This offseason looks to be franchise-shaping level for the Boston Celtics as they have the distinct opportunity to add major talent to an already budding young roster. The average age of their roster this season was a mere 24.6 years old come playoff time — which was good enough for youngest of the 16 teams who qualified — so moving forward expectations will only increase exponentially for Brad Stevens’ group.

Here at Upside & Motor we like to have fun. We know our stuff, but fun is paramount in this industry and so we decided to reach out to Celtics guru Kevin O’Connor (@KevinOConnorNBA) for some help on this piece. Kevin writes for SB Nation, Draft Express, Sporting News and covers the Celtics for Celtics Blog of SB Nation.

Kevin will be the moderator of sorts for this group piece where four of our contributors at U&M pitched ideas for what Boston’s offseason should look like; in essence we unequivocally believe we can do what Danny Ainge does.

Reunited and it feels so goooooooood

Chris Reichert (@Chris_Reichert)

The plan going into the draft has to be adding more players to their already stellar, young core. Boston has 600 picks (okay they have eight) in the 2016 draft so clearly they cannot roster all those players for the 2016/17 season, however they should shelf the idea of consolidating picks for trades unless some once in a lifetime, the other side has David Kahn as their GM, type of trade offer.

The Celtics don’t have a single player over the age of 30 and they were the youngest team to make the playoffs with an average age of 24.6. League average this season is 26.8 and all the contenders are above that — Golden State 27.5, Oklahoma City 27.0, Cleveland 29.5 and San Antonio 31.6. While their young talent is budding and about to reach their respective primes, adding some veteran help will be vital to a win-now mentality they have to adopt.

If free agents around the league are smart and looking for a place to win for years to come this could be their future home. Brad Stevens is already talked about as one of the top young coaches in the entire Association, Isaiah Thomas got his chance to take the reigns and he ain’t givin em’ back, Bradley improved tremendously and Jae Crowder used his change of scenery to become on the massive contract bargains over the next four seasons (roughly $7M/year).

First I propose Boston let Amir Johnson and his non guaranteed $12M salary walk. He was solid for the C’s this past season, but that salary space will be needed for bolstering the front court via free agency post-draft. Along with him Jared Sullinger, Jonas Jerebko and John Holland will not be retained either. Those are merely for roster spots that will be needed for our younger talent with higher upside.

Right now the Celtics are slated to pick No. 3 overall via The Mighty Russians Brooklyn and the top two picks, in some order, will be Brandon Ingram and Ben Simmons in all likelihood. That leaves Boston to take 18-year-old Dragan Bender. Believe me when I say the front office will be thrilled to add a ridiculous talent like Bender to their already youthful roster. Bender can join a winning organization and, unlike most top-3 picks, learn as he goes and not be thrust into the starting lineup immediately.

The remaining first round picks are No. 16 and No. 23. My entire plan has room for two of their first round picks to be signed to the 2016/17 roster so they either have to combine these to move up, trade one of the picks for future pick/s, or select a draft-and-stash type of player for the future. At No. 16 they could feasibly select MSU grad Denzel Valentine and that would be ideal. He adds 3-point shooting, defense and comes from a team-first program so his assimilation to Boston would be painless.

I’m opting for Boston to retain the No. 23 overall pick and select Ante Zizic as a draft-and-stash guy. He’s a 19-year-old and at 6’11 plays with high energy in the Adriatic League right now. He’s been dominant this season and although he recently added a buyout to his contract for this summer, it’s still likely that he will continue to play with historic club Cibona Zagreb and develop even further while he waits for his opportunity to join the NBA. This is ideal for Boston because they add another big man for the future — imagine an eventual front court of Dragan Bender (18) and Ante Zizic (19)…annnnnd now I’m foaming at the mouth. Goodness.

Now, the Celtics have five second round picks (31, 35, 45, 51 and 58) and again no roster spots for any of them. Those picks are easier to move and while the purse might merely be future second round picks, it might make sense to go that route. As a huge fan of the NBA D-League however I suggest the Celtics use at least three of these picks and use the domestic draft-and-stash option with the Maine Red Claws. There is no limit to how many draft rights players you can send to your affiliate and this will keep those second rounders close, while they get to work with Boston’s personnel and with the eventual schemes they hope to use when they get their shot in the NBA. This also allows Boston to keep an eye on these guys in case there’s a potential Norman Powell or Josh Richardson in their midst — those were the only two second round guys who made a real impact this season so the likelihood isn’t great, but it’s there.

