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CelticsBlog offseason roundtable: setting the table for the draft and free agency

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Three CelticsBlog contributors sat down to discuss all the factors that shape Danny Ainge’s options for improving the roster

Boston Celtics v Miami Heat - Game Six Photo by Jesse D. Garrabrant/NBAE via Getty Images

With the Lakers tying the Celtics with their 17th championship, it’s officially the offseason. With the NBA Draft set for November 18th and free agency to follow soon after, the Boston Celtics forge into what could be a very interesting fall. Facing a roster crunch and the salary cap tax threshold, Danny Ainge could choose to do very little, but with three first round draft picks and a handful of expiring contracts, he could get creative. We discuss.

Adam Spinella: Coming so close to another NBA Finals appearance this year leaves a lot of positive momentum for this Celtics team heading into next season. The championship window is officially open. As it pertains to the draft, Danny Ainge has three 1st round picks (14th, 26th, and 30th overall), as well as a mid-2nd rounder (47th) to add potential pieces. As we all know, rookies don’t generally play a large role on teams with championship aspirations, so there’s a bit of cognitive dissonance between where we have assets and how we improve.

Keith, help set the table for us. What cap implications and roster limitations surround the Celtics that might shape how they attack the draft and offseason as a whole?

Keith Smith: There are a couple of challenges facing the Celtics as far as roster-building for 2021 go. First, they are into the luxury tax. Pending further additions, that could end up being well into the luxury tax. while Danny Ainge acknowledged the team has planned to be in the tax, there are still limits. That could mean Boston looks for trades to get off some of their tax bill, by using a draft pick or two to dump salary.

Part of why that is seems plausible is roster spots. The Celtics already have nine players with fully guaranteed contracts for 2021. That number will increase to at least 12, because Daniel Theis isn’t going anywhere (he’s non-guaranteed as of now) and both Gordon Hayward and Enes Kanter are likely to pick up their player options. And that’s before you get to a few of the swing players or retaining any of their own free agents. Adding four more draft picks to the mix only makes that situation messier.

Do you guys agree that it’s unlikely Ainge uses all four of his picks on players likely to be in the NBA in 2021?

Boston Celtics Hold Introductory Press Conference For Draft Picks Photo by Suzanne Kreiter/The Boston Globe via Getty Images

Bill Sy: I’d say it’s very unlikely. As it stands, they’re ten deep—if we’re to believe that the Williamses and Langford are fixtures in the franchise’s future—and with the possible additions of a MLE and/or BAE addition, I doubt Ainge and Stevens sees the need to add another young player into the mix unless somebody absolutely blows them away at the back end of the lottery or mid-first round.

ADAM: Agreed. With the championship window open and so many young players on the fringes of the roster, there isn’t a ton of space left to take on developmental projects. As Keith mentioned, since the luxury tax looms large, there’s not much financial room to be creative with clearing room for more.

Another avenue to consider could be the “draft-and-stash” route, where Ainge picks an international prospect with one of their three first-round slots. By taking a guy who agrees to stay under contract overseas, it would buy the Celtics time without having to take pennies on the dollar when shopping their picks.

To me, this frames the conversation around the draft. They can’t keep all three picks. Do they go with a player who can help immediately at 14, then roll the dice with which draft-and-stash guys might be around later? Or is the more prudent strategy to look for a stash candidate early and hope to find the right picks for the roster later?

There is a third option, which is consolidation. Do either of you see trading a bundle of these picks together for a higher selection as a prudent course of action?

BILL: Well, did you guys listen to Simmons with Jackie Mac? She mentioned that the Eagle Tribune reported that LaMelo Ball had a private workout with the Celtics...

ADAM: I saw that, but to me it’s due diligence on the possibilities of trade-ups, not necessarily evidence of interest. This draft is, in terms of comparative perception, weak in terms of top-level talent. Teams looking to trade down from a top-five pick will eye the Celtics as a natural partner since we have three selections and a few other youngsters to offer.

Boston should conduct workouts and interviews with guys higher than their range just to see if they’re enamored by one enough to pull the trigger on a trade. But that doesn’t necessarily mean they should with so many other mouths to feed on the roster already.

