Heading into a bizarre offseason, the Boston Celtics are in a familiar position.
They couldn’t get past the Conference Finals and they have a raft of picks available to trade – this is a scenario Danny Ainge is used to, but will he take a different approach this time round?
Celtics trades are going to be one of the main features of the NBA rumour mill. With Marcus Smart pretty much untouchable, the salary of Gordon Hayward becomes Boston’s main trade piece (it’s almost inevitable he opts in). Ainge is loaded with picks to throw into deals, while Romeo Langford, Carsen Edwards and Grant Williams all have enough value to be useful.
If Ainge is happy to deal Hayward, options open up all over the league. One potential trade partner would be the Indiana Pacers, who finished just one spot behind the Celtics in the East last season.
An Oladipo trade is far from guaranteed. Indiana could keep the All-Star guard, try to compete in 2021 and re-evaluate his future at the trade deadline. With the current construction of their roster, they will want assets that can help them in the short-term, and that might work against Boston, who’s trade package will be built around picks rather than proven young talent.
The small-market Pacers could be motivated to move Oladipo to shed salary. Using Hayward in such a deal wouldn’t do that, but maybe the Celtics could help out by taking on Myles Turner’s remaining three years, too. It commits the Celtics to a hefty tax bill in the coming years (particularly if they re-sign Oladipo), but that’s the price of competing for a championship.
While there are suggestions the Celtics are happy with their centre rotation, their lack of size was an issue at times in the playoffs. Turner brings rim protection they lack from Daniel Theis and Enes Kanter, and he’s a versatile offensive player, capable of spreading the floor or rolling hard out of pick-and-roll sets.
The contract is sizeable at $18 million through the 2022/23 season. Indiana will want significant compensation for Turner, and they will be wary of getting less by packaging him with Oladipo.
Acquiring Oladipo is a risk, but the Celtics do not have roster space for all three of this year’s first-rounders as it stands. They already have long-term commitments to young players alongside Smart and Kemba Walker’s deals. If Oladipo cannot deliver or he wants to leave as a free agent, the Celtics are still in a great position with Tatum, Turner, Brown, Walker and Smart.
The feasibility of a Hayward for Oladipo and Turner deal obviously depends on what Indiana would want. This year’s three first round picks are unlikely to be enough. Do the Pacers go for it if Boston add Langford, Grant Williams or Edwards? Could another future Boston first get it over the line?
Once again, the Celtics are in prime position to make a major trade. There might be reluctance to move Hayward, who has been an important piece when available. With such persistent injury issues, though, Boston should be fine with using his salary to bring in two starter-level players in Oladipo and Turner.
It also depends on how the Pacers view Hayward. He could be a serviceable bridge in 2021, helping them win games as they re-tool the roster. He fits well under any coach and would be a good wing to have alongside Malcolm Brogdon and TJ Warren.
With how past offseasons have gone, this isn’t a deal any would expect Ainge to make. There’s a breaking point, of course, where a combination of first-round picks and young players would make the Celtics wonder if it’s worth it for Turner and potentially one year of Oladipo.
There are a lot of moves Boston can make with Hayward’s salary. This, if feasible, is the most interesting. As good as he’s been, as effective as he is at both ends, the Celtics must consider a Hayward trade this offseason – it’s their best route to improving the team significantly.