Kyrie Irving trade shows why evaluating Danny Ainge is really damn hard

Danny Ainge endured the jokes. He wasn’t bothered by the calls for the Boston Celtics to finally “do something.” Over the past two seasons, Ainge has more closely resembled a dragon hoarding his great stockpiles of wealth than an NBA general manager. His passiveness was always tinged with possibility.

That hoard finally yielded a significant return: Kyrie Irving, dealt Tuesday for a package centered around Isaiah Thomas. Finally, Ainge made the blockbuster trade he had spent two years declining. He proved, at least, that he was capable of making such a deal.

Let’s go back to the beginning. It was three seasons ago — when the Celtics won 40 games with all sorts of valuable future draft picks coming their way — when the Boston rebuild became a national storyline. By deftly trading his 2008 championship team — first Kevin Garnett and Paul Pierce, then Rajon Rondo — Ainge turned the Celtics into team that would win the Eastern Conference last season.

And by owning two Nets picks as Brooklyn wallowed in basketball impotence, not to mention several others from various other transactions, Ainge created a pipeline of young assets in Boston even as they started winning more and more under new head coach Brad Stevens.

At the 2016 trade deadline, Ainge was “very close” to a major deal and didn’t make it. Those are his own words.

“One story I probably can share with you is, I can’t tell you the team or the name, but it was very close,” Ainge told reporters. “It was something that we had been deliberating on for two days straight. The other team was doing that. And we were wrapping ourselves around a big package to do a deal. At the very last minute, they just said they did not want to do it. They just backed out. It was a deal that was talked about, thought about, and that was probably the closest that we came.”

This may have been a potential trade for DeMarcus Cousins or another such star. Either way, according to Ainge, it simply fell through.

Boston pursued Kevin Durant in the 2016 offseason and, when missing him, signed Al Horford. Ainge hoped to pursue Russell Westbrook if he became available in a trade, but the point guard re-signed in Oklahoma City. The Celtics hadn’t cashed in their assets — drafting Jaylen Brown with the third-overall pick rather than using it as trade bait — but still had plenty coming in the future.

At the 2017 deadline last February, the Celtics were reportedly in trade talks about Jimmy Butler or Paul George, ultimately deciding to deal for neither. It seemed like both would have been available, but the asking price for either player — including the 2018 Brooklyn Nets pick that would end up in the Irving deal — was simply too steep at the time, at least in Ainge’s view.

At one point, it was even rumored that the inclusion of Terry Rozier — a decent but unspectacular young guard — was a sticking point for a trade falling through.

The Celtics boasted the first-overall pick (one Brooklyn had originally owned), but in the week leading up to the 2017 NBA Draft, they traded it. They received Philadelphia’s third-overall pick and a future selection in 2018 or 2019 that should fall in the lottery. The 76ers instead grabbed the draft’s most coveted prospect, Markelle Fultz.

We all knew Boston still held the upper hand, still boasting enough assets to make nearly any trade. That’s why it was amusing to see the team trade back for even more draft picks, even if it was a sound move otherwise. It seemed like Boston would never go for it and make a win-now move. Perhaps, in the Warriors-led league, that was a sound decision, but it didn’t stop the jokes, mine included. (Yes, the best part about being a blogger is shamelessly linking to your own tweets.)

But now we know what has happened ever since then: Ainge finally had enough. Gordon Hayward was signed first. Now the Irving trade happened, which cost Boston a potential high lottery pick, a decent young big man in Ante Zizic, an extremely good role player in Jae Crowder, and Isaiah Thomas, who is a slightly older, much shorter version of Irving.

Ainge put Boston into a position where those assets were all tradeable, and still the team still hasn’t expended everything yet.

Thomas had a legendary season last year, especially his postseason run. But his 5’9 stature was always something that hampered the Celtics’ defensive schemes, he’s a year away from needing a massive payday to retain him, he’s three years older than Irving, and he’s coming off a hip injury that could even keep him out to start next season. Those are clear reasons why Irving is an upgrade.

Boston could’ve drafted Fultz, traded for Paul George or Jimmy Butler, and still signed Hayward, though. They didn’t have to wait on Hayward, who presumably would have agreed to sign with them anyway.

Team building is a treacherous process filled with uncertainty. It’s always easier looking back than in the moment. Perhaps the Celtics’ best possible scenario might have passed them by, but even if it did, Irving is more than a reconciliation prize. He’s a young, absurdly talented offensive player who should thrive in Stevens’ system.

This all comes back on Ainge in strange ways. His early maneuvering for assets was considered genius, and his late-stage hoarding was criticized roundly. He ended up giving up more than anyone expected for Irving, even though Cleveland had little in way of leverage, and he didn’t deal for a Butler or George, two players who are arguably better players than Irving and much more important cogs for any modern roster.

On the other hand, Ainge still gave himself leeway to come out of this situation just fine. The Celtics still own their own pick, next year’s Lakers pick (if it falls second through fifth overall, which is very possible), and 2019 first-rounders from the Grizzlies and Clippers. They have two highly lauded young prospects in Jaylen Brown and Jayson Tatum, plus an assortment of lower-tier youngsters waiting in the wings.

Even if we decide the Cavaliers clearly won this trade — that Crowder inclusion, a move Ainge had to make in order for salary purposes, really hurts — the Celtics could probably still trade for, say, Anthony Davis, if he ever hit the trade market.

Ainge set himself up for spectacular success, so much that failing in a spot or two might not even cost him in the long run. That’s what makes grading any single move of his, without context, an impossible endeavor.