KEITH: I could see Ainge trying to consolidate picks in an effort to move up. I could see him putting picks with players to get off salary. I could also see him consolidating picks with players to either move up or bring in a veteran that can help the team win now. I guess I can see just about anything!

My best guess is that Ainge uses one pick, flips one for a future pick and uses a third on a draft-and-stash player. Projecting big trades using draft picks is always a hard thing. I will say this: I expect Ainge to be active at the draft with trading picks, because he almost always is.

ADAM: And he has to be this year. What’s apparent is that, regardless of with what pick or how they acquire it, the Celtics could use some depth.

Three areas stand out as being places to address this offseason. One (in no particular order) is adding a little more shooting. We saw first-hand the value of 3-point threats in the series with the Miami Heat and what high-caliber role players do to bring out the best in their stars. With so much scoring artillery already in Beantown, perhaps a gravity-creator and someone who plays off our star power is a worthy addition.

Boston Celtics v Miami Heat - Game Six Photo by Fernando Medina/NBAE via Getty Images

Another is finding a backup point guard. Brad Wanamaker is a solid backup, but he’s a free agent and ran into moments this postseason where he didn’t quite provide enough. The injuries to Kemba Walker may have shown a necessity for one more handler and creator with the second unit.

Finally, Ainge has to find a way to solidify the backup center spot. Robert Williams and Grant Williams both play unique cogs in the machine, but neither are strong enough yet to be reliable in that role on a nightly basis. Kanter is likely to opt-in, but he’s only playable against certain playoff opponents. There are a ton of moving parts to consider.

How would you go about prioritizing those needs and balance addressing them via the draft or free agency?

BILL: Let me play devil’s advocate for a bit. Let’s say nothing changes. The top-6 come back plus Kanter picks up his option. If you believe Ainge and your eyes, the Williamses and Romeo Langford will get significant run next season. That’s ten players.

Chances are slim to me that Celtics can identity an immediate impact player from picks #10 to #25, but it’s possible. It’s more likely that they’ll shore up that positions of need through the MLE or BAE, right?

KEITH: I think the MLE is where an impact player comes from. It’ll likely be the taxpayer MLE, but that should be enough in a depressed market to get a quality free agent. It’s probably only going to be a for a year, with a second-year player option attached. But that’s OK. It’s fine to keep flexibility, especially with so many others on long-term deals.

I know Adam says center and point guard are key spots, and I don’t disagree. I think given the team’s injury history, another wing couldn’t hurt either.

Given all of that, who are some players you’d like to see Ainge target with the MLE of about $5.7M or so?

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BILL: I’m warming up to the idea of bringing in one of Jayson Tatum’s good friends, Harry Giles. There are established veterans that have a higher floor in terms of expected production like Serge Ibaka and Aron Baynes, but I’d like Ainge to try and thread two needles here: signing an impact player and looking for young players that are in Tatum and Brown’s age profile.

ADAM: Giles makes sense because he’s affordable, but to me his position is the one most easily replaced. There will be plenty of veteran big men on the free agent market who are a little more “plug and play”, so if there’s one role to most focus on filling via free agency, I’d expect there.

When looking at available bigs, I’d love to see Boston add a true stretch-5 to their lineup. Theis shot only 15.4% from 3-point range in the Playoffs. We saw first-hand the value a pick-and-pop big can have in the Toronto series, where Serge Ibaka was arguably their most consistent player. Perhaps the counter isn’t in finding a backup who can defend that role, but in who can execute it.

BILL: I’d caution using the small sample sizes of the playoffs, but yeah, having a reliable pick-and-pop big would be a great addition to Stevens’ tool chest, but isn’t Grant already that guy, though? I just don’t know if that makes the Celtics that much better.

Last summer, the addition of Kanter felt like a move to address Boston’s perceived rebounding issues, particularly after the losses of Al Horford and Aron Baynes. The team won’t have that level of attrition with the roster over the next two months, so I’m wondering if Ainge doesn’t target need so much as upside this offseason.

KEITH: I don’t know that Grant is as reliable as a shooter to quite count on him in that role yet. I think Ainge gave us a little bit of a hint during his postseason media availability when he said “Everyone says to draft the best player available, and sometimes you do that. But sometimes you draft for need, too.”

I wonder if this could be a draft where Ainge prioritizes need over best available.

Oh and count me in 100% on Harry Giles. I think his skill as a passer really fits. He’s also tight with Jayson Tatum, which can’t hurt at all either!

ADAM: Agree on Williams. He can be that small-ball 5 defensively, but his 3-point shooting demonstrated in the playoffs is a little smoke and mirrors. Just taking your advice on the small sample sizes of the playoffs, Bill.

Are there other free agent names you two are honing in on that might fit in the budget?

NBA: Atlanta Hawks at Boston Celtics Winslow Townson-USA TODAY Sports

KEITH: I think big-name guys like Davis Bertans and Derrick Favors will command far more than Boston can offer. And doing any kind of sign & trade deal gets tricky for the Celtics due to the hard cap they would then incur. I don’t know if Aron Baynes would be up for a return or not. If not, I would love to see what a guy like Alex Len (he shot more threes with Atlanta) or Bobby Portis could do in Brad Stevens’ system.

I’m also always going to advocate for a return of Isaiah Thomas off the bench. I think he would help quite a bit, assuming he’s healthy. Shooters like Kyle Korver or Pat Connaughton would be welcomed.

Mostly, I think what you see is what you get. I don’t know that any real impact free agents exist that are attainable for the Celtics.

BILL: Baynes would be a dream and I’d be pro-reunion with a bunch of former Celtics like Marcus Morris, Jae Crowder, Kelly Olynyk, Rajon Rondo, and Avery Bradley. I recently wrote about the need for the Celtics to embrace a youth movement, but for me, those guys will always have a parking space at TD Garden.

Regardless of what Boston can do with the MLE or vet minimums, they’ll still have three first round picks next month. I know it’s been nearly eight months since we’ve seen a lot of these players on the floor, but does anybody catch your eye as a possible target in the draft, Adam?

Boston Celtics v Washington Wizards Photo by G Fiume/Getty Images

ADAM: Don’t get me excited with the Isaiah talk like that, Keith. I’m ready to dust his t-shirt off in the drawer...

As I wrote about last week, the Celtics have three picks but cannot keep all three on their roster. Whether they make a deal or pick someone as a draft and stash prospect overseas, that thinking is going to shape their draft strategy. If they love one of the international guys like Theo Maledon, Aleksej Pokusevski or Leandro Bolmaro, they make snatch him up at 14, then have the flexibility to search for other help late in the first-round.

One frontcourt name I’ve loved for the Celtics at the 14th pick would be Jalen Smith out of Maryland. He’s a tailor-made pick & pop 5-man for the modern NBA who shot over 40% from 3 after January 1st, helping the Terps climb to the top of the Big Ten. He’s versatile enough defensively to switch or drop back to protect the rim, and athletically has enough upside to turn into a really interesting complimentary piece on offense. I’m a big Smith fan.

There are a few shooters who catch my eye but may not slide all the way down to when the Celtics pick at 26. Tyrell Terry of Stanford is a name gaining steam as he’s added weight and continues to grow, and has elite shooting chops for a guard. But he may not be ready to step in right away since he’s only 19. Cole Anthony may be best player available at 14 and fills the need for bench scoring. Shooters like Saddiq Bey or Aaron Nesmith fill roles too, though they don’t have the type of upside typical of a lottery pick.

We have to start with what gets done at 14, which will shape how the Celtics can really attack picks 26 and 30.

Maryland v LSU Photo by Sam Greenwood/Getty Images

BILL: I love that Jalen Smith pick, Adam. He’s a perfect fit in Boston, but to your point about how the Celtics approach #14 will affect how they look at #26 and #30 (and potentially trading up), I’ve seen him mocked anywhere between the backend of the lottery to a late-first rounder. I’ve always wondered how GM’s navigate the unknown like that...

One of you guys is going to convince me that Tyrese Maxey shouldn’t be a Celtic. Back up point guard could be a position of need if the Celtics opt to not bring back Brad Wanamaker and Maxey seems to have the profile of so many past Boston picks: undersized, questionable shooter, but is a solid defender and has a knack of coming up big in big moments.

KEITH: I’m at the point where I don’t think you can go wrong with drafting a Kentucky guard. I love Immanuel Quickley. He’s a great shooter, great rebounder for his position and a good defender. Cal really cranks out the guards year after year.

The other guy I think who could be in the mix if he drops enough is Cole Anthony. Highly rated high school star who struggled to shoot it as a freshman? Danny Ainge must be in love!

NCAA Basketball: Kentucky at Arkansas Nelson Chenault-USA TODAY Sports

ADAM: Both Maxey and Anthony are highly talented and in the mix at 14, but if we’re sizing up what position might have the most depth when the C’s are on the clock at 26 or 30, it’s definitely point guard. There are a few guys who look like capable second-unit creators to fill Wanamaker’s shoes, even as soon as next year.

Duke’s Tre Jones, San Diego State’s Malachi Flynn, Arizona’s Nico Mannion and the aforementioned Quickley could all be available. They all come with small warts (Jones with shooting, Flynn with size, Mannion with defense, Quickley with finishing), but if they didn’t, they wouldn’t be around at that point in the draft.

Another name I’d love to see Boston take a flier on is Isaiah Joe. The shooter from Arkansas doesn’t get mocked in the first-round frequently, but he could end up being the best shooter in this draft class. Long, wiry arms, deep range and a really solid team defender. He’s a gem hiding in plain sight and adding a sniping specialist who can come off screens and provide gravity to get others open would be a welcomed addition to the Boston offense.

BILL: I know we’re talking about future picks, but I’d love to get your opinions on what we might already have in the cupboard. Carsen Edwards still has two more guaranteed years on his rookie contract; do you see him making an impact next season? What about Tacko Fall and Tremont Waters? Do they get big league deals in 2020-2021?

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KEITH: I think Waters has a chance to be elevated to a standard contract, as sort of the Brad Wanamaker replacement. I still think the team will look for a veteran backup PG. Kemba Walker is probably going to miss games going forward, and Marcus Smart is always dealing with something. That’s a position you have to have depth at. I’m guessing Boston would love to get Tacko Fall back on another Two-Way contract to continue developing him. He came a long way this season, but he clearly needs more time. That’s got to be Boston’s hopeful outcome.

I’m less sure of what happens with Edwards. He showed so little both in the NBA and in the G-League. I had hopes he could maybe be a microwave type of scorer off the bench. I’m not ready to give up on him, but I’m also not counting on anything from him either.

ADAM: Young players continuing develop is a little bit of a catch-22. They need to get something resembling real minutes in order to improve against expected competition, but the Celtics as a win-now group can’t afford to give them those minutes until they prove worthy. With so many youngsters in need of those minutes (Edwards, Waters, Langford, Fall, Rob and Grant are in that category, too) it’s impossible to give everyone a fair shake at it.

Sprinkle in the uncertainty of a G-League season and we’re probably not going to get many answers on whether this cupboard is full, barren or anywhere in-between.

KEITH: I think there is a high likelihood we will see some of these guys moved in exchange for a minor asset, just to get off the salary. For example, someone like Edwards could into many traded player exceptions that are out there, or a team with cap space could take him on.

Maybe a bad team like the Knicks or Pistons could give him the minutes he needs to see what he is. And if it doesn’t work out, it’s not like they gave up anything to get him.

ADAM: Seems like there are a ton of options via trade, via free agency and through the draft to improve this roster. Ainge wasn’t so subtle in talking about their desires to add a piece or two that can help right away. We’re fortunate to be in a position from an asset standpoint to hopefully maneuver the offseason to bring in the best fits for the team.

The logistics might get tricky and the changes to the roster fairly minor, but this is a really good position to be in. Searching for complementary pieces is far easier than trying to find foundational cornerstones. It won’t be a quiet offseason by any means, and some new faces will freshen up the roster, but it likely won’t be a particularly loud winter, either.