Chris Paul isn’t just reportedly demanding a trade to New York (a report he and two league sources denied, for what it’s worth). He’s also reportedly reaching out to Dwight Howard in hopes that he and Howard can team together.

Would you like anything else, Chris? A rocket ship, perhaps? A date with Jessica Biel and Megan Fox, both at the same time? A parakeet that can fetch your coffee in the morning? (Yahoo! Sports)

Paul has reached out to Orlando Magic center Dwight Howard recently, encouraging Howard to find a way for the two to play together, sources told Yahoo! Sports. That would be a difficult scenario for the Knicks to make happen. Paul’s desire to join the Knicks was cemented after he spent so much time in New York over the summer with close friend Carmelo Anthony.

If Paul were to opt out of the final year of his contract and become a free agent after this season, he could sign a maximum four-year, $74 million deal with another team. The Knicks currently would have enough salary-cap room to offer him a four-year, $55.5 million contract with a starting salary of $13 million.

I’ve said it before and I’m saying it again. Ainge is planning his second coup of the past five years. He wants to reload on the fly, and he’s shooting to add both Chris Paul and Dwight Howard to the Boston lineup.

If Paul wants to play in New York and only New York, the Celtics are (obviously) screwed. But if he’s also open to teaming with Dwight Howard somewhere, there are two teams I immediately think of with the assets, management, financial flexibility and major market to entice the tandem: Boston and Los Angeles.

It’s still a pipe dream. A ridiculous, why-even-bother-thinking-about-it improbability. But Ainge has done it before.

The Boston Celtics are trying (rather aggressively, if you believe the rumors) to acquire Chris Paul. But I believe there must be something bigger at play, something bigger even than Chris Paul, even if that “something bigger” seems far-fetched and improbable and very much Dwight Howard.

On the surface, trading Rajon Rondo for Chris Paul does not make sense. I certainly believe the Celtics would make the deal — making a trade to upgrade a position normally makes a whole lot of sense, especially when the upgrade doubles as the world’s best point guard — but it’s impossible to ignore the element of selling Paul on Boston, since he would need to sign an extension with the C’s to make any deal feasible. That means Danny Ainge would need to sell Paul on Boston’s murky future, a future that (right now, at least) involves rebuilding with a relatively bare cupboard, or a cupboard that might include Glen Davis and/or Jeff Green as cornerstones. Ainge might as well try selling hair gel to Ray Allen.

Yet there are so many rumors there has to be some truth. Sam Amick says Ainge is “highly motivated” to obtain Paul. Adrian Wojnarowski reports the Celtics are looking for a third team (possibly the Indiana Pacers) to make the trade more doable. John Hollinger listed Boston as one of Paul’s most likely destinations. Where there is smoke, there is normally fire, and in this case, it seems the flames are growing large enough to engulf an entire city. It’s safe to assume that Ainge is desperately (or at least quite actively) pursuing Chris Paul. Which again begs the question: How will Ainge convince Paul to sign an extension with Boston?

He won’t convince Paul by hyping the weather, unless Paul enjoys winter mittens and snow storms. He won’t convince Paul by waxing poetically about Boston’s future prospects, unless Paul enjoys the stench of uncertainty. He might try convincing Paul by selling Doc Rivers’ new five-year contract, but even Doc’s sterling reputation as a players’ coach probably isn’t enough to overturn the pulls currently working against Boston, pulls that have always precluded Boston from signing superstar free agents in the past. No, if Ainge sells Chris Paul on Boston, he is selling him on a complete vision for the future, one that would need to include Doc Rivers, All-Star teammates and, most importantly, the ability to compete for championships every season.

Ainge must be trying to acquire Paul, then turn around and swipe Dwight Howard from Orlando. There’s no other explanation I can think of that could lead to Paul landing in Boston, or at least no explanation that makes sense. The possibility of teaming with Howard is the only sweetener that would make Boston appetizing enough for Paul to consider overlooking his reported love affair with Carmelo Anthony and New York City. I understand fully I probably sound like an irrational, overly optimistic fan boy right now — “AHHHH!!! CHRIS PAUL AND DWIGHT HOWARD!!!!!!” But is there anything else that could make Paul consider committing to Boston long-term?

There are ways teaming them both together is possible. If the Celtics trade Rondo for Paul, they will still have assets (namely: two 2012 draft picks, sign-and-trade rights to Glen Davis and Jeff Green, and a slew of expiring contracts) to throw at Orlando. That doesn’t mean any of these acquisitions are probable: more likely, Ainge swings and misses on Paul, Howard goes to the Lakers and Ainge goes back to wishing he never traded for Jeff Green. But turning a pu-pu platter into Ray Allen and Kevin Garnett (and ultimately a 17th banner) didn’t seem probable either. Anything is possible.

Trading for Chris Paul alone just doesn’t make sense. Ainge is planning a coup to extend Boston’s window of opportunity indefinitely. Let’s just hope it works out like 2007.

Now that a missed season is a real possibility, the lockout could end the Boston Celtics’ Big Three era. It could potentially threaten Kevin Garnett’s career. It could mean that Ray Allen is 37 years old when the NBA returns, and Paul Pierce might be 35. And if all that’s not enough, a missed season could result in Danny Ainge scrambling to fill 12 roster spots for 2012-13. I don’t mean to exude pessimism, but these are now realistic possibilities.

“There will ultimately be a new collective bargaining agreement,” NBA Commissioner David Stern said after hearing of the NBPA’s decision. “But the 2011-2012 season is now in jeopardy.”

And for veteran teams that have few bodies under contract right now, like the Celtics, they could very well fall under the category of collateral damage associated with this lockout if it wipes out the entire season.

Beyond 2011-12, the Celtics only have three players under contract – Paul Pierce, Rajon Rondo and Avery Bradley.

So if the season were to be wiped out entirely, the C’s would have as many as 12 roster spots to fill.

The Miami Heat certainly didn’t complain after needing to fill 12 roster spots last summer. But there were extenuating circumstances. Two of the game’s biggest stars (and Chris Bosh) were all free agents at the same time. The trio decided to combine their powers. It was a combination of luck, circumstance and the persuasive powers of Pat Riley (not to mention the persuasive powers of South Beach).

The Celtics wouldn’t be so lucky. Even if the free agency classes of 2011 and 2012 were combined, which is what would happen after a missed season, there’s STILL not the type of star power to rebuild on the fly. Dwight Howard, Chris Paul and Deron Williams are the only superstars on the market. Two of them play Rondo’s position. The other, Howard, will have many other realistic suitors besides the Celtics. If Howard did sign with the Celtics, the Celtics could presumably re-sign Allen and Garnett to smaller contracts and join them with Pierce, Rondo and Howard to form an awesome starting five. But that’s assuming Howard signs. And the Boston Celtics historically don’t land high-profile free agents.

More likely, the Celtics are looking at a lengthy rebuilding process after the (rumored) 2011-12 season. The thought is sobering, but it’s reality. The final year of the Big Three era is in jeopardy, and the future is unknown.

A month to play, and the Red Sox led the Rays by nine games. The Sox couldn’t lose.

Three games to play, headed to Baltimore for a three-game set while the Rays prepared for the Yanks, still ahead by a game. The Sox couldn’t lose.

Tampa down seven runs in the season’s final game heading into the eighth inning, the Sox ahead by one run in a rain delay during the seventh. The Sox couldn’t lose.

Tampa came back, tied the game 7-7 on a home run while down to their last strike, but at least the Sox were still ahead by one, Papelbon on the mound. The Sox could lose, but it was still improbable.

Papelbon worked Baltimore to their last strike, with some Oriole named Nolan Reimold — he of the .246 batting average and warning track power — at the plate. Meanwhile, in Florida, the Rays were still tied with the Yankees in extra innings. Once again, the Sox couldn’t lose.

But they did.

Is there a Celtics equivalent to blowing a nine-game lead in the season’s final month, coughing up a one-game lead during a three-game series against the Baltimore friggin’ Orioles, giving away a ninth-inning lead in a must-win game, a pack of gutless, more-than-well-compensated players playing each game with the intensity of a grandmother knitting a yarn scarf, and meanwhile, Tampa Bay comes back from seven runs down and wins on a walkoff home run in the twelfth?

Probably not, mostly because eight teams make the playoffs in the NBA, but let me try. For the purposes of this exercise, I am throwing out all limitations, such as a salary cap or even common sense.

The Celtics spend the offseason bulking up their roster with big names. They sign Jeff Green (let’s call him Carl Crawford) and Dwight Howard (let’s call him Adrian Gonzalez), entering the season with a Rondo-Allen-Pierce-Garnett-Howard-Green top six that everyone instantly hails “the best lineup ever.”

And then the Celtics start the season 1-7. Jeff “Carl Crawford” Green struggles in his new role and WEEI callers compare him to The Tin Man from Wizard of Oz — no heart. Howard is dominant as usual, at least defensively, but the mainstays — the Fantastic Four — struggle to regain their past magic. It’s as if they’re getting old or something. Everyone begins to jump off the bandwagon… just in time for the Celtics to start playing like the best team in basketball.

