NBA Trade Deadline: Should The Chicago Bulls Have Gone After J.J. Redick? Carlos Boozer’s Contract Should Have Been Swapped for Andrea Bargnani? What Is Luol Deng’s Future?

Earlier this season, general manager Gar Forman was in the market for a taker for Carlos Boozer’s immense contract, as well as another shooter to shore up the Bulls poor three-point percentage. But the club may have missed out on both opportunities

The Bulls are ranked 24th from beyond the arc, and allowed Central Division rival Milwaukee to snag sharpshooter J.J. Redick on Thursday. The Indiana Pacers were also linked to Redick before the deadline. Chicago was clearly aware of Redick's value, after trying to pry him from Orlando Magic in 2010.

Averaging a career-high 15.1 points and nearly 40 percent from three over seven seasons with the Magic, Redick went to the Bucks, along with Gustavo Ayon and Ish Smith, in return for Doron Lamb, Tobias Harris, and Beno Udrih.

To be fair, the Magic reportedly coveted a young player, and got two in Lamb and Harris, and Udrih’s expiring $7.8 million contract.

Also the Bulls may have passed on Redick because he is looking for a long-term deal this summer, and Chicago does not have the cap room to re-sign him for several reasons.

The Bulls had very few young chips to offer, and the Magic were not a team interested in taking on Boozer’s contract, since they’re already hoarding cap space for the summer of 2014. Orlando has about $23 million committed to player contracts for the 2014-15 season, putting them more than $40 million below the expected cap that year.

Though he has career averages just under 17 points and 10 rebounds, moving Boozer and the two years and $32 million left on his deal is more important to Chicago’s long term plans, especially with forward Luol Deng. The Bulls leading scorer this season at 16.8 points per game, Deng is a free agent in 2014, and will command a top dollar deal. Unless they are willing to pay the astronomical luxury tax rates that kick in next season, the Bulls cannot afford to pay both Deng and Boozer.

Deng is currently the third highest paid player on the squad, and will command a raise considering his contributions on both ends of the court, and durability. Deng has played in 299 out of a possible 382 games since 2009, can guard either forward position, and is capable of help defense along the perimeter. In 2014, the Bulls have roughly $56 million in contracts for Derrick Rose, Boozer, Joakim Noah, and Taj Gibson. That leaves a maximum of 11 roster spots to fill with about $15 million, and Deng possibly on the outside looking in.

The Toronto Raptors were reportedly interested in sending off disappointing Italian forward Andrea Bargnani. The former No. 1 overall pick in the 2007 draft, hasn’t lived up to his lofty expectations, but his contract is far more reasonable than Boozer’s. Bargnani has two years and $23 million left on his deal, and could have potentially stretched defenses for Chicago guards like Richard Hamilton and eventually Rose to penetrate to the lane.

Ultimately the Bulls avoided paying Redick, but with Boozer's contract still on the books, may have missed an opportunity to keep Deng in the future.