A compass spun by chaos sometimes finds gold in gravity. Maybe that’s why Rob Pelinka now locks his telescope on Jrue Holiday. Freshly rerouted from Boston’s green dreams to Portland’s cautious rebuild, the two-time NBA champ now floats in trade limbo. Meanwhile, the Los Angeles Lakers are brewing something loud. There’s a quiet storm behind their front office doors as every move whispers ambition. And every rumor hums possibility. As for Holiday, he might just be the crescendo.

Holiday reportedly felt the sting when Boston shipped him to Portland like a late plot twist nobody saw coming. At 35, he deserves bright lights and deep playoff runs, not the slow burn of a rebuild. While the Trail Blazers polish their future, Holiday’s timeline screams now. And truth be told, he would rather chase banners than watch another lottery-bound experiment stumble through the wild wild West.

The real question here is whether the Trail Blazers have any reason to part ways with Jrue. The Trail Blazers gave up Anfernee Simons for the veteran guard, and now they welcome Damian Lillard back into the squad. Sure, Dame will most likely miss the 2025-26 season, but Jrue? He would be there!

“So if you were to tell me Jrue Holiday was somehow getting bought out and waived or whatever, absolutely go pick him up,” Trevor Lane told on Lakers Nation’s YouTube Live. “But from there, again, it really makes no sense for Portland to do that unless there’s something that I’m completely missing in this situation.” He also clarified: “In league circles, they mentioned Jrue Holiday as being a potential target for the Lakers. That doesn’t necessarily mean from within the Lakers, so let’s keep that in mind.”

Your emphasis should be on “Doesn’t necessarily mean from within the Lakers.” Why? Well, LA doesn’t have much to offer in return for Jrue. “As a trade target for Jrue Holiday—$32.4 million—you’re talking about stacking up Vando, stacking up Gabe, stacking up Maxi Kleber in order to go get something done. Maybe something like that at some point makes sense.”

To snag Jrue Holiday and his $32.4 million tag for 2025-26, the Lakers must juggle numbers like circus masters. Gabe Vincent brings $11 million per year, Jarred Vanderbilt adds $12 million, and Maxi Kleber chips in another $11 million since his move from Dallas in the Luka trade. Stack them together, and the math teeters near perfect.

From Portland’s perch, flipping Jrue Holiday for expiring contracts feels like trading gold for glitter. Sure, Gabe Vincent, Jarred Vanderbilt, and Maxi Kleber offer financial relief, but talent-wise, they pale next to a fully charged Holiday. Unless the Blazers wake up and choose chaos by tanking on purpose, tossing Jrue aside makes as much sense as benching Damian Lillard in crunch time.

Speaking of Dame, Portland just stitched him into their future and cashed in Anfernee Simons to get Holiday. That kind of commitment screams ambition, not surrender. Pulling a U-turn now to hoard flexibility feels like throwing your GPS out mid-drive. The math may check out, but the logic? Slippery. So yes, if they actually move Holiday, someone better double-check who’s steering the ship.

Yet even the most dazzling trade package carries a shadow. Medical flags wave. Flexibility shrinks. Draft picks vanish like coins in a wishing well. And still, the spotlight shifts to Rob Pelinka, master of calculated chaos. Because when legends like LeBron and Luka wait at the gates, hesitation feels louder than risk.

Is Rob Pelinka ready to take the risk for Jrue Holiday?

The simple answer might be yes. “From the Lakers’ side of things,” Lane continues, “what the Lakers have done historically, they just at the trade deadline had a player that they renounced the deal for, in Mark Williams, because of injury concerns. The Blazers just pulled stuff out of their trade package for Jrue Holiday because there were some things that came up on the medicals.”

The Lakers once bailed on a Mark Williams deal over medical red flags. Now Jrue Holiday’s name comes with similar scribbles on the chart. That alone casts doubt. Add the Portland Trail Blazers’ own hesitations, and the idea starts to wobble.

Besides, Jrue Holiday brings more than gold medals and hardwood scars. With LeBron James already synced from their 2024 Olympic run, chemistry blooms fast. Pair him with Marcus Smart and DeAndre Ayton, and the Lakers could build a defensive wall you cannot climb. Despite averaging just 11.1 points last season, Holiday’s six All-Defensive honors and elite metrics scream impact. Three seasons left. One mission clear. Purple and Gold want rings, not reruns.

Sometimes, chasing banners means playing with fire and dancing on balance sheets. Jrue Holiday offers grit, gold, and a whisper of glory. Portland may stall, LA may hesitate, but Pelinka stands at the edge of a legacy-defining leap. The question no longer asks if—it wonders when. And when the moment calls, champions either blink or break through.