Danny Ainge’s Perfect Trade May Never Come

Why can’t Danny Ainge get a deal done? In just over a week, the Celtics watched Jimmy Butler go to the Wolves and Paul George go to the Thunder, even though they could have put together much better offers, and had every reason to pull the trigger.

This is what Minnesota gave up for Butler:

• Kris Dunn, a 23-year-old rookie coming off of a terrible season
• Zach LaVine, coming off of a torn ACL
• The no. 7 pick in the 2017 draft

This is what Oklahoma City gave up for George:

• Victor Oladipo, a solid young player about to begin a four-year, $84 million contract
• Domantas Sabonis, a 21-year-old rookie who was one of the worst starters in the NBA

This is a partial list of the potential trade pieces the Celtics have, which doesn’t even count any of their top seven players in terms of minutes played this season:

• Jaylen Brown, the no. 3 pick in the 2016 draft
• Jayson Tatum, the no. 3 pick in the 2017 draft
• Guerschon Yabusele and Ante Zizic, first-round picks in the 2016 draft who had solid seasons overseas
• The unprotected Nets pick in 2018, which will likely be in the top five
• Either the Lakers pick in 2018, protected at no. 1 or outside of the top five, or the better of either the Kings or 76ers pick in 2019
• The Celtics’ first-round picks in 2018 and 2019
• The Clippers and Grizzlies first-round picks in 2019 (with high lottery protections on both)

Pick almost any three assets from the list above and you’ll have a package more appealing than what the Wolves or Thunder actually traded. Even if Chicago was higher on LaVine and Dunn than anyone else, or Indiana felt the same way about Oladipo and Sabonis, it’s almost impossible to believe they would have valued those guys higher than a package based around a potential top-five lottery pick. The Celtics could end up with a top-five pick in every draft for four straight years, plus a bunch of other interesting young players. Their refusal (or inability) to give up any of those players or picks doesn’t make much sense when you consider their situation.

The Celtics have a meeting with Gordon Hayward on Monday, and they can no longer sell him on potentially pairing him with either Butler or George. Boston would have needed to sign Hayward before making a trade for either star, but the Pacers could have waited a week before they dealt their franchise player if they thought they had a better offer from Boston in their back pocket. Instead, the Celtics will have to woo Hayward even though he’s not nearly enough to close the gap between them and the Cavs by himself. While the road to the NBA Finals is easier in the East than trying to get through all the superteams being built out West, the Heat can make the same pitch. Ainge better hope Hayward falls in love with his collection of young players and future draft picks in the same way he did, or his team will strike out in a crucial summer.

This is Boston’s last chance to make a big splash in free agency with this core. Isaiah Thomas, Avery Bradley, and Marcus Smart will be free agents next season, and they are all going to want big contracts. Thomas ($6 million) and Bradley ($8 million) are on two of the most team-friendly deals in the entire league, while Smart is still on his rookie contract. Add all three of their salaries up together and they still make less than Chandler Parsons. Pay them anywhere close to their market value and the Celtics will be over the cap with a group that lacks the pieces necessary to compete with the Cavs.

Let those guys walk for nothing and Boston is no longer nearly as appealing a destination for potential free agents. The window for the Celtics to contend for a championship in the near future may have already closed.

The strangest part about Ainge’s reluctance to trade for either Butler or George is how willing he was to gamble in the draft, when he stunned the rest of the league by trading down from no. 1 to no. 3. That’s not a deal most teams would ever make, much less in a year when the consensus top player available (Markelle Fultz) was widely seen as being much better than anyone else on the board. The predraft consensus is wrong all the time, so there’s a chance that Tatum becomes a better player than Fultz, but it was a very risky trade, even with the extra lottery pick the Celtics acquired from the 76ers.

It’s not like Ainge should have that much confidence in his ability to find young talent in the draft, either. His past nine first-round picks before this year’s draft are Brown, Yabusele, Zizic, Terry Rozier, R.J. Hunter, Marcus Smart, James Young, Jared Sullinger, and Fab Melo. While it’s still too early to evaluate the three players taken in 2016, there aren’t a lot of terribly inspiring choices among the rest of his selections in recent years.

Plan A for the Celtics is still signing Hayward, but if that doesn’t happen, Plan B is building around Brown and Tatum, two guys who won’t be in their prime until the early part of the next decade. They have plenty of potential, but both guys have holes in their game and there’s no guarantee that either becomes a star. The hard part for Boston fans is what could have been. The Celtics could have drafted Fultz, signed Hayward, and traded the rest of their assets for George. Instead, there’s a chance they come out of this summer without any of the three. While things could still work out for Boston, the pressure on Ainge is intensifying. Ainge’s mountain of assets is still a mountain of assets. For whatever reason, there is still no trade. He may still be waiting on the perfect one, but the perfect one might never come.