For the next three quarters of the season, the Celtics become who we thought they were. Howard swats shots into the fifteenth row. Garnett screams gutturally after every win. Rondo handles the passing, Pierce and Allen handle the scoring, and, well Jeff Green is still doing his best impersonation of The Tin Man. The Celtics enter the final month of the season (12 games remaining) ahead by seven games for the eighth and final playoff spot (remember, this is just an excercise, so pretend they could play like the best team in basketball for three-quarters of the season and still be that close to missing the playoffs).

Suddenly, everything goes wrong. Rondo starts throwing passes into Mark Wahlberg’s courtside seat. Allen gets hurt. Pierce doesn’t seem like he cares very much. Howard smiles too often. Garnett, who we’ll now call Dustin Pedroia, is the only player who acts like he still gives a damn. The ship is sinking and Jeff Green is still coming off the bench, a painful reminder of everything that wasn’t supposed to go wrong. Meanwhile, the Philadelphia 76ers won’t lose a goddamn game and Boston’s seven-game lead isn’t dwindling — it’s being thrown off the Empire State Building and free-falling until it reaches a painful death.

The Celtics are still tied going into the season’s last day. Their opponent is the Minnesota Timberwolves. The 76ers are playing the Lakers, but the Lakers have clinched the West’s top seed and will rest their biggest assholes… err, I mean their biggest stars. Boston trades for Travis “Bruce Chen” Outlaw in case they need some help in a possible one-game playoff.

But it doesn’t look like they’ll need Outlaw. The Lakers jump to a 25-point lead against Philly and maintain it into the fourth-quarter. The Celtics, meanwhile, build a five-point lead against the Wolves. Even though it’s not a huge lead, they seem to have control of the game.

And then hell has its first snowstorm. Andre Iguodala hits two four-point plays. Lou Williams cannot miss. Thaddeus Young dunks on Luke Walton’s head (remember, the Lakers are playing their scrubs). When Iggy scores five points in less than twenty seconds, the 76ers are down only three points with ten seconds to play.

Meanwhile, Boston’s lead is maintaining. But they are missing opportunities to put the game away — or, as my fifth-grade baseball coach used to say, to close the damn door. Garnett misses some bunnies. Howard slams a dunk into the back rim. Rondo misses free throws (surprise, surprise). Pierce’s month-long fog still hasn’t lifted. And Green sits on the bench, where he will stay unless a starter fouls out. With twenty-five seconds left, Boston’s lead is still four. No need for a fire alarm yet.

But the 76ers pull a miracle from their behinds. The Lakers miss two free throws that would have sealed the game (for some reason, we’ll call it “trying to sabotage another team’s season”, Steve Blake shoot both free throws with a blindfold on) and Philly gets one more chance to tie. Iguodala is not a fan of the three-point arc, but he drains one at the buzzer, sending Philly fans into a seizure of celebration.

Then the Celtics surrender a bucket to Ricky Rubio, who scores approximately one bucket every ten games. He’s fouled, too, by Ray Allen, and it’s Allen’s sixth. That means The Tin Man enters the game. Celtics fans everywhere hold their breath. Rubio cans the free throw, cutting the Celtics lead to one with nine seconds left. Michael Beasley steals the ensuing inbounds pass. As time runs out on the clock, he drills a three-pointer while Jeff Green, who was supposed to guard Beasley, saunters after him like a high school bully who enjoys being late to class.

Before the Red Sox can even say “what the fuck just happened?”, Iguodala dunks home a Lou Williams miss as time expires to send Philly into the playoffs. Dwight Howard says something about how “it wasn’t God’s plan” for the Celtics to make the playoffs this season, and millions of viewers think to themselves, “yeah, I imagine God spends most of his time worrying about who gets the 8th seed in the NBA’s Eastern Conference.”

There is good news for the Celtics, though: they still have The Tin Man under contract for six years and $120 million.

Thank God this is only a hypothetical, huh?

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?

As A. Sherrod Blakely writes on CSNNE, a season-erasing lockout could improve Boston’s chances of acquiring Dwight Howard.

Blakely’s reasoning is simple: if the lockout is lifted, Orlando could very well trade Howard. He does not seem intent on staying in Orlando, so the Magic’s best bet could be to trade him to the highest bidder before Howard departs for nothing in free agency. If the Magic do trade Howard, the Celtics, with limited assets, almost definitely could not make the highest bid.

On the other hand, if the lockout does wipe out the entire season, Howard could opt out of his contract and become a free agent. Then, Boston’s lack of trade assets would not matter and the cap space they have built would.

Of course, the Celtics would love to acquire Howard. Any team with a GM (not even any team with a competent GM; just any team that has a GM) would love to add the NBA’s best center. The problem is that Boston adding him, while not completely impossible, seems entirely far-fetched.

Reason #1:

When’s the last time the Celtics signed a superstar free agent in his prime?

