Five crucial choices the Celtics will face in 2019

The new year will certainly be an interesting one for the Celtics. A season of great promise gave way to an inconsistent and, on several occasions, puzzling first half for Brad Stevens' crew. What will 2019 have in store for the green — both for the rest of this campaign and a crucial offseason? Here are five questions that will go a long way to answering that question:

1. How all-in is Danny Ainge on this season? This is a tougher decision for the front office than it appears at first glance. On the one hand, the Celtics remain stuck as the fifth seed in the Eastern Conference 35 games into the regular season amid a schedule that includes home losses to the Magic, Suns and Knicks. On the other hand, there may not be another season in which this group has this type of depth at their disposal up and down the roster. It has not translated in the win-loss column so far, but Kyrie Irving is playing like an MVP candidate and Marcus Morris is having a career year — two things that are not guaranteed to continue beyond 2019. With the very real possibility that half of this team’s rotation could be wearing another uniform next year (via trades or free agency losses), the Celtics still are in a pretty unique position to make a run at the title with the Warriors looking more vulnerable than they in years.

So what would constitute the Celtics going all-in on this season? A couple of options loom as possibilities. The first will be a potential move at the trade deadline. Danny Ainge has refused to move first round picks for a potential rental in recent years as he has focused on stockpiling assets for bigger moves. Now? The Celtics contending window may be deserving of a boost, particularly if some of the bench pieces (Terry Rozier, Daniel Theis, Jaylen Brown) aren’t meshing with the team’s success on the floor on a regular basis. I wouldn’t expect those guys to be dealt, but trading a late first round pick and a player with no trade value/roster filler (Brad Wanamaker/Jabari Bird) for a shooting upgrade with the second unit would raise Boston’s ceiling by a bit.

The other thing to watch for is just how aggressive Ainge will be on the buyout market. The Celtics are in the luxury tax but also have the full mid-level exception (nearly $6 million at their disposal) that they can offer to any one player. While convincing a prospective free agent that Boston has a big enough role for them might be a challenge, a big money offer will help on that front. With the buyout market expected to be active (with so many tanking teams in the East), the C’s level of pursuit will say a lot about.

2. Is Jayson Tatum going to be on the table for Anthony Davis without any guarantee about re-signing? With every Kings win and missed 3-pointer by Jaylen Brown, the reality is becoming more and more apparent that the Celtics are going to need to include Jayson Tatum in an offer for Anthony Davis this summer to outbid what will be a long list of potential bidders. Tatum serves as a bit of trump card as far as a prospect with All-Star capabilities who is on a bargain rookie deal for the next two seasons. The Pelicans will surely get offered All-Stars for Davis (who are making max money) as well as a long list of intriguing young players, but no one will have the mix of potential and low cost that Tatum provides that should be appealing to a New Orleans team that will be on path to rebuilding if Davis is gone.

There is no question Tatum will be on the table if Davis signals he would re-sign in Boston, but that’s far from a sure thing to happen this summer given his representation (Klutch Sports) and relationship with LeBron James in Los Angeles. The Celtics’ can top the Lakers’ best offer if Tatum is included in any deal, but will they if he has reservations about re-signing in Boston? It’s a question that will hang over the Celtics summer if Boston falls short of the NBA Finals. Will Ainge bet that the team’s culture and chemistry would entice Davis to stay? Or would the prospect of Davis walking away keep Tatum out of any final offer for the All-Star? The answer to that decision won’t be known until we see what this group is capable of doing this postseason.

3. What happens to Gordon Hayward if he looks more like a role player than an All-Star for all of 2019? Looking for the two-time All-Star to resemble his old self in the first two months was always going to be a tall ask. We’ve seen signs of the old Hayward so far (plus rebounder, good distributor) but it’s evident that he doesn’t feel comfortable yet within his old body. That’s not a surprise to those in the Celtics organization, who always anticipated that we would see the better side of Hayward in the second half of the 2018-19 regular season.

The bigger question that no one wants to tackle right now behind the scenes is what exactly happens with Hayward if he is producing at largely the same level at the end of 2019 as he is right now. No one hopes that is the case but the possibility remains Hayward will just never get back to the All-Star level he was before suffering the horrific ankle injury last season. Hayward will be given the opportunities to bounce back for the rest of next year and there’s virtually no chance he’s dealt this summer based on the message it would send around the league (signing a max free agent and dealing them less than two years later is not a good look). However, Ainge is a realist and he knows that this group will be at a crucial part of their title window over the next two seasons while facing a sizable luxury tax bill. Given the strong connection between Hayward and Stevens, even some consideration of a move involving Hayward would send shock waves throughout the organization. However, if the 28-year-old is still averaging 12 points per game a year from now while making $30 million per season, it’s going to be a challenging situation for Ainge to navigate.

4. Do the Celtics believe Al Horford will stay healthy enough for another big investment? Al Horford has already made clear to BostonSportsJournal.com he would love to spend the rest of his career in a Celtics uniform. However, at age 32, the signs of regression have already risen to the surface in the midst of Boston’s rough start to the year. Horford is rebounding and shooting free throws at a career-low rate in the midst of dealing with a knee issue that has hampered him over the initial two months of the year.

Horford’s 3-point shooting (35 percent) has started to return and he remains a crucial part of this team’s future, especially if Davis does not end up landing in Boston in one of the next two seasons. Still, Horford has played over 27,000 minutes in the regular season and postseason and it’s hard to find big men that don’t tail off significantly as they head into their mid-30s. Horford has a player option for next season at $30 million and the Celtics could benefit significantly by getting him to lower that number in exchange for adding on a couple more years of security. Will that type of exchange backfire though if Horford’s production keeps falling off or he can’t stay on the floor? Will they better off letting him play out his deal and getting him under contract at a lower number in 2020? In the midst of Irving’s prime, this is a decision that the Celