Boston Celtics: Silly Season, Jrue Holiday edition

It's silly season, so let's start with Jrue Holiday

🎥 The latest from Taylor Talks Celtics

My thoughts on the notion that Boston may need to attach draft picks to move on from Jrue Holiday.

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📰 My favorite coverage from around Celtics-verse on May 21

• Charting a path forward for the Celtics, John Karalis.

• What is post-viral syndrome? Explaining the illness that limited Kristaps Porziņģis in the NBA playoffs, Tess DeMeyer

• Four reasons to embrace the Celtics' upcoming season of uncertainty, Chris Forsberg

• The NBA Draft, in many ways, starts at No. 3, Jake Fischer (SteinLine)

• Boston Celtics face Kristaps Porzingis conundrum after lost year, Souichi Terada

✍️ Silly Season is here, let’s embrace it

On Monday, I noted that we would spend this week looking back at the season as a whole. I’ve spent the last two days with writer’s block. I’ve realized that looking back, and trying to grade a season where the team was rarely healthy, and the year ended in tough-to-swallow fashion, is not where my head is at right now.

I’m sure that as we hit the dead of summer, there will be plenty of time for “player grades” and “top moments” pieces. They’re always fun to write. Yet, right now, the media wheels are turning, and with them, rumors are flying out of the gate.

I’m trying to enjoy the moment. It’s been a couple of years since the Celtics’ name was floated around this early in silly season. Some of the discussions have made sense. It’s logical that Boston would want to duck the second apron, especially as they’re unlikely to be a contending team next season. However, some of the topics being talked about are mind-blowingly wild — and they’re fun for a whole different set of reasons.

So, I thought it would be an enjoyable exercise to rank some of the rumors/trade ideas/discussion points over the coming days.

That way, we can get deep into each talking point or rumor.

First up, the Texas connection...

Not so much of a report, but likely more of an educated guess. Still, this comes from Kurt Helin of NBC Sports. He notes how the San Antonio Spurs and Houston Rockets could be among the ‘teams to watch’ for Jrue Holiday, assuming he’s made available for a trade.

“With Boston likely trimming payroll this summer, look for a lot of interest from playoff teams in Jrue Holiday, an elite defensive guard who has helped the Bucks and Celtics win rings. The Rockets and Spurs might be teams to watch,” Helin reported.

🗣️ Adding Holiday feels like something the Rockets would explore. Ime Udoka is a defense-first type of coach. He would likely adore the physicality, versatility and production Holiday could provide to his rotation. Houston has the assets and the reasoning to pursue a potential deal. I think they’re a logical candidate to at least kick the tires on what a trade for Holiday would look like.

San Antonio feels a little less likely to me. Yes, they’re rapidly improving. And yes, they have all the pieces they could need for a trade. Yet, they’re probably another year or two away from being taken legitimately serious. Holiday is a win-now type of pick-up. I’m not saying they won’t show interest, or a move isn’t possible, I’m just not sure it fits the current timeline.

Some other teams I would expect to gauge Brad Stevens’ willingness to negotiate are the following:

Miami Heat

Holiday feels like an Erik Spoelstra guy for the same reason he feels like someone Udoka would covet. The only issue here is that Miami is short on tradable assets (that would make sense for the Celtics), and they’re multiple moves away from being among the contenders, even in a weakened Eastern Conference.

I’ve seen a few ideas that would send Terry Rozier and his expiring contract back to Boston. I get it. But I would respectfully decline an offer built around Rozier. There should be better packages out there. Stevens will know that, though.

Still, Miami is on the hunt for upgrades, and Holiday represents a solid improvement at a genuine area of need for the franchise. Riley also isn’t against adding aging talent, as he noted in a recent news conference.

“I think an aging great player, who may not be able to carry a team together, can rise to the occasion in the playoffs,” Riley said. “…I still think that an aging player can play. Look at LeBron [James]. I mean, look at these players. It’s incredible. Players like LeBron and others who have played into their mid to late 30s and produced at a high level can help teams win championships. You have to pick out the right one, but I’m not against that, no.”

