Mostly due to the city’s history of racial inequality, partially due to cold and snowy winters, the Boston Celtics have never signed a truly significant free agent. Bill Russell, Bob Cousy, Larry Bird, Paul Pierce, John Havlicek, Dave Cowens, Kevin McHale — name a Celtics superstar and he was acquired via trade or through the draft.

The most important free agent signing in franchise history was probably Don Nelson; before he became a zany, successful and entirely unpredictable coach, Nelson was a key figure, albeit a role player, on five Celtics championship teams. But even Nelson came to Boston with little fanfare and few other options — the year before joining the Celtics, Nellie averaged 2.4 points per game for the Los Angeles Lakers. And with the Celtics, he never averaged more than 15.4 points, 27.4 minutes, or 7.3 rebounds. The most important free agent acquisition in the history of the NBA’s winningest franchise never made a single All-Star game.

But Boston’s free agent luck might be changing. According to Stephen Jackson, players are beginning to look at Boston differently than ever before.

“When I first got in the league, I would never have thought about Boston. Ever,” Jackson told ESPN the Magazine’s Ric Bucher. “The way they embraced KG was a big part of changing that.”

The Celtics also have a coach, and a black one at that, known for treating his players well. The Boston players begged Doc Rivers to stay every time rumors flew saying he might take a leave of absence, according to Bucher.

“That’s a big piece of it,” one agent told Bucher. “They’d run through a wall for him.”

As the Celtics attempt to transition from the Big Three era to the “Rondo and whoever else” era, becoming major players in the free agent market has never been more important. The Celtics currently have only three players under contract for the 2012-12 season. That means Danny Ainge will have millions of dollars to play with in the summer of 2012, but convincing Dwight Howard or any other marquee free agent to sign in Boston will mean erasing five decades worth of free agent whiffs. And if Ainge does fail to upgrade the team through free agency, the Celtics could begin a long rebuilding process, one that could revive painful memories of Ricky Davis, Gerald Green and Sebastian Telfair. Either that, or Ainge could settle for second-tier free agents and the Celtics could become mired in what I will call “The Antoine Walker Zone,” where the Celtics make the playoffs every year but never have a chance to contend for a championship.

In his piece, Bucher discussed the possibility of a Jeff Green-Paul Pierce-Rajon Rondo core.

“A nucleus of Green, Rondo and Pierce ‘is definitely a playoff team, especially in the East,’ says an Eastern Conference executive who spoke on a condition of anonymity because the league has a $1 million gag order on its employees during the current lockout,” wrote Bucher.

But the playoffs are not supposed to be the end, not for the Boston Celtics, winners of 17 championships, but the means to the end. The Celtics are supposed to fight for championships, not resign themselves to mediocrity. The Antoine Walker era produced many memorable moments — banked three-pointers to win games, a trip to the Eastern Conference Finals, shimmies and shakes galore– but the era that came after it, the Gerald Green era, was more beneficial to winning a title than anything Walker ever accomplished in Boston. With Walker, the Celtics were stuck in quick sand, not going anywhere fast, pretending to make moves that would result in a championship but never really inching any closer. But after gutting the team and rebuilding with young talent (err, if you can call it talent), the Celtics were able to trade assets, contracts and draft picks to acquire the Big Three and bring Boston its 17th title.

In the summer of 2012, when Kevin Garnett and Ray Allen become free agents, Danny Ainge might have a choice to make: sign second-tier free agents and maintain a semblance of competitive mediocrity, or gut the entire roster and attempt to rebuild through draft picks and trades.

Or maybe, if the Celtics get lucky, if Stephen Jackson’s sentiments are shared by the rest of the NBA, or at least by the marquee free agents of 2012, the Celtics could skip the rebuilding process and simply reload.

What say you, Dwight?