Even if we spend virtually all season (and offseason) focusing on transactions, most NBA trades don't materialize until they absolutely have to. The deadline and the July flip-over of each new league year spur action, but teams generally hold off on big deals because the alternative, standing pat, is so much safer.

Sometimes, though, a little boldness is necessary.

All the trades here are designed to draw double takes. They involve big names, tough decisions and high stakes.

These are the deals that need to happen, even if the teams involved may not be quite ready to admit it.

Damian Lillard Finally Moves On

The Trade: Brooklyn Nets acquire Damian Lillard from the Portland Trail Blazers for Nic Claxton, Royce O'Neale, Spencer Dinwiddie, 2025 first-round pick (via Phoenix Suns), 2027 first-round pick (via Philadelphia 76ers), 2028 first-round pick (via Phoenix Suns), 2029 first-round pick (via Dallas Mavericks)

The Brooklyn Nets' experience with Kyrie Irving, James Harden and Kevin Durant shouldn't put them off chasing stars entirely, but it should have taught them to prioritize reliability in their pursuits. That makes Damian Lillard, so far a one-franchise player whose loyalty borders on superhuman, an intriguing change of pace.

Reports indicate the Nets at least have their antennae up on Dame.

"If Lillard and Portland decide a parting of ways is best for both sides, multiple NBA executives believe the Nets could be a suitor for the All-Star guard," per Michael Scotto of Hoopshype.

If the Blazers finally rebuild, they could do a lot worse than getting one of the league's best young bigs in Claxton, plus a pick haul that allows them to bet against the distant futures of three teams—Phoenix, Dallas and Philadelphia—with aging, potentially disgruntled and/or injury-hit stars.

Dinwiddie and O'Neale are starters on expiring deals the Blazers could flip for more draft equity, a key for a franchise that hasn't attracted free agents and must build through the lottery and trades.

The Nets should consider offering another pick or Dorian Finney-Smith instead of Claxton, whose defensive mobility and shot-blocking make him an ideal Lillard complement—the kind of difference-making center he's never really had in Portland.

Ben Simmons is another candidate to move (more on that later), but if the Nets used him as the main matching salary, their pick outlay would get prohibitively larger. The 2016 No. 1 selection may be at a point where teams would want assets attached to take on his salary.

It's never been wise to expect a Lillard move, and we've got more than a decade of evidence saying he prefers life in Portland. But Dame might enjoy a change of scenery in a big market with emerging star Mikal Bridges, a player for whom he's expressed public admiration.

O.G. Anunoby as a Lillard Appeasement Plan

The Trade: Portland Trail Blazers acquire O.G. Anunoby and Precious Achiuwa for Anfernee Simons and either a 2023 first-round pick or a 2026 first-round pick (top-four protected)

The Blazers have an alternative to the teardown we just suggested in the Dame-to-Nets section: They can take a major swing to improve the roster in the short term, hopefully giving Lillard no reason to offer the ultimatum he at least hinted could be coming when he told ESPN's Stephen A. Smith:

"It ain't a threat. I ain't gonna say I'm putting them on the clock. I'm just saying if those things can't be done—if we can't do something significant like that—then we won't have a chance to compete on that level. And then, not only will I have a decision to make, but I think the organization will, too. Because at that point, it's like, 'Are you gonna go young, or are we gonna get something done?'

Anunoby is among the most fearsome, versatile defenders in the game. A burly forward with long arms, the heft to guard bigs and the No. 3 defensive estimated plus/minus in the entire league, he'd surely get Portland out of the bottom five in defensive efficiency, where it's resided every year since 2019-20.

Capable of checking centers, Anunoby also held his assignments to the lowest points per play of any wing who covered at least 100 isolation possessions.

Achiuwa is a project, but he'd address the Blazers' lack of athleticism at the 5.

From Toronto's perspective, this is mainly about avoiding the cost of Anunoby's next contract, as he'll likely hit free agency in 2024 (player option for 2024-25), and adding a young playmaking guard in Simons, who could help get its half-court offense up to speed. The allure of either draft-pick option listed above should be more than enough to get the deal done from the Raptors' end.