Cashing in for a star: the curious parallels of the Celtics trade for KG and a potential deal for AD

“I mean…I want KG, but giving up Al Jefferson, Gerald Green and picks is too much. I’d rather win with our guys.”

That’s an exact post on a well-known basketball message board from 2007 when rumors broke that the Boston Celtics were considering trading for Kevin Garnett. The author of that comment wasn’t alone. Multiple posters agreed with that line of thinking.

It’s an age-old dilemma, one that general managers and fans alike wrestle with: when do you push your chips forward and go all-in versus building with the kids you’ve drafted and developed internally?

In 2007, the Celtics were in a very different place. At the 2006-2007 trade deadline, Boston started talking to Minnesota about Garnett. The Celtics were awful, ultimately finishing with the NBA’s second-worst record at 24-58. The Timberwolves weren’t much better, as they wrapped the year at 32-50. The prevailing thought was that Garnett had accomplished as much as he possibly could in Minnesota. A trade would be best for both Garnett and the Wolves. Garnett gets to win and Minnesota kicks off a rebuild around a monster package.

No trade came together pre-deadline. Boston already had their sights on a top-two pick in the draft and snagging Kevin Durant (Danny Ainge’s long-admitted top target in the 2007 NBA Draft). But the foundation was set. This is how trades work in the NBA. They don’t come together in a span of a few hours on Deadline Day. It is months of conversations that build a trade.

The draft lottery came and went and things couldn’t have gone worse for the Celtics. Three teams (Portland, Seattle and Atlanta) leapfrogged both Memphis and Boston and any shot at Durant was gone. But Ainge, who never has just one plan, turned his eyes back to another Kevin: the established one in Minnesota.

The rub? Garnett wasn’t initially agreeable to a trade to Boston. He had no interest in swapping the Wolves’ looming futility for the Celtics. Paul Pierce was coming off a season-ending foot injury and Boston was coming off one of the worst seasons in franchise history. The upside of that particular roster wasn’t appealing to a veteran like Garnett.

To get Garnett, Ainge had to take a multi-step approach. The first move was to deal the teams now far less-appealing fifth pick and a couple of contracts to Seattle for Ray Allen. Allen was coming off his own injury-plagued season and there were questions about how his ankles would hold up as he approached the twilight of his career. The next move was to guarantee that Paul Pierce wasn’t going anywhere. Ainge made it clear he was done with rebuilding.

Fast forward to July 31^st (the writer of this story got one heck of a birthday present that year!) and news broke that Boston was close to acquiring Garnett. Not only had Garnett agreed to waive his no-trade clause, but he was also going to sign an extension with the Celtics. The final sticking point? The trade package going back to Minnesota. And that’s where the comment leading this article came from.

Throughout the day--this was before Twitter--reports surfaced that Jefferson was not part of the trade package. Given Big Al’s progress as a young player for the Celtics, this was a welcomed development. Ultimately, those reports were erroneous and Jefferson, Green, some salary filler and a couple of picks were shipped off for Garnett. And we all know what happened next. The Celtics jelled quicker than anyone could have ever imagined and brought home the 17^th banner to Boston.

Why the history lesson? Because history appears poised to repeat itself, albeit with some tweaks. A dominant big man is on the trade market and the Celtics are positioned to trade for him. This time around, Boston isn’t in the midst of a rebuild. They’re already a contending team (this season’s ups and downs notwithstanding), but one big question is exactly the same: Is it better to build with the guys the Celtics have drafted or should Ainge push all-in again?

Photo by Maddie Meyer/Getty Images

The immediate reaction is to say, “it worked before, so do it again”, but that’s overly simplistic. First of all, Jefferson and Green, as wonderful as they were as young players, are nowhere near the level of Jayson Tatum and Jaylen Brown. Second, the hope was acquiring Garnett to team up with Pierce and Allen would make Boston a title contender. The Celtics, as they stand right now, are already championship material.

In many ways, it’s that second condition that makes this a much harder decision for Ainge. The KG trade had little downside for Ainge. He wasn’t as rock-solid in his job as he is now. There were legitimate questions of his ability to be the guy to lead Boston back to relevance. Swinging for the fences with Garnett would either make the Celtics a contender, or Ainge would get fired. If he didn’t make this trade, and the previous Allen deal, Pierce was probably leaving. That also probably gets Ainge fired.

A decade plus later, Ainge is as solid in his position as any general manager in sports. He doesn’t have to make a big splash for Davis to keep his job. But things are lining up in an eerily similar way, albeit with a longer time horizon. Let’s break it down.

In the summer of 2017, Ainge signed his veteran that he’s ready to build around in newly-signed Gordon Hayward. That’s his Pierce. Hayward isn’t a Celtics legend or anything, but he’s an All-Star level two-way wing like Pierce.

Next Ainge goes and acquires Kyrie Irving. That’s his Allen, a high-scoring, injury-prone guard. It’s not a perfect comparison, but it’s pretty close.

Now, does he complete the package with Davis? It’s probably going to take a couple of young talents (Tatum and Brown equal Jefferson and Green), a large expiring contract to make the money work (Al Horford equals Theo Ratliff), some salary filler and draft picks.

Should history repeat itself? That’s where the differences come into play in a major way. As noted above, Boston is already a contender without Davis. Tatum and Brown are far more established than Jefferson and Green were at the same point. And, again, Ainge doesn’t need to make a trade.

Unlike Allen, Irving is a pending free agent. He wants to win a title, and he wants to play with Davis, if possible. And despite Pierce coming back from injury like Hayward is, Pierce being out was more a product of the tank job than Hayward’s very real recovery. Horford isn’t exactly equal to Ratliff either. Horford is still a very productive player, where Ratliff was basically just a contract. Finally, the draft picks Boston would be giving up are potentially more valuable than the two they sent Minnesota.

So, back to the question: should Ainge do it again? Do you give up two promising young players and draft picks to acquire Davis? To answer that, you have to work through a few other questions first.

The first question: How does this impact re-signing Irving? Trading for Davis would go a long way towards convincing Irving to re-sign in Boston. That alone puts a big check in the “make the trade” box. Without Davis, Irving may re-sign anyway. With Davis, it’s probably a lock. Now, if Irving says he’s walking, it’s probably not worth making the Davis trade. This is similar to Boston not swinging the Garnett trade if Pierce wasn’t sticking around long-term.

The next question: is a remaining core of Irving, Davis, and Hayward enough to compete for a title? You’re banking on Hayward getting back to somewhere near his former level to believe that. That’s still a very open-ended question. The signs are there, but nothing should convince you that that is a certainty at this point.

The last, but most important question: can you really trade Tatum and Brown? Let’s dispense with the notion that Boston is getting Davis by only including one of them in the trade. It’s almost guaranteed to take both of them. New Orleans knows Ainge has been planning for at least a couple of years for this moment. The Pelicans also know that trading for Davis is paramount towards keeping Irving. And, it’s not like New Orleans doesn’t already have other suitors.

If trading for Davis means keeping Irving, that’s a yes. Can you complete for a title with Irving, Davis and Hayward? Probably. Veterans would sign up to fill out Boston’s rotation, just like they did after the Garnett trade. But this time around, it would come early enough in the summer that pickings won’t be so slim. With presumably this year’s draft picks involved, a trade for Davis would most likely be agreed upon before the late June draft and ahead of the start of free agency on July 1st.

It’s that last question that is the hardest to answer. Winning by developing your own homegrown talent is always the best feeling. Seeing guys like Pierce, Kendrick Perkins and Rajon Rondo grow into integral parts of a championship team was extremely satisfying. They were our guys, the ones we watched grow from interesting youngsters to champions. On a less-successful level, we got to watch Avery Bradley and Marcus Smart become important rotation pieces on some good teams. That always means a little more than when a free agent or player you trade for becomes a key cog in a winner.

Tatum and Brown are no different. Brown was drafted higher than most had him pegged. Ainge took a massive risk in trading away the first overall pick because he knew Tatum, his guy all along, would fall to him. Interestingly enough, Tatum and Brown are the byproducts of Ainge trading away Pierce and Garnett to Brooklyn. We’re seeing Tatum and Brown develop rapidly and that’s both awesome and satisfying.

So, you want to believe we can get there with Tatum and Brown leading the way. But on the other hand, we’re talking about Anthony Davis here. When motivated, he’s one of the top-five players in the NBA. He’s a dominant force on both ends of the floor. In many ways, AD is KG, a superstar who is sick of losing and ready for his title shot. Davis doesn’t have a no-trade clause like Garnett, but he might as well have one with his ability to be a free agent in 2020.

There isn’t a perfect answer. Maybe Irving re-signs no matter what. Maybe Hayward rounds back into form. Maybe Tatum and Brown each develop into All-Stars. All of those things, or at least two or three of them, would keep Boston as title contenders. But that’s a lot of maybes. Davis coming to the Celtics guarantees they are legit title contenders.

It’s hard to say goodbye to the potential of youth. If they blossom elsewhere, you wonder what could have been. But it worked out just fine for the Celtics the last time. And it can work out just fine again. As much as winning a title with “your guys” is the sweetest, winning a title period is pretty sweet no matter what. And in Boston, winning titles is all that matters. It doesn’t really matter how you get there, just that you get there.