Now comes free agency and this is where the tide can turn for the club. Adding young talent is paramount, however Boston needs to add winning pieces to their front court, as with the cuts suggested earlier they only have Kelly Olynyk, Jordan Mickey and Tyler Zeller left.

First — make a HARD pitch to Al Horford. Yeah, he’s had a great home in Atlanta for his first nine seasons but he’s ripe for the picking and Boston should move swiftly to add this talented power forward to their mix of young wings. Horford makes all the right plays and while his 15/7 don’t jump off the page, he does all the little things that help his club be successful. This season he even added a 3-point shot hitting 88 (34.4%) after only amassing 21 total his first eight seasons. Horford is still just 29-years-old as well.

Second — call Joakim Noah’s agent and profess your undying love for the exquisite center. He’s had a rough go of it the last two seasons but he’s unrestricted and man oh man would he look great playing next to Horford. Noah is 31-years-old and would bring endless experience along with his childlike, college-level energy that was so contagious when things were going well for him and the Bulls. The Bulls had a sketchy season and now find themselves out of the playoffs and in the NBA lottery, so pitching a change of scenery with a young, talented roster could easily sway Noah to jump ship.

I can’t remember exactly but I think the last time these two played together but I’m positive it turned out alright. Maybe ask current Thunder coach, Billy Donovan about that.

After all these moves, here’s the depth chart for the 2016/17 season:

PG: Isaiah Thomas – Marcus Smart – Terry Rozier

SG: Avery Bradley – Denzel Valentine – James Young

SF: Jae Crowder – Evan Turner – R.J. Hunter

PF: Al Horford – Kelly Olynyk – Jordan Mickey

C: Joakim Noah – Tyler Zeller – Dragan Bender

Boston immediately jumps to the top of the East with the likes of Toronto and the real contender of the bunch — the Cleveland Cavaliers and all becomes right with the world; you’re welcome.

Kevin’s Response:

You’re right that the Celtics, contrary to popular belief, don’t need to rush into a move, but I don’t think they should “shelf the idea of consolidating picks.” It should be a priority to consolidate, even if it doesn’t bring back a superstar in a trade. They have the advantage of being able to bring nearly every player in for a workout, so if there’s a player they have their sights set on, then they should be aggressive in targeting him. They’ve done it in the past, so I expect it to be a actionable plan again this year.

However, if the Celtics do stay in their draft slots, Bender, Valentine, and Zizic are three strong selections. Valentine in particular is a significant value pick at No. 16. I have Valentine ranked as a Tier 2 prospect in my 2016 NBA Draft Guide.

Your second round plan is where things can fuzzy, because a player would need to agree to a domestic draft-and-stash option. I’m not optimistic any high-major school player will be enthusiastic about that, so picks should be consolidated when possible. It’s more likely to happen with a mid-major (like it did in 2015 with the Celtics draft-and-stashed William & Mary’s Marcus Thornton).

The free agency plan is just okay to me. None of the signings help their spacing; they rank 29th in 3-point percentage over the last three seasons and Al Horford is only average from three. Bringing in Horford and Joakim Noah would also stunt the development of all the youth on the roster. I like the idea of Noah, but I don’t like him in this scenario.

This is a solid overall plan and the Celtics would possibly be “better” in the wins column, but it doesn’t move the needle towards championship contender status. If the Celtics aren’t able to land a youthful piece – or a superstar – then taking a step back in veteran talent next year is a better option so they can focus more on development. In the depth chart provided, there’s absolutely no wiggle room to play small ball, and there are very few or no available minutes for the youth.

The Frontcourt Shake-Up

Brendon Kleen (@BrendonKleen14)

As crazy as it might have sounded before the playoffs, re-signing Evan Turner seems like it should be at least a long consideration on the part of Ainge and the rest of the front office. The other guys (Zeller, Sullinger, and Jerebko) are entirely replaceable. He earned a raise, but shouldn’t command any more than $4 or 5 million over a few years. That’s doable.

They need help down low; as exciting as it may be to imagine them landing a marquee free agent big like Hassan Whiteside, that’s probably not happening. That being said, the Horford rumors aren’t ending any time soon either. He doesn’t quite fit their championship time table, but is so talented that you would never argue with him donning the beantown green.

Alas, someone like Bismack Biyombo, Ian Mahinmi or Festus Ezeli would be exactly what they’re looking for to fill the void next to Kelly Olynyk or in small lineups with Crowder or another wing (or Marcus Smart) at the four. They should probably take a look at replacing Jerebko as well- someone like Luol Deng or Marvin Williams to bang around defensively, make shots and play the intelligent Brad Stevens brand of basketball.

If they feel confident in their abilities to go and get and free agent or two and like what they see in this year’s class, the draft is pretty much wide open for them. Chris Stone’s last mock draft for FanSided had the Celts taking Utah’s Jakob Poeltl with the Nets’ pick, MSU’s do-it-all Denzel Valentine with their own, and foreign stretcher Juan Hernangomez with the Mavericks’ pick. I like the idea of Valentine playing under Stevens- he’s a similar type of player as Gordon Hayward and Matt Howard- but so is Turner.

I actually prefer that they flip the high pick- I was impressed by Terry Rozier after Avery Bradley’s injury in the playoffs, and James Young has yet to really develop. Give those guys time and take a guy in the first to replace the outgoing free agents. I like someone like Taurean Prince or Wade Baldwin to solidify the backcourt ahead of the other moves I have brewing and a late-first prospect like Ivica Zubac to replace the outflux of bigs coming later.

Now, I’d like to make some deals, and I’m feeling a little Love Drunk. His style is a match made in heaven for Stevens’ offensive style, and despite Cleveland’s magical coalescence, no one’s forgotten the discomfort that clouded the first two years of Love’s tenure there. I’ll preface this dice-rolling by saying that, in all honesty, it’s a long shot that David Griffin and the rest of the decision-makers in Cleveland value draft picks and long-term stock enough to prefer a Boston deal over those of other suitors.

But screw it. I think something like this (with Boston also giving up the Nets’ pick to Cleveland and the juicy Sixers second-rounder to Portland for their trouble) makes a lot of sense for both sides:

They’ve got to use those assets at some point, and with the rest of the roster developing nicely, it feels nice to cash in on what they’ve made Crowder into and the depth they’ve amassed across the board. Few teams could afford losing three rotation players, but I really think Boston can.

Lastly, I don’t expect them to use all four of their remaining second-rounders, but there are prospects in the latter part of the draft that I like for them (AJ Hammons, Brice Johnson, or Zhou Qi to name a few).

That being said, these moves would leave the rotation looking something like this:

PG- IT, Smart, Rozier

SG- Bradley, Smart, Rozier

SF- Turner, Deng, Young, Prince

PF- Love, Deng, Hammons

C- Ian Mahinmi, Zubac (probably getting stashed), Hammons

It’s probably not enough cash-in on the draft capital, and its a lot of valuable player movement, but this has to be the summer when the Celtics reap value from their abundant resources.

Kevin’s Response:

I hate this plan more than Vegeta hated Goku in the early seasons of Dragon Ball Z. I still like Kevin Love, but not for that haul. Jae Crowder’s defensive versatility is tremendously valuable in today’s positionless league, so adding the Brooklyn pick and Olynyk and the early second on top of Crowder is far too much. Love is still a great player stuck in the wrong situation, but I don’t value him like I did two years ago. The league has changed so much and I think Love’s defense could become even more exploitable as more teams get smaller, faster, and more versatile.

Evan Turner will command a lot more than $4 or $5 million. Probably more like $14 or $15 million — $10 million, at the least. I praised the Celtics for signing Turner in 2014 (see here and here), but now I feel like I’m the only one saying they likely shouldn’t re-sign him. For all the good Turner brings, his presence stunts the development of Marcus Smart, who I believe is on the verge of a breakout season, and if Turner plays off-ball he hurts the team’s spacing. Unless Turner takes a discount to stay in Boston, bringing him back likely isn’t in the best long-term interest of the franchise.

As Danny Ainge said at a recent press conference, the Celtics have “plenty of urgency to try to do our Plan A and our Plan B and our Plan C, but you really have to be careful if those don’t come about in what you do with those assets.”

