and Kicks, along with the Pacers, Magic, and Hawks. Yes, they’ll be a playoff team in that case, but a mid-range pick in a deep draft is solid. Plus possible picks from trades of Ray Allen, Kevin Garnett, and Paul Pierce would land multiple selections in the 2012 Draft, along with others in upcoming years.

I’ve been wrong about this before. I suffered through the horrendous 2007 Celtics season and prayed for losses every game, ensuring the first pick in that year’s NBA Draft which would give us Kevin Durant (it was clear that general manager Danny Ainge preferred the Texas prospect over Ohio State’s Greg Oden).

This is different. Whether or not Celtics management likes it or not, the Boston fans have become accustomed, again to winning. So I understand why they might be hesitant to pull the trigger on such moves – especially the Pierce trade. Pierce is an icon in the city of Boston – up there side-by-side with Tom Brady and David Ortiz. Rightfully so. And when the day comes, the number 34 will hang from the rafters of the Boston Garden and Pierce will enter the Hall of Fame sporting Celtic green. But more so than winning, what is most important this year is progress. Progress in the plan of this franchise. Does Ainge go out and pull off a trade for Dwight Howard? Maybe. And while I would have supported a Rajon Rondo-for-Chris Paul trade at the beginning of the season, it would have extended the Celtics window for a title by this season only. Only two players on the current roster should be in Celtics uniforms on opening night next season – Rondo and Bass. Rondo is the future, a player who with continued work can eventually become one of the greats. The vision, passing, quickness, and defense is all there. The shooting and leadership is not. Shooting can be improved with work, and leadership will come once the “Big 3” are gone. As for Bass, there is perhaps no other player I’ve been as impressed with in the team’s first six games this season as him. I think that his future is sky-high, with a caveat being that he must learn that at times, a pass is as good as a shot. Perhaps Avery Bradley should also stick around, and with continued playing time that will become clearer. A great defender and only in his second year, he needs to game experience before anybody casts a vote on his future in the league.

It’s time for Ainge to befriend the likes of the Heat, Bulls, and Clippers. I certainly would have said Knicks or Pacers rather than Clippers, but Pierce would need to be traded outside the Eastern Conference, both for competitive purposes (Pierce likely will play longer than Garnett and Allen) and psychological purposes (Celtic fans never would want to face Pierce, say, 20 times over the next four years). But this makes sense, and this is business. And those who are casual fans – those who think Paul Pierce is a top-5 NBA player because he’s the best scorer on the Celtics and has won a title, or those who would have been crushed if the team acquired perhaps the best point guard in the NBA (Paul) for Rondo – will be up in arms. But others will understand. I will applaud. The biggest part of a general manager’s job is knowing when to move on. Ainge played for a Celtics team whose architect, the great Red Auerbach, did not know when to call it a day and turnover the roster. Today, Ainge can’t make that mistake because the franchise can’t afford it in today’s NBA climate.

The ball’s in Ainge’s court. He can make his run at Dwight Howard, which he will. But after coming away empty, he must make the most of this aging roster. Dare I say – his legacy may depend on it.