We’ve been saying this all year—Dwight Howard should be playing for the Chicago Bulls. Not only would that give him the best opportunity to win a championship, but the Bulls could actually put together a package for Howard and the albatross contract of Hedo Turkoglu that no other team in the league could compete with.

It almost makes too much sense, yet when Chicago sources are asked about the Bulls acquiring Dwight, it gets shot down as not happening. Ken Berger of CBS Sports reported on Sunday that Orlando management would really love to engage Chicago in serious trade conversations because they’ve got so much more to offer than the teams on Howard’s “list,” but Dwight won’t commit to signing a long-term extension there. Coincidentally, that’s the same reason the Bulls aren’t overly interested.

But the question that’s hung over the rumor mills like an ominous thunderhead all season long is, why doesn’t Howard want to play in Chicago? He and Derrick Rose could win multiple championships together over the course of the next decade. Seriously, why isn’t this being discussed more seriously by both teams right now?

The answer is two-fold, really, and the first reason has to do with Dwight Howard’s desire to be “The Man” where ever he ends up. This isn’t necessarily a bad thing. In fact, it would be hypocritical of us as media to bash Howard for passing up a chance to play with Rose when we absolutely lambasted LeBron James for doing the exact same thing in the summer of 2010.

James was (and still is, on a daily basis) slammed for trying to ride the coattails of Dwyane Wade to a championship. We would’ve rather seen him try to win a championship on his own because, by our definition, that’s what real superstars do. Rose himself has received high praise for being exactly that kind of guy. So the fact that Howard wants to run his own team, lead it to a ring, and become the sports hero of his home city should actually be something we laud.

None of that is possible in the Windy City, though. Derrick Rose is the only player in the league who, when the starting lineups are run at home, is announced as being “from Chicago!” rather than a high school, university, or foreign country. The uproar that follows from the 23,000 United Center fans is so deafening you can hardly even hear the kid’s name. Howard would get his love there, too, but he’d never be the city’s darling. That’s going to be Derrick Rose for the next 10 years. At least.

The other reason Howard won’t end up with the Bulls is because of the way Chicago approaches the trade deadline. They aren’t aggressive. They really never have been, unless they were dumping guys. Ben Wallace, Drew Gooden, John Salmons—those are the kinds of deals that usually get done in Chicago come February because deadline deals in the past have been part of a larger rebuilding process. But opportunities in the past to make runs at Pau Gasol and Kevin Garnett never went down, largely due to the fact that John Paxson and Gar Forman are notorious for over-valuing their guys.

Of course now, with the best record in the NBA, they have reason to over-value their guys, and there’s a strong belief within the organization that wholesale changes aren’t necessary to beat Miami en route to a championship as early as this year. The reason they won’t go for Dwight is the same reason they won’t look for extra help at the two this deadline despite Rip Hamilton’s injury woes all season long—they don’t think they really need it.

And maybe they don’t. Maybe, conversely, Dwight Howard doesn’t need them. Maybe both entities are already on completely acceptable paths to championship glory sometime in the relatively immediate future, and three years down the road we’ll say they were right in how they handled the botching of a potentially beautiful marriage.

But doesn’t it seem like both sides would be better off if they just got together? Chicago has the assets—more than enough to grab Howard and still boast one of the deeper benches in the league—and D-Rose and D-Howard could surpass Miami’s own dynamic duo as the NBA’s best. Everything appears to be set up for this to happen.

It won’t, though. We can say it should until we’re blue (or red) in the face, but too many forces are moving against it. The trade deadline will have to be interesting in other ways, because the headline reading “Dwight Howard Traded to Chicago” isn’t happening. At least not this month.