I don’t have the Heat near the top of my “threats to acquire Holiday” list, but I’m not ruling them out, either.

LA Clippers

Ty Lue is another defensive mastermind. The Clippers feel like the logical landing spot for Holiday from a theoretical standpoint. They’ve been trying to win a championship for years now, but have consistently fallen short. They’re likely one piece away from taking the jump they need.

Enter Holiday. You know, the guy who was the missing piece on not one, but two different championship runs?

I’m not sure what a potential deal could look like, or if the Clippers could even piece one together. Nevertheless, a backcourt pairing of James Harden and Holiday, with Kawhi Leonard locking down the wing, would be a fearsome trio.

Steve Ballmer won’t be afraid of any potential tax implications or the associated costs either. He could lose $30 million down the back of his sofa and never notice it’s missing.

I’ve honestly got the Clippers as a dark horse to sneak in and strike a deal for Holiday.

Golden State Warriors

I believe that the Warriors' biggest issue is their lack of genuine size in the middle of the floor. However, Mike Dunleavy Jr. has appeared quite happy to ignore that gaping hole over the last few years, so suggesting that they pursue a guard like Holiday doesn’t feel too far-fetched.

Still, Holiday is the type of do-it-all talent the Warriors need. I’m not sure how they could add his salary to a cap sheet that already includes Stephen Curry, Draymond Green and Jimmy Butler. However, it’s clear Golden State is still one or two pieces away from where it wants to be, and Holiday would help bridge that gap.

Cleveland Cavaliers

The last one on my list. Darius Garland’s postseason struggles are becoming well-documented. His lack of physicality and defensive upside make him a risky partner for Donovan Mitchell once the playoffs roll around. Finding a way to swap out Garland for Holiday could be the move Cleveland needs to finally become a genuine contender of the first time since LeBron James swapped Cleveland for Hollywood.

“He (Garland) needs to get stronger so he can compete at the highest level,” Koby Altman said during a recent news conference. “It’s the same thing that [happened] with Stephen Curry. … Now, Steph is all-world. I’m not making that comparison. But Steph got stronger … over his years. He’s a different physical specimen than he was when he first started playing.”

Holiday has the IQ and processing speed to fit into Kenny Atkinson’s system. However, I’m not sure if his motor is up to the task of consistently meeting Cleveland's tempo and pace.

🗣️ Holiday isn’t my preferred trade candidate

Holiday will turn 35 next season. He has three years left on his $134 million contract. I completely understand why his name is among the frontrunners to be removed from the Celtics roster.

However, I still think there are other moves to be made first. Kristaps Porzingis is by far the most tradeable guy under contract, in terms of the one you want to move on from. His inability to stay healthy and his Houdini act in two consecutive postseasons should be enough to convince Brad Stevens to cut bait.

Still, Holiday will hold value around the league. He’s a serial winner and could potentially embark on another championship run before his career comes to an end. And while I doubt that happens with Boston, I wouldn’t want to rush into moving him, at least not for pennies on the dollar.

🗣️ But I get it

What makes it more difficult is that Holiday wants to stick around.

“I think we still have a really, really great opportunity and a great window to be successful and win a championship again,” Holiday said. “I think the talent that we have on this team, not only on the court, but the coaching staff, all the way up to Brad [Stevens], has been amazing. So, yeah, the opportunity to win is now, and I still want to be a part of that.”

The problem is, outside of the final year in his current deal, Holiday’s trade market will likely never be as good. Maximizing your return has to be part of the decision making — as does ducking under the second luxury tax apron and accumulating some assets.

While it sucks to know that the current rotation will look different come October, it’s a tough fact that has been thrust upon us following Tatum’s gnarly injury. Hopefully, Holiday heads out West for a healthy trade return.

Where would you send him and what’s the minimum you would want back?