With this plan, it simply feels like the Celtics weren’t careful about what they did with their assets. As you yourself said, “it’s probably not enough cash-in on the draft capital.”

The 3-5 Year Plan

Chris Stone (@cstonehoops)

Plan A for the Celtics should involve a free agency pitch to Kevin Durant centered around playing in the softer Eastern Conference while surrounded with a promising young core and the potential to package assets for another big name like DeMarcus Cousins or Blake Griffin. However, it seems unlikely that Durant will leave Oklahoma City and if he does, it likely won’t be for a Boston team that lost in the first round of the playoffs when Golden State and San Antonio are potential suitors.

Without Durant, how quickly can the Celtics actually compete for an Eastern Conference title given that the Cleveland Cavaliers are set up to run rampant over the East for the next couple of seasons? The solution is to accept that Boston’s window is unlikely to occur in the next few years and instead to invest in a plan aimed at winning the East in the next 3-5 seasons. That means cultivating a young core using the draft and development in the D-League to build out a roster of homegrown talents before attempting to make a big splash in free agency in the future.

The good news for the Celtics is that with plenty of Brooklyn’s first round picks in their pocket, they don’t have to engage in a Sam Hinkie-style tank to rebuild a championship contender.

This “Process”-lite rebuild begins with the 2016 NBA Draft. Boston has eight (!!!) picks and thus plenty of opportunities to find a gem. How the ping pong balls fall on May 17 will help determine the direction of the Celtics’ roster. If Boston improves their draft position (currently third thanks to Brooklyn), they could end up with LSU’s Ben Simmons and build out their roster around the ball-handling power forward or they could select Duke’s Brandon Ingram, a prototypical two-way wing with piles of upside and the ability to plug-and-play in various systems. For our purpose, though, let’s assume the Celtics stay put at number three.

The choice here is Maccabi Tel Aviv’s Dragan Bender, an 18-year old power forward with a jump shot and the agility to guard multiple positions on switches defensively. Bender isn’t NBA-ready yet, but with a couple of years of seasoning, he could become the type of versatile big man that is so prized in the Association today.

Boston has two remaining first round picks. At 16, the Celtics will have plenty of options, but if Michigan State’s Denzel Valentine is available, he makes sense. Valentine is a 22-year old guard who has experience shooting off of screens, working with the ball in his hands, and is an excellent passer. With the 23rd pick, Boston can once again works to fill out a frontcourt that will have plenty of open space. I currently have the Celtics selecting Juan Hernangomez here, a 6-9 power forward who, like Bender, can help space the floor on offense. With five second round picks, the Celtics can swing for the fences by selecting high upside prospects who can grow with the Maine Red Claws, Boston’s D-League affiliates.

In free agency, Boston can retool its front court for the short-term where the aim is to simply make the playoffs, not challenge for the Eastern Conference title. To start, we can shed the contract of Amir Johnson and allow free agents Tyler Zeller and Jared Sullinger to walk. Boston’s first target should be Toronto’s Bismack Biyombo who has a player option he likely won’t exercise this offseason. Biyombo will provide the Celtics with the rim protector they currently lack and a high-energy rebounder on the boards. He is also only 23-years old, which is in line with our plan to compete in 3-5 years. 29-year old Marvin Williams is the second target. Williams experienced a resurgence playing power forward for Charlotte this season and his outside shooting will greatly help a Boston team that ranked near the bottom of the league in three-point shooting in 2015-16. While Williams may not be part of the long-term plans, he is a great short-term option to help keep Boston in the playoffs.

The Celtics still need a small forward to come off the bench in this scenario. Resigning Evan Turner to a short-term deal may make the most sense. Turner can likely be had on a relatively cheap contract and is a guy who can help groom some of the younger players on the roster.

That sets up the following 2016/17 rotation:

PG: Isaiah Thomas – Marcus Smart – Terry Rozier

SG: Avery Bradley – James Young – RJ Hunter – Denzel Valentine

SF: Jae Crowder – Evan Turner

PF: Marvin Williams – Dragan Bender – Juan Hernangomez

C: Bismack Biyombo – Kelly Olynyk

There’s one more spot open on the roster, which will likely be given to one of the Celtics second round picks. This rebuild isn’t the sexiest. Boston won’t compete in the East for at least a couple of seasons, but bringing back a similar roster while attempting to retool the front court is a nice way to at least continue to make the playoffs while grooming talented players for the future.

