Let's take a look at how the Portland Trail Blazers and Denver Nuggets did in their trade Thursday. Here's a breakdown of the deal:
Blazers get: Guard Arron Afflalo, forward Alonzo Gee
Nuggets get: Forwards Will Barton, Victor Claver and Thomas Robinson, lottery-protected 2016 first-round pick, second-round pick
Denver Nuggets: B
When the Nuggets reacquired Afflalo on the morning of last June's draft, they anticipated him being part of a team that could compete for a playoff spot in the Western Conference. For a variety of reasons too complicated to delve into here, that vision has failed to materialize and Denver is now in semi-rebuilding mode. (We'll know how seriously the Nuggets are rebuilding by the end of the day.)
Given Afflalo can opt out of his contract this summer, Denver needed to move him now to ensure getting value in return, and did well to hold out for a first-round pick -- the same kind of value the Nuggets gave up for Afflalo (in the form of wing Evan Fournier) eight months ago. Denver, which made two first-round picks last year, already has one coming from Memphis (most likely in 2017) and now fills in a gap with a second first-round pick for 2016. Although the Nuggets gave up a first-round pick to move JaVale McGee's contract, they've got plenty coming.
In the meantime, Denver can take a look at impending free agents Barton and Robinson to see if they could provide any value. There have been stretches where it appeared Barton might be Portland's long-term answer as a wing reserve, but he could never score efficiently enough to justify regular minutes (his true shooting percentage is .448 for his career, and a miserable .422 this season).
And Robinson is stuck between positions. He doesn't protect the basket well enough to play center full time, while failing to space the floor as a power forward. Still, Barton and Robinson helped the Blazers at times with their energy, particularly at home, and are ideal fits for the Nuggets' up-tempo system at altitude. If they can't contribute in Denver, it's probably never going to happen.
Portland Trail Blazers: B

In the midst of an arms race in the West, until this morning the Blazers were the only team between 2-6 in the conference whose roster was unchanged from the start of the season. Upgrades elsewhere forced Portland to make a move to keep up, and a wing reserve was the obvious target. The Blazers hoped C.J. McCollum would step into that role, but he's been too inconsistent offensively to lock it down.
Barton, Allen Crabbe and Dorell Wright all got turns, never providing Terry Stotts with a satisfying solution. Portland's wing problem was exacerbated by Nicolas Batum slumping as he plays through a sprained wrist. Because the other alternatives were so weak, the Blazers never had the luxury of giving Batum an extended break to rest. The addition of Afflalo makes that a possibility.
More likely, Portland will be able to cut Batum's minutes slightly, which might be necessary to find enough time for Afflalo. (He'll also play some of the minutes Steve Blake had been playing alongside Damian Lillard in a small backcourt.) Because he's primarily a shooting guard rather than a player who splits time at the wing spots, Afflalo isn't an ideal fit. But he and starting shooting guard Wesley Matthews are both physical enough to defend most small forwards, and I'd expect the Blazers to play them together for extended stretches when Batum is on the bench.
That's an interesting pairing because Matthews and Afflalo are probably each other's best comp in the league. They both love posting up (per Synergy Sports, they rank fourth and fifth in points scored off post-ups among guards this season) and are dangerous 3-point threats (Matthews 39.5 percent career, Afflalo 38.4 percent career, though just 33.7 percent his season).
The biggest statistical difference between Afflalo and Matthews is that Afflalo has tended to shoot more long 2s, and it will be interesting to see if that changes in Portland. That could boost Afflalo's true shooting percentage, which has been up and down over the course of his career. Beyond that, Afflalo has acquired a 3-and-D reputation without ever rating well defensively by most advanced stats. He ranks 53rd on defense among shooting guards in ESPN's real plus-minus this season (Matthews is 13th, and surprisingly McCollum ranks 12th). Despite his poor RPM, Afflalo is unquestionably an upgrade at a point where even a small one could be the difference between having home-court advantage in the first round or not.
If Afflalo's presence ultimately swings a playoff series, it's worth giving up a future first-round pick. That's the gamble the Blazers are taking, because they could lose Afflalo to free agency this summer. If Matthews, LaMarcus Aldridge and Robin Lopez re-sign, Portland will be butting up against the luxury tax, which could make paying Afflalo unjustifiable. For that matter, Afflalo might simply want to go somewhere else he could start. On the plus side, having Afflalo's Bird rights does give the Blazers some flexibility should Matthews leave via free agency.
I'd be curious to know which side insisted on a 2016 first-round pick (lottery protected in both 2016 and 2017, at which point it converts to second-round picks). The lottery protection limits Portland's downside risk, but their 2016 pick will probably be better than this year's, and trading a future pick means the Blazers won't be able to trade their 2017 first-rounder until after the 2016 draft. So their options will be somewhat limited in terms of trading picks going forward.