If Celtics never traded for Kyrie Irving, what would they look like now?

The acquisition of Kyrie Irving two years ago today was a turning point of sorts for what had been a superb Celtics rebuild. After years of selling high and buying low on player assets (Rajon Rondo, Jeff Green, Isaiah Thomas), Danny Ainge had successfully turned the franchise into one of the most appealing teams in the league just a few years after hitting the reset button with the Garnett/Pierce trade in 2013.

Two star free agents (Gordon Hayward, Al Horford) had picked Boston over their lifelong teams in 2016 and 2017 respectively, and Irving was the piece that was supposed to take Boston to the next level, both on the floor and attracting star power for the long-term.

The All-Star point guard failed on both those fronts in Boston thanks to injury, attitude and a host of other factors. We’ve covered those plenty. Ainge did an admirable job this offseason of recovering from Irving’s disastrous departure from a team-building standpoint, successfully landing an All-Star replacement in Kemba Walker, a bargain center in Enes Kanter and the beginnings of a promising rookie class. Yet, as optimism is prevalent around the organization in the wake of such a miserable year, it’s hard not to ignore the lack of talk about a Banner 18 heading into next season. It’s not that the Celtics aren’t working towards it, it’s that they are simply no longer in position to contend for it for the time being. 2020 was supposed to be the start of the Celtics new championship window. Now, it’s tough to see just when that window will open once more following subpar injury luck and asset management.

There have been a lot of mitigating factors that contributed to this reality (Hayward’s injury, a lack of chemistry last season). Still, most of the C’s current predicament can be traced back to two years ago when Ainge decided to cash in a number of key assets on Irving in a deal that some (including yours truly) thought was a risky gamble.

Instead of rehashing the past, it’s perhaps just as intriguing now to explore what could have been. What would the Celtics look like now if they had never pulled the trigger on Irving in the first place? Let’s examine the options that would have presented themselves in the interim, what the C’s could look like now and lessons learned on both sides of the coin.

The Celtics roster pre-Irving trade (August 2017)

Al Horford: $27.7 million
Jae Crowder: $6.8 million
Isaiah Thomas: $6.2 million
Jayson Tatum: $5.65 million
Marcus Morris: $5 million
Jaylen Brown: $4.96 million
Marcus Smart: $4.5 million
Guerschon Yabusele: $2.25 million
Terry Rozier: $1.99 million
Ante Zizic: $1.65 million
Semi Ojeleye: $1.34 million
Abdel Nader: $1.17 million

Not eligible to be traded until December 15, 2017
Gordon Hayward – $29.7 million
Aron Baynes – $4.3 million
Daniel Theis – $815,615

Key draft assets besides own picks: 2018 BKN pick, 2018 LAL/2019 SAC pick, 2019 LAC pick, 2019 MEM pick

The 2017-18 season

This was a very crowded depth chart at the time of the trade but that logjam would have been reduced thanks to Isaiah’s hip issues out of the gate. It’s fair to assume he would have missed half the season and would have played a reduced role whenever he did return to the floor due to the decreased production we saw in Cleveland and Los Angeles. A look at the hypothetical depth chart without him in the mix.

Depth chart:
PG: Smart, Larkin, Thomas (injured)
SG: Brown, Rozier
SF: Hayward, Tatum, Ojeleye
PF: Crowder, Morris, Theis, Yabusele
C: Horford, Baynes, Zizic

Three thoughts on how 2017-18 impacts trade assets

1. It’s fair to assume Tatum’s breakout rookie campaign may have been impeded if Crowder was still around at the start of the 2017-18 season. He clearly wasn’t a happy camper after Hayward signed and knew his role was going to be diminished. The C’s moved on from him before things got ugly from a locker room standpoint, a lesson they perhaps should have followed with last year’s personnel in hindsight.
2. The Nets pick lost value pretty quickly out of the gate in 2018: Brooklyn began the year 10-14 before eventually finishing with the eighth-worst record. This was still an impressive trade chip as 2018 continued but declined in value a bit from August 2017.
3. For the sake of this exercise, end-of-bench rookies (Ojeleye, Zizic) get very limited opportunity and don't build up any real trade value. Even a guy like Theis only finds himself getting spot minutes. Thomas simply becomes salary filler in any hypothetical trade due to his hip condition. Hayward is presumed healthy since Irving wasn't here to throw him that alley-oop.



Other trade opportunities

Blake Griffin

January 2018: The Clippers trade Blake Griffin, Brice Johnson and Willie Reed to the Detroit Pistons for Avery Bradley, Tobias Harris, Boban Marjanović, a 2018 1st round draft pick (Miles Bridges was later selected) and a 2019 2nd round draft pick (Jaylen Hands was later selected).

Why the Celtics wouldn’t have topped it: The Celtics would have easily had the assets to outbid the Pistons here but it’s highly unlikely they would have done so due to Griffin’s $29.7 million salary. Matching the money for Griffin’s deal in a trade would not have been realistic without including Horford or Hayward and moving either of those guys for Griffin would have been a step sideways as opposed to forward.



Kawhi Leonard

June 2018: Kawhi Leonard demands a trade from San Antonio. He’s eventually dealt to the Raptors with Danny Green for DeMar DeRozan, Jakob Poeltl and a 2019 first-round pick.

Why the Celtics would have topped it: Boston started inquiring on Leonard as early as the trade deadline in February 2018, according to multiple league sources. If they didn’t have Kyrie Irving at this point, the push would have been stronger than ever to land a third healthy star for Boston. Let’s assume that the Spurs don’t have the stomach to trade Leonard until the summer though when he officially demands a trade. At that point, Boston is in a far better position to offer the best package for the Spurs. They have the Brooklyn pick to dangle (No. 8 overall) and making the money work for Leonard (earning just $20.1 million) gets a lot easier with Crowder still available to include ($6.8 million). Any trade still may have hinged on Jaylen Brown’s inclusion but the C’s would probably have been more inclined to take that risk given the depth at the wing spot. The No. 8 pick or Brown along with an additional first-round pick/role players (Morris, Crowder, Rozier) is enough to outbid the Raptors’ eventual offer.