Boston has the right to swap picks with Brooklyn in 2017 and it looks like that selection could be another top five pick. If the Celtics could land Josh Jackson, Harry Giles, or Jayson Tatum to go alongside Bender, the future will look bright in Beantown.

Kevin’s Response:

You’re right about Plan A. In addition to the pitch you mentioned, they should also focus on the history of the Celtics. Durant’s number could someday hang in the rafters. I believe he cares a lot about basketball history. So with that in mind, I wouldn’t underrate the Durant scenario. It’s most likely he stays with the Thunder, but I don’t think it’s any less likely that he signs with the Celtics compared to the Spurs or Warriors.

However, assuming they don’t get Durant, this plan most closely resembles the approach I’d take this summer. This is a winning, forward-thinking draft plan.

Bender, Valentine, and Hernangomez are three of my favorite prospects this year in their respective draft ranges. Bismack Biyombo, who was also mentioned in Pitch #2, is the big man I’d target in free agency regardless of the plan. He’s young, at 23. He fills two needs: defensive rebounding (Celtics were 26th in DREB%) and rim protection. And he likely comes on a value contract.

I’m not sure signing Marvin Williams is necessary under this plan, but I’m not against it if the price is right and it’s a short-term contract. In this proposed scenario I also think Evan Turner would continue to block the youth at the guard/wing positions, like I do in Pitch #2. But overall it’s a strong plan that blends youth and flexibility, as well as a competitive team that is positioned to acquire any star that becomes available through trades during the year or free agency in 2017.

Get ALL of the Athletes!

Trevor Magnotti (@IllegalScreens)

Boston’s roster has a few good athletes, but they are lacking athletes in a few key positions. To keep with the Celtics’ theme of building a well-balanced roster with plenty of options to choose from, I have four major needs that I need to address for the Celtics:

Athletic Rim Protector A secondary ball-handler Shooting Rebounding, particularly on the defensive end

With plenty of picks, young players, and cap space, there’s plenty of ways to address these.

First, let’s address the current roster. Amir Johnson and Jonas Jerebko’s team options are getting picked up, for now. I’m bringing back Tyler Zeller on a cheap deal, but letting Jared Sullinger move on from his qualifying offer. Sullinger had a decent year last year, but he has an injury history and we can find an upgrade. Finally, Evan Turner gets to move on which leaves me three roster spots to fill.

Now, we turn our attention to the draft. Eight picks is a lot, and I’m really only hoping to come away with one or two guys who are guaranteed to join the roster next year. The first is the top-six pick, which we will assume will be the third pick for this purpose. At three, I’m grabbing Dragan Bender, who eventually I will hope can check the shooting and rim protecting boxes for me. Bender and Olynyk would be a nice combo on both ends, as they would give Boston two frontcourt shooters and a mobile shot blocking prospect to pair with Olynyk’s underrated defensive hustle.

With the 16th and 23rd picks, my plan is to try to do what the Jazz did in 2013 and the Nuggets did in 2014: Package those picks and one of their five 2nd rounders to move back up into the lottery. The Celtics never seem to have much interest in international prospects, and if they can grab one of the project power forwards like Marquese Chriss or Skal Labissiere, or Timothe Luwawu, by trading up with the Magic or Bucks, that could be a better idea than them gambling on guys like Furkan Korkmaz or Ivica Zubac. If they can’t make that deal, Korkmaz is a good option at 16, and I’d target Malik Beasley or Taurean Prince with pick 23, in the name of picking up shooting and playmaking.

In the second round, the Celtics could stand to pick up a couple of stash guys and high-upside D-League prospects. But they aren’t going to be picking up five guys in the second round. I’m already hopefully dealing one in the trade-up deal, and with the other ones I’m looking to deal away picks to teams like the Nets, Cavs, or Lakers, who might be interested in buying a 2nd rounder. If I can pick with two, trade one, and sell the final two, that’s a reasonable way to handle those picks.

