NBA silly season is upon us, with rumors flying left and right regardless of their validity. Thanks to numerous websites, you can put yourself in the position of Danny Ainge or any other GM in the NBA to figure out how you would build a championship contender. For the purposes of these 5 deals, I have used, a fantastic site which works out the salary cap for you and also gives an adjusted win/loss prediction so you can see how your moves impact the team.

  1. Celtics receive #8 pick (NYK); Knicks receive #14, #26 and #30 pick (BOS)

Admittedly, this is not a trade I came up with and maybe that’s why I’m not in love with the idea of it. However, any time you deal three first rounders it certainly qualifies as bold. So what would the potential payoff for the Celtics be? has Tyrese Haliburton (PG, 6’5”/185lbs) currently going to the Knicks with that pick. Haliburton is regarded by most as the #2 PG in the draft after LaMelo Ball, though some rank Killian Hayes as high as or higher than Haliburton. The Iowa State product is a well-rounded guard, who averaged 15.2/5.9/6.5 during his sophomore season. He could slide in nicely as a backcourt mate of Kemba Walker with Jaylen Brown being more of a natural 3. Or, he could be another bench option for the C’s and serve as their best 2nd-unit scoring option. CBS Sports meanwhile has the reigning Naismith Player of the Year, Obi Toppin, slipping to the 8-pick, a choice Kevin O’Conner of The Ringer also agrees with. Both could be instant-impact players for the Celtics, my only hesitation is that some insiders have argued the gap between 14-and-8 may not be that wide in this year’s draft, which makes trading away three 1st rounders to move up six slots a bit of a second guess.


  1. Celtics receive #2 pick (GS); Warriors receive Marcus Smart, #14 pick and #26 pick (BOS)

Again, not a deal that was conceived in the wonderfully beautiful mind of Mark Paulette, but an intriguing one nonetheless. My first question: is it enough to make the Warriors pull the trigger? Over the past few years I’ve done a full 180 on Smart and am now a card carrying member of his fan club, no matter how maddening he may be to watch at times. His impact on games is evident, though part of me thinks Celtics fans over-value the guy compared to the rest of the league. Remember, Smart signed a deal with the Celtics two years ago worth roughly $14mil per season. I think if other teams were standing by and ready to break the bank for him, Smart would’ve left town. The argument for Trader Danny to make is Smart could be the ‘cherry on top’ a Warriors team that is primed to compete again next season, while that 14th pick is good value for the depth in this class, as was mentioned in the previous deal. If the Celtics were to hop up to #2, they would be crazy not to take James Wiseman (C, 7’1”/237lbs). Talk about missing pieces, the Memphis big man is exactly what the Celtics need. Wiseman posted 19.7ppg/10.7rpg and 3.0 blocks per game (albeit briefly) for Penny Hardaway’s squad a year ago. Park him in the paint to go alongside Kemba, Brown, Hayward and Tatum and that is one dangerous starting-5. Boston could then use the $12.9mil in freed up cap space (from dealing Smart’s salary) to acquire two mid-level role players. The issue is, Wiseman is also the missing piece for Golden State, leading me to believe the Warriors would want significantly more than just Smart and the two picks.


  1. Celtics receive Andre Drummond and #5 pick (CLE); Cavaliers receive Gordon Hayward, #14, #26 and #30 pick (BOS)

This one may increasingly require a sign-and-trade involving Gordon Hayward as we sit here lessthan 48 hours before his extended opt-out deadline. But the deal could still be swung in one of two ways. Say Hayward opts-in, then you simply make the deal as is which would net the Celtics $5.4mil in cap space. That’s roughly the salary of a mid-level exception, which they could use to bolster the bench. As for the pieces they receive, Andre Drummond clogs the hole in the middle for Boston. He is a beast on the boards, having posted 17.7ppg last season while leading the NBA with 15.2rpg. It was his 3rd-consecutive year leading the league in rebounds per game and 4th in the last five years. With the 5th pick, the Celtics put themselves in a prime position to get any number of players. Toppin, Haliburton, Hayes, Isaac Okoro (SG-SF, 6’6”/215lbs) and Deni Avdija (SF, 6’9”/210lbs) would all be options that I could see playing 25+ minutes in next year’s rotation. For context, says this deal would add a projected three loses for the C’s, but hey, the need a big.

Things get a little trickier should Hayward opt-out. For argument’s sake, let’s say Hayward declines the $34.2mil player option in search of more years. The Celtics would need to ink Hayward to a deal worth at least $28.7mil for next season in order to take on Drummond’s contract, a $28.7mil player option which he signed this morning. The other option, of course, would be including more than just Hayward in the deal to make the money work. Including Vincent Poirier ($2.6mil) in the deal would somehow make it work. Don’t ask me how the NBA cap works because clearly I have no clue. I’m just relaying what the simulator tells me. The C’s would take on the leftover $1.1mil in cap hit, but the trade would be a success.


  1. Celtics receive Victor Oladipo and Myles Turner (IND); Pacers receive Gordon Hayward, Marcus Smart, #14 and #26 pick (BOS)

This deal may be the best hypothetical on the table for the Celtics. The Celtics would fill their biggest void through Myles Turner manning the paint, and receive an All-Star caliber player capable of averaging 20+ points per game in Oladipo. Meanwhile, Hayward returns home and the Pacers get two starters to pair with Malcolm Brogden and Domantas Sabonis, plus the #14 pick to acquire their missing role player. It’s a win-win for all involved and a change of scenery for two guys (Hayward and Oladipo) who according to reports may not be all that happy in their current location. Plus, despite losing the two best players in the deal, it would be a big boost to the Pacers, who currently own just one pick in tomorrow night’s draft - #54 in the 2nd round, six picks from the bottom. Note: says this deal would cost the C’s 15 wins and increase Indiana’s projection by 15 wins, but I don’t buy that for a second.

Now we have to sort out Hayward’s contract again. If he opts in to $34.2mil for next season, the deal would net the Celtics $8.6mil in cap space which they would need to invest in depth, as the deal would basically leave Boston with just a really good starting-5 and no bench.

If Hayward opts out, let’s use a 3yr/$75mil contract as the baseline for a sign-and-trade. Hayward gets more years, Indiana takes on a friendlier average annual value. The trade still works, the Celtics just take on $553,000 in cap space.


  1. Celtics receive James Harden (HOU) and Clint Capela (ATL); Rockets receive Gordon Hayward, Marcus Smart, Romeo Langford, #26 pick, #30 pick, 2021 first rounder (unprotected) and 2023 first rounder – lottery protected (BOS); Hawks receive Kemba Walker, Daniel Theis and #14 pick (BOS)

Okay, this one will take some sorting out. Firstly, why it works for everyone:

Celtics: Let’s acknowledge the obvious - yes, it’s a sellout. But the Celtics have one, count ‘em, one championship in the last 34 years. As crazy as it seems to say for a deal which would bring a 1st-ballot Hall of Famer to Boston, most importantly the Celtics would satisfy their need for a big man. Clint Capela is a name that had been linked to Boston over the previous couple of seasons before he was ultimately dealt to Atlanta last year. Harden to Boston may turn a lot of people off, but the guy is one of the purest scorers the game has ever seen. Yes, his style of play puts many to sleep, but if he’s willing to adapt ever so slightly to get that elusive ring, you’re bringing an all-time great to town. There’s an argument to be made that he would be the greatest player to wear Celtic green since Larry Bird. (I’m sorry green teamers, but he’s better than Paul Pierce, while Kevin Garnett and Ray Allen were both past their prime by the time they arrived). A starting-5 of Harden, Brown, Tatum, Capela and whoever you choose as #5 would be deadly if it worked out, which it could if you convince Harden that Boston is the better path to a title over Brooklyn. Speaking of rounding out that 5th spot, along with a few bench pieces, this move would net the Celtics $23.7mil in cap space. That’s more than enough money to go sign a Davis Bertans or Montrezl Harrell with, or spend the money on two-to-three role players.

Rockets: A team that is building for the future, Houston would get an All-Star in Hayward and an All-NBA defender + above-average player in Smart. If Russell Westbrook hangs around, you could do worse than start your team with that trio. Langford would be a solid bench option for the team, plus, following the Robert Covington-to-Portland deal, the Rockets would then possess EIGHT first round picks over the next three years to build their team-of-the-future with.

Hawks: Atlanta is a team that feels it can compete beginning this upcoming season and they have money to burn. Bringing Kemba and Theis aboard would cost the team $23.3mil in cap space, but they’re one of the few teams in the NBA that can afford such a move. It also gives the Hawks a 2nd 20+ppg scorer in the backcourt alongside Trey Young, a guard combo that few teams could rival. Atlanta also has size to burn, especially if they were to add Theis. John Collins is a force underneath and put up 21ppg/10rpg last season. Atlanta would nab Boston’s 14th pick, with which they could likely land a “3 and D” wing and they already possess the #6 pick in the draft. Add Toppin or Advija with that selection and you have a team ready to make its way into the Eastern Conference playoffs.

Note: This deal increases the Celtics’ projected win total by six and the Hawks’ projected win total by three. It decreases Houston’s win total by 12, but they’re firmly a team in rebuild mode anyways.

I know what you’re thinking. James Harden would ruin a Celtics team predicated on ball movement between Kemba, Brown and Tatum. Harden is infamous for holding the ball upwards of 20 seconds of the shot clock. He’s routinely averaged nine assists per game for the last several seasons, but that’s more a product of the ball always being in his hands. Despite the negatives, there is no doubt he is one of the most lethal scorers in NBA history, and his recent comments may signal he’s ready to change his ways. If Harden is truly “singularly focused” on being dealt to the Brooklyn Nets, then he’s well aware the ball will not be in his hands a majority of the time on a team with Kyrie Irving and Kevin Durant. If it means winning a championship, he should be able to adapt to Brown and Tatum as well. Remember, we’re talking bold moves here, and you’re not going to find a bolder move than this 3-team swap during this accelerated NBA off-season.

Adam Kaufman, the sports director at iHeart Media - Boston cluster, joined The Drive on Tuesday afternoon to discuss the myriad of routes Danny Ainge and the Celtics may take over the next 48 hours.


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