(Waits for answer.)

(Still waiting.)

(No, Rasheed Wallace doesn’t count.)

(No, Shaq’s decomposed body doesn’t count.)

(No, Patrick O’Bryant doesn’t count.)

Do you give up? That’s because the answer is never. The Celtics traded for Kevin Garnett and Ray Allen, drafted Paul Pierce and Rajon Rondo. They drafted Bill Russell, Bob Cousy, John Havlicek, Dave Cowens, Larry Bird, Bill Walton and even Danny Ainge. They traded for Kevin McHale, Robert Parish, and even Dennis Johnson.

Players have consistently spurned Boston in free agency for at least two reasons:

1) The city has a reputation for racism dating back to the Russell era (and beyond). As much as Russell did for the Boston Celtics—I would never say a bad word about his contributions to the franchise—his comment calling Boston a “flea market of racism” stuck. He was the NBA’s best winner, yet a group of Boston morons had broken into his house, left racist graffiti on his walls, vandalized his trophies and poo’ed on his beds. The city deserved Russell’s harsh criticism. But his words certainly did nothing to improve Boston’s odds of signing a premier free agent.

A “flea market of racism” reputation doesn’t go away easily, although Kevin Garnett might have finally changed it. Garnett, at least according to reports, initially did not want a trade to Boston. He worried about the city’s attitude. He wondered whether the city was still a cesspool of bigotry. But Paul Pierce and Doc Rivers convinced Garnett to give Boston a chance. The city has changed, they said. And it has embraced Garnett with open arms, just like James Posey did so many times.

With Doc Rivers signed for the next five years and the local reputation changing, the Celtics could become a more desirable location for black players. But still, the next superstar free agent the Celtics sign will be the first.

2) Boston is cold, and it isn’t New York. Players will always want to play in New York City. The media spotlight shines brighter there than anywhere else. It’s the biggest market in the country, “the Mecca of basketball,” yada yada yada. Players can bear the snow when it comes alongside endorsement deals, fan support, basketball history (not so much professional basketball history, but still) and more attention than players could receive anywhere else.

Boston’s a big market, too, but it isn’t New York. And given the choice between living in South Beach or Southie, the white sand, mid-90s weather and zany nightlife sound pretty good.

Reason #2:

Yes, the Celtics could have miles of cap space for next season. Yes, Rajon Rondo will wear Green and White for the foreseeable future. But the Celtics’ future is murky.

Consider this: the Celtics have two players signed for the 2012-13 season. Just two. One is Rondo, who is an All-Star but probably not the type of free agent drawing card Chris Paul should be. Why not? There are serious questions about Rondo’s game. He can’t shoot. He disappears occasionally during the regular season, if not the playoffs. He battled nagging injuries, including plantar fasciitis, all last season; the injuries (and maybe a laissez-faire attitude toward the regular season) derailed what had been a Stockton-iffic start and left Rondo average for the final quarter (at least) of the regular season. Playing alongside Rondo would presumably be oodles of fun. But teaming with him is not necessarily a free ride to the NBA Finals.

The other player Boston has under contract for 2012-13, Paul Pierce, will turn 35 before playing a single game that season. If a free agent (such as Howard) is looking to build a Super-team, the Celtics won’t be his best bet—especially considering he could move to New York, play in the Mecca of Basketball, and call both Amare Stoudemire and Carmelo Anthony his teammates. Or he could move to Los Angeles and take over Hollywood. Or he could move to wherever Chris Paul lands and immediately field a better roster than Boston’s, even if the supporting cast couldn’t throw the basketball into an ocean.

Let’s say Kevin Garnett and Ray Allen decide to return to Boston for significantly smaller contracts. Even then, joining the Celtics would not guarantee competing for a title. Garnett will be 36 years old by then and Allen will be 37. If they’re still good players, they certainly won’t be All-Stars.

Don’t misunderstand me—Boston has its draws. Any superstar would love to play for Rivers. The franchise (mostly) knows what it’s doing, and is committed to winning. Rondo can make basketball easy for his teammates. The owners are willing to spend cash. The franchise is the greatest in NBA history. The city loves sports. But there are reasons free agents have never picked Boston, and those reasons will not evade Dwight Howard.

The Celtics would be idiotic not to try adding Howard. Hell, I assume all thirty teams will submit trade proposals for Howard if he ever hits the trade market. But I wouldn’t count on Howard signing in Boston, even if the Celtics preserve all their cap space, even if this season ends with a lockout and Howard chooses to become a free agent. Call me a pessimist or call me a realist. I would vote the latter.

Nonetheless, I’m keeping my fingers crossed, holding my rosary beads and saying all my prayers. And I’m not even moderately religious.