Celtics rebuild update: high ceilings or wider windows?

There’s this great paragraph in Keith’s analysis of the looming luxury tax and repeater tax that the Celtics will undoubtedly be facing if they choose to retain as much of their talented roster as financially possible:

The NBA is a time loop when it comes to managing a cap sheet. Someone always needs a new contract. There are options and guarantees and draft picks and everything else. Good teams have a long-range view, but you can only plan things out so far. Because of the nature of NBA deals, with no contracts longer than five years, things re-set fairly quickly.

Set aside for a second any concerns you might have of Wyc Grousbeck and the ownership group ponying up and paying to keep this squad together. He’s publicly stated that he’ll “pay for performance” and the goal is to raise more banners in the Garden. Frankly, as a fan, I’m not too concerned with whatever financial threshold they have set for themselves. It is what it is. From my perspective, I just want to win and maybe more importantly, win for a long time.

Our rival Lakers are currently scheming a way to cash in their chips after years of tanking to add soon-to-be 34-year-old LeBron James, Paul George, and Kawhi Leonard to build a superteam out West. It’s a get rich quick scheme that worked for Danny Ainge and the Celtics back in 2008 that produced arguably a 3-4 year championship window. As much as some of us love Al Jefferson and Gerald Green and first round picks, that’s a deal we’d make 10 out of 10 times. Maybe Danny Ainge learned from that desperate experience because ten years later, Ainge has been dealt dealt himself a better hand and could have his cake and eat it, too.

The domino effect of the Brooklyn trade and hiring Brad Stevens and transforming Isaiah Thomas and signing Al Horford and then later trading Isaiah Thomas for Kyrie Irving has brought the Celtics to a point where they virtually have two distinct cores with different age profiles. There’s the max money trio of Kyrie Irving, Gordon Hayward, and Al Horford who are 26, 28, and 32 respectively. There’s also the youthful nucleus of Jayson Tatum, Jaylen Brown, Terry Rozier, and Marcus Smart. Separately, they’re both legitimate starting points for a championship team to build on. Combined, you’re talking the potential of multiple banners.

Photo by Mitchell Leff/Getty Images

It’s an unprecedented embarrassment of riches. Never have two groups of All Stars and potential All Stars been separated by 3-5 years, roughly the length of an NBA contract. There lies the inherent issue. The lurking problem for Ainge is the progression of NBA star deals and the bittersweet number of stars that he could have on the roster.

At some point, these two Celtics paths will cross at the bottom line of the cap sheet and there’s just no realistic way--even with the deepest pockets--that Boston can retain 5-6 max players. As it stands right now, big decisions are looming over the subsequent summers:

• 2018: Marcus Smart RFA, Terry Rozier rookie extension
• 2019: Al Horford player option, Kyrie Irving player option, Terry Rozier restricted free agency
• 2020: Gordon Hayward player option, Jaylen Brown restricted free agency

It’s a minefield of potentially franchise-altering moves and it illustrates just how big these next few years are; it’s a two-year window where Danny Ainge could conceivably keep the band together in the immediate and retain all the talent. If you fell in love with this team this last season like I did, it means quite frankly that we should enjoy this unique situation next season and hopefully, the season after that.

David Butler II-USA TODAY Sports

We’ve seen dynasties built on younger stars teaming up with older stars. Magic Johnson and James Worthy joined a Lakers team with Kareem Abul-Jabbar and Jamaal Wilkes. The Anfernee Hardaway-Shaquille O’Neal Orlando Magic were lead by their two phenoms, but were buoyed by their veteran backbone. The Spurs, however, have been the benchmark of consistency by transitioning from (future) Hall of Famers David Robinson to Tim Duncan to Manu Ginobili to Tony Parker to Kawhi Leonard...but even the best have their issues.

With the Celtics primed and ready to make a run at Kawhi, the next two weeks will be filled with more leaks and more rumors. Trader Danny has a ruthless reputation of turning over players before their value takes a hit and it’s unclear how much he values Leonard. It’s been reported that Ainge made an offer to San Antonio at the trade deadline last season, but that was before Brown, Tatum, and Rozier almost carried the Hospital Celtics to the Finals. But remember: he didn’t wait until Kevin Garnett and Paul Pierce to retire in green. He exiled one of his favorite Celtics in Avery Bradley to Detroit before having to pay him as a free agent.

Ainge is keenly aware that it takes stars to raise banners. He raised #15 and #16 as a player alongside Larry Bird and put together the first Big Three to win #17. With a potential opportunity to acquire one of the top-5 players in the league just entering his prime, this could be one of those make or break moments for the Celtics’ GM. But the thing is, we’re not at that breaking point yet.

As former CelticsBlogger and current Ringer writer Kevin O’Connor points out,

These assets Boston has shouldn’t be undervalued either because of the fact that they’re cheap and they can get added on to everything else they already have. At some point, it’s going to get expensive for Boston and maybe you don’t want to get too expensive too early by dealing for Kawhi Leonard.”

Jeff has also advocated for the Celtics running it back. As much as we saw in 2017-2018, we just don’t know how good they’ll be with a healthy Kyrie and Hayward (and Daniel Theis) in the mix. Personally, the question shouldn’t be how high the ceiling could be with those players back or after a trade for Kawhi. The question should be how long of a championship window the Celtics can keep open. They have to trust the growth mindset that Brad Stevens has instilled into the franchise since Day One and while it might be tempting to jump the line, their patience will be rewarded in the end.