When you're a team 6.5 games out of the No. 8 seed in a conference where that No. 8 seed might finish the season below .500 and will be little more than ritual sacrifice to the eventual No. 1 seed, you've got to make that trade.
When you're a team whose best player, DeMar DeRozan, does almost nothing but score, but does that inefficiently and not even at an elite level, and you've recently agreed to pay that player an average salary of $10 million through 2016-17, you've absolutely got to pull a trade for a player who does almost nothing but score inefficiently and at a sub-elite level and who will make up to $19 million through 2015.
When you're a team reeling from a decision to pay a former No. 1 overall pick, Andrea Bargnani, $50 million over five years to provide sub-elite, inefficient scoring, the rebounding of a good shooting guard at the center position and some of the worst defense Europe has exported since the Tsar Tank, adding another cap-maiming inefficient one-trick scorer is just plain smart.
When you're a team that has spent some time recovering from the loss of a star talent, Chris Bosh, by dropping lottery picks on promising big men, and one of those big men, Ed Davis, actually begins showing promise, you should definitely trade him for a player that completely replicates the strengths and weaknesses of your two most highly-paid players, albeit at a different position. I mean, why have an inefficient, highly-paid scorer-and-nothing else at one position when you can have them at three positions?
When you have a moody point guard who has clashed with the coach at like 20 different NBA stops and could be gone at season's end, and might blow up a dozen more times during a quixotic "playoff chase," you should totally trade the team's only other starter-worthy point guard and roll the dice. YOLO.
Instead of using cap space or potential cap space to help account for the fact that your team is not a typical free agent destination despite being located in a gorgeous city with huge market potential, you should always try to blow that cap space on a player no one in the league thinks is remotely worth his cap hit. Preferably, use it on a player who was not likely worth the cap hit before a major shoulder injury and whose shooting efficiency has plummeted since coming back from that injury 18 months ago. Let other teams leverage cap space for draft picks, who can become high-value-per-dollar contributors for between four and eight years if you pick wisely. Let the Cleveland Cavaliers do that. Blech. So boring. You go after that real Moneyball market inefficiency: big-name sub-elite scorers making upwards of $16 million per year.
When you have some bad contracts and some expiring contracts, and you're taking on a really bad contract in a trade, don't give up your bad contracts. Give up your expiring contracts. Because if you don't trade those expiring contracts now, they'll ... well, they'll just expire. Poof. They're gone, leaving nothing but flexibility and opportunity. Raptors, kudos on keeping those bad contracts in this trade. Eventually, you may be able to pick up a blue-chip prospect by trading one of those bad contracts to ... the Raptors.
When your team is No. 12 in the NBA in offense and No. 26 in defense, the answer is always to try to add more offense. Especially if it is offense that seems a lot more effective than it actually is. And especially if your coach, Dwane Casey, seems aggravated on a consistent basis about the team's lack of defense.
When you're going to give up your first-round draft pick (via the Kyle Lowry trade) unless it is in the top three or from No. 15-30, and when you are closer to finishing the season with the third-best chance at a top three pick (three games away) than you are to finishing the season with the No. 15 pick (6.5 games away), you should definitely aim for the No. 15 pick, because if you fail, heck, you're only giving up the No. 12 or 13 or 14 pick. If you aim for a top-3 pick and fail, you're giving up the No. 4 or 5 pick, and that just makes you look foolish for trading a pick with those protections for a rental player in the first place. You must prevent your previous moves from looking worse in the long-term. Bryan Colangelo understands this.
Bryan Colangelo understands the NBA and how to build a winner. This is how. The Rudy Gay trade is now. All hail the Raptors.