Five Key Offseason Questions: Boston Celtics

Not every Celtic fan is in love with Danny Ainge‘s patient, meticulous approach to stockpiling assets and building the team’s roster, but that strategy began to pay major dividends in 2017. The Celtics made a strong second-half push to nab the No. 1 seed in the Eastern Conference, then took advantage of their pick swap with the Nets and some lottery luck to grab the No. 1 pick in the draft as well.

Of course, each of those accomplishments comes with a caveat. Despite their spot atop the Eastern Conference, the Celtics didn’t come anywhere close to knocking off the Cavaliers in the Conference Finals, and will need to add another impact player to their roster to help close that gap. As for the No. 1 overall pick, Boston became the first team in recent NBA history to trade that top selection in advance of the draft, sending it to Philadelphia for this year’s No. 3 pick and a future first-rounder.

Even after a 53-win season and a pair of playoff series victories, Ainge continues to turn current present-day assets into future pieces. Will that approach change at all this summer?

Here are five key questions facing the Celtics as the offseason begins:

1. What will the Celtics do with the third overall pick?"<strong

When the Celtics first completed their trade with the Sixers earlier in the week, there seemed to be two schools of thought for what Boston had in mind for its next move — the team would either select Kansas forward Josh Jackson, or use its newly-acquired picks in a trade for a star.

Several days later, it’s not clear that the Celtics will take either route. If the club keeps its pick, there’s no guarantee that Jackson will be the selection — many experts believe Boston may be leaning toward Jayson Tatum instead, and Jonathan Isaac has even been mentioned as a possibility. There have also been reports suggesting that the Celtics could trade down again, perhaps with an eye on a player like Dennis Smith Jr.

The Celtics are sitting in a great spot, and at this point there’s no real wrong answer for the club — whatever happens, Boston should come out of draft night with either a young potential star or a player who is already a star.

2. Is this the right time for the Celtics to cash in some trade chips?

Several teams are reportedly interested in moving into the top four in an effort to land Jackson, making the Celtics an ideal trade partner — there’s no guarantee Jackson would be available at No. 4, but with Markelle Fultz and Lonzo Ball considered strong favorites to be the first two picks, the No. 3 pick may be the spot for the former Jayhawk.

The Bulls and Knicks are said to have legit interest in Jackson, and each of those teams has been exploring trade scenarios involving its stars — Jimmy Butler in Chicago and Kristaps Porzingis in New York. Either player would be a terrific fit in Boston, though Porzingis, in particular, would be a perfect addition for the C’s. He’d be capable of providing the sort of rim protecting the club has been missing, without compromising short-term cap flexibility.

Still, if Ainge perceives the asking price for those players to be too high, he’s under no real pressure to make a move. Pundits and fans may be anxious for the Celtics to push the Cavs in 2017/18, but Ainge certainly recognizes that he has the team well-positioned for the next five or 10 years — not just the next two or three. There’s no urgency to go all-in within the next couple years, particularly with LeBron James not yet showing any signs of slowing down.

There are potential moves the Celtics could make that would improve the current roster without compromising the team’s ability to contend for the next decade, but striking a balance between those two goals will be the key.

3. What can the Celtics do in free agency?

Historically, the Celtics haven’t frequently landed impact players in free agency, but that changed last summer when the team poached Al Horford, one of the top veterans on the market, from Atlanta. A year later, Boston may try to repeat that feat, having been consistently linked to pending free agents like Gordon Hayward and Blake Griffin.

Creating enough cap room for a maximum salary offer to a player such as Hayward or Griffin will require at least one or two additional roster moves, but that shouldn’t be a significant roadblock if the Celtics are able to get a commitment from a star free agent.

Given Griffin’s injury history and the fact that he’s not an elite rim protector, Hayward looks to me like the better fit in Boston. However, if the Celtics end up landing a forward like Paul George or Jimmy Butler around the time of the draft, it’s possible they won’t pursue Hayward quite so aggressively. And even if they do go after Hayward and/or Griffin, the Celtics have no assurances — both players will be coveted by many potential suitors, and could earn more money by re-signing with their own respective 51-win teams.

4. Will 2016’s first-rounders arrive stateside for 2017/18?

When considering the Celtics’ collection of assets, their current players and future draft picks generally get most of the attention, but the team’s draft-and-stash prospects shouldn’t be overlooked. Guerschon Yabusele and Ante Zizic, last year’s 16th and 23rd overall picks, respectively, had very strong seasons overseas, and appear capable of being long-term pieces for the Celtics, assuming they’re not traded.

Both Yabusele and Zizic reportedly have interest in joining the C’s for the 2017/18 season, so Boston will have to decide whether the time is right to bring them over. Neither player will be expensive, but even their modest cap hits could compromise the Celtics’ ability to offer a maximum salary contract to a free agent, and if Boston doesn’t believe the youngsters are ready to contribute right away, it might make more sense to wait another year to start the clock on their four-year rookie contracts.

I still expect we’ll see at least one – and perhaps both – of those two draft-and-stash prospects arrive in Boston this year, but the decision is a complicated one and will require an agreement from both sides.

5. Which rotation players are keepers?

Outside of Isaiah Thomas, an MVP candidate in 2016/17, and perhaps Al Horford, the Celtics don’t have any All-Stars on their current roster. The team should be looking to increase its star power, either in the form of a current star or a young player with the potential to become one. But in order to have a shot at a great player or two, Boston may have to determine which of its “good” players are expendable.

For instance, Kelly Olynyk, a reliable piece of Boston’s frontcourt last season, is eligible for restricted free agency. If the Celtics intend to pursue an elite free agent, there’s a good chance they’ll have to renounce Olynyk’s $7.7MM+ cap hold to create the necessary room.

If the Celtics go the trade route to land a star, some combination of Avery Bradley, Jae Crowder, Jaylen Brown, Marcus Smart, and Terry Rozier would likely be headed in the other direction. Based on their current ability to contribute, their future potential, and their contract situations, which of those players will Boston view as most expendable?

I suspect that out of that group, the Celtics will prioritize keeping Brown. But if C’s get deep into trade talks with the Bulls, Pacers, Knicks, or another team, and the inclusion of Brown is a sticking point for that club, Ainge will have a tough decision to make.

Here’s where things currently stand for the Celtics financially:

Guaranteed Salary

Player Options

  • None

Team Options

  • None

Non-Guaranteed Salary

Restricted Free Agents

  • Kelly Olynyk ($4,187,598 qualifying offer / $7,735,033 cap hold)
  • Total: $7,735,033

Cap Holds

Projected Salary Cap: $99,000,000

Maximum Cap Room: $26,177,629

  • For our max cap room calculation, we assumed the C’s will keep their seven guaranteed contracts plus Jackson (whose non-guaranteed portion is cheaper than an empty roster slot), and accounted for cap holds for the No. 1 pick, Yabusele, Zizic, and an empty roster spot. That works out to $72,822,371, which doesn’t quite leave enough room for a max salary for someone like Gordon Hayward. However, Boston could create more cap space by stashing Yabusele and/or Zizic for another year, or by making a trade.

Footnotes:

  1. Jackson’s salary becomes fully guaranteed after July 15.
  2. Zeller’s salary becomes fully guaranteed after July 2.
  3. Mickey’s salary becomes fully guaranteed after either July 1 or July 15 (conflicting information available).

Salary information from Basketball Insiders and The Vertical was used in the creation of this post. Photo courtesy of USA Today Sports Images.

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