Hypothetical trade in June 2018: Brown, Crowder, Morris, Yabusele, 2019 Clippers pick, 2019 Celtics first-round pick for Leonard

Leftover draft assets after Leonard trade: Brooklyn pick (No. 8), 2019 Sacramento pick, Memphis pick, own pick

Would Leonard stay after his contract expired?

There’s no question that the 2018-19 Celtics are far better with Kawhi Leonard and what’s left over than what we saw last season. They perhaps would even be NBA champions if everything broke right. A look at that depth chart for the 2018-19 Celtics. Is this good enough to get out of the East (assuming a healthy Hayward)

PG: Smart (re-signed), Larkin, Thomas (re-sign to cheap deal while injured)
SG: Tatum, Rozier
SF: Hayward, No. 8 pick
PF: Leonard, Mid-level signing, Theis, Ojeleye
C: Horford, Baynes, Zizic

It’s easy to like that group in the East last year against everybody. The Bucks probably would be the toughest matchup again, but this would have had the potential to be one of the best defenses in the league with plenty of shotmaking late spread throughout the Tatum/Leonard/Hayward tandem.

Let’s assume that this group pulls it off thanks to all the Warriors injuries and wins the title. Does Leonard still say? It’s hard to declare yes after watching the Raptors do everything right with him and still see him flee to Los Angeles. The prestige of Boston and a team built to contend for the next decade may have been more appealing to Leonard than an aging Raptors roster but that might not have been enough to keep him from Los Angeles anyway. The fact remains that Leonard ditching Toronto this summer should make the Celtics’ brass sleep a little bit easier this summer amid their tough circumstances. If he had stayed in Toronto for the long-term, that’s a mistake that would have been front and center every season for the foreseeable future.

If Leonard ditches after a title, the C’s are pretty much in the same spot they are now, but without Brown. That’s a very worthy sacrifice given the championship reward but wouldn’t have put Boston in a better spot for beyond 2019.



What about other possible trades?

Jimmy Butler

November 2018: Sixers trade Dario Saric, Robert Covington and Jerryd Bayless for Jimmy Butler and Justin Patton.

Why the Celtics wouldn't have topped it: We can think about this hypothetical both in a Kawhi and non-Kawhi world. It’s safe to say the C’s don’t bring in another wing to mess with a Tatum/Kawhi/Hayward trio. However, if Leonard wasn’t landed in the first place, buying low on Butler would have been an option in fall of 2019. The money ($20.4 million) would have been easy to match but don't forget the C’s had passed down dealing for Butler once before when he was with the Bulls. The guess here is they would have done so again. The only upside of landing him as a flight risk? Him going to a destination that demands a sign-and-trade. The Sixers getting Josh Richardson for him this summer is a nice option that Boston did not receive for Butler.

Anthony Davis

July 2019: Pelicans trade Anthony Davis and Solomon Hill for Lonzo Ball, Brandon Ingram, Josh Hart and three first-round picks and two pick swaps

Why the Celtics could have topped it even after acquiring Leonard: This is the hypothetical that could have made things very interesting last trade deadline. If the Celtics never dealt for Irving, they would have not been limited in trading for Davis due to the Rose Rule. That means they would have had everything to offer at the trade deadline February 2019.

So let’s envision the scenario. The Celtics already have Leonard but decide they want to go for it all now with Davis. At this point, the Lakers wouldn't have had the No. 4 pick to dangle so the C's had prime position. There would have been enough leftover to make the deal for Boston (assuming Tatum was included), although the C's would have needed to overwhelm New Orleans to pull the trigger so quickly.

Hypothetical deal: Celtics trade Jayson Tatum, Marcus Smart (needed for money matching), Ante Zizic, the 2019 Kings first-round pick and two future first-round picks for Anthony Davis

(This is arguably an overpay but I weighed it towards Pelicans to make it more realistic). C's probably could have done this without including all the picks given Ainge's haggling ability).

Leftover draft assets: 2019 MEM pick

New depth chart for 2018-19 post-trade deadline with Davis and Leonard

PG: Rozier, Larkin, Thomas (rehabbing)
SG: Hayward, Buyout signing
SF: Leonard, No. 8 pick
PF: Davis, Anthony Tolliver, Ojeleye
C: Horford, Baynes, Theis

Analysis: This group would have a chance against the Warriors squad even if they were at full strength. The risk would have been enormous for Ainge to go all-in on a couple of flight risks in Leonard and Davis, but the lure of a long-term juggernaut may have worth the roll of the dice. Leonard still could have walked in 2019 but a returning group like this would have been the heavy favorites against any non-Golden State squad. They are still legitimate contenders for 2019-20 with Davis under contract for the final year of his deal even if Leonard walks. If Leonard stays? They are favorites for the foreseeable future.

Given the way this offseason played out, there would have never been a guarantee that Leonard and/or Davis would have stayed over the long-term. The players are calling the shots now more than ever and any of these deals would have involved significant risk, just like the Irving one did.

However, it’s fair to acknowledge that either of these stars would have made the C’s more realistic contenders than they ever were with Irving under contract. There is no guarantee that Leonard or Davis would have been in Boston for more than a year or two but both would have better gambles in the short term than Irving proved to be. Ultimately, Ainge bet on the wrong horse here and that’s a mistake that the Celtics will need years to build back from.