Portland trades Hassan Whiteside or Kent Bazemore
4. Portland trades Hassan Whiteside or Kent Bazemore, plus at least one asset (and additional money if needed) for one of: Kevin Love, Danilo Gallinari, Blake Griffin, Marc Gasol or Serge Ibaka
This is league's clearest win-now move. Portland will haggle hard over sweeteners, and they will need more of them for the high-wattage names on this list. Anfernee Simons is almost certainly off-limits. Zach Collins probably is too. That leaves Nassir Little, Gary Trent Jr. and Portland's future first-round picks.
Love has been mentioned most (guilty!), but Gallinari might be a cleaner fit. He's on an expiring deal, and more of a clear-cut power forward. Love lives between power forward and center. That flexibility is useful, especially as Jusuf Nurkic recovers from injury, but it could become awkward as Nurkic regains full health.
Portland wields the leverage of choice. The market could be flooded with rotation power forwards from blah teams: the three guys listed above; Marcus Morris and Bobby Portis; Davis Bertans; Jae Crowder; Marvin Williams; Nemanja Bjelica; Robert Covington; others. Why pay whatever Cleveland asks if you can get a decent player for much less?
Portland also surely wonders how many teams will really bid for Love. Houston will poke around, because that's what it does, but I'm not sure the Cavs are much interested in Eric Gordon and Clint Capela. Would a third team jump in? A swap centered on Love and Gordon Hayward makes some sense, but trading Hayward raises uncomfortable issues for Boston. His college coach wooed him in free agency, and then his leg snapped in half.
Cleveland would argue Love is flat better than almost every other available big, and anyone Portland will ever get in free agency. If the Blazers start slowly, they may not have the luxury of waiting for every option to become available. On the flip side, a team that knows it's a seller on the power forward market may want to jump on a good deal early -- before the market gets crowded.
Keep half an eye on Griffin. Detroit does not want to trade him. The Pistons are hell-bent on making the playoffs. Griffin is their star attraction. But if things go badly, teams will call. Griffin would be one of the few really good available players with a max-ish contract that isn't too short or too long.
Gasol and Ibaka are here in case Portland decides to pursue a center on an expiring contract.
The Blazers have the goods to make a second win-now trade if they want. You can build some intriguing deals with Memphis involving Iguodala and/or Crowder.