Trades are fun to picture for the Celtics, as they’re always in the market to wheel and deal. They’ll be making moves for Dwight Howard, Al Horford, and DeMarcus Cousins this summer if they’re available, but I’m going to aim a little lower on the totem pole. I’ve already at this point gotten a couple of athletic bigs and probably one shooter (like Jake Layman) from the draft, but I need to address the frontcourt a little more, and there’s a power rebounder who would be an upgrade over Amir Johnson that I’d be interested in:

Faried’s energy and rebounding ability would make him a nice fit here, and dealing Young (And/or Terry Rozier) would open up a roster spot. Denver gets a veteran presence in their frontcourt and another young piece to develop, and potentially a 2nd or two, so it’s not an awful return for them. With Faried around, the Celtics will have three great forwards to build around up front, and trading Young opens a roster spot.

Finally, I use the remaining cap space to get a secondary ball-handler and another cheap shooter. On the wing, a former Celtic is one of my top targets, as Courtney Lee could be a nice fill-in as a shooter and secondary creator. Then, because I’m shameless, I’m going to sign Mirza Teletovic as another shooter. He’s a shooter with excellent touch and rebounding muscle, and he’s a great veteran presence. Every NBA team should sign Mirza Teletovic, and Boston is an NBA team, so they should go after him.

So, in summary, here’s my ideal 15-man roster for 2016-2017:

Starters: Isaiah Thomas, Courtney Lee, Jae Crowder, Kenneth Faried, Kelly Olynyk

Bench: Marcus Smart, Avery Bradley, Dragan Bender, Jonas Jerebko, Mirza Teletovic, Jordan Mickey, Tyler Zeller

Deep Reserves: Terry Rozier, Skal Labissiere, R.J. Hunter

D-League: Jake Layman

International Player X

I’ve created more shooting, I have a bunch of excellent, athletic wing options, I have rim protection growing and developing with Bender, Mickey, and Skal, and I didn’t overpay for Dwight Howard or totally raid the future pick arsenal. I instead filled needs, maintained flexibility, and progressed towards turning into a Hawks-style two-way squad.

Kevin’s Response:

This is a solid, conservative approach. Your four major needs I agree with, though I think there’s much less need for a secondary ball-handler. Marcus Smart is ready to take on that role and Terry Rozier could take a step next season.

I have never been much of a fan of Faried, so this is a personal preference more than anything. I prefer the Biyombo free agent route, or simply going with the youth movement, though in your proposed trade it’s very fair on paper. I don’t think Courtney Lee is necessary because he blocks the development of R.J. Hunter, Terry Rozier, and Marcus Smart. Signing Mirza Teletovic does the same thing to the frontcourt. There would be no minutes for Dragan Bender, Jordan Mickey, or Skal Labissiere.

Overall though, this plan still maintains flexibility, which should be the priority if the Celtics are unable to make a splash, which is why I don’t mind it compared to Pitch #1, which I believe locks the team into a plan and hinders their flexibility, or Pitch #2, which I think depletes them of their assets.

Other Thoughts from Kevin about the pitches:

I’m stunned Jimmy Butler’s name wasn’t brought up by anyone as a trade target. It seems reasonable for the Celtics to pursue him. No mention of Nicolas Batum as an option is also a surprise, though he’ll likely be back in Charlotte. He’s a solid Tier 2 option if they swing and miss on Durant.

Evan Fournier and Allen Crabbe are both restricted free agents, but would be upside additions. Crabbe seems on the verge of a breakout season after coming along so much in Portland. And Fournier would give Brad Stevens a sharpshooter.

Ainge said this at a recent presser, which sums up my thoughts on this Celtics offseason: “I have no sense of [how different the Celtics will look next year]. I have hope, but I have no sense. There are scenarios where our team could be better and significantly better, and there are scenarios where we have younger players that are maybe not as good from a win record standpoint, but with development standpoint being a much, much higher ceiling.”

There are three D’s: drafting, dealing, and developing. The Celtics need to focus on all three, and so doesn’t every single team. But one of their issues this season was the lack of ball handling opportunities for Marcus Smart, and the lack of playing time for Terry Rozier and R.J. Hunter. Some of these plans put a little too much emphasis on adding free agents, instead of feeding playing time to the rookies, who are ultimately the players that can be fostered into more valuable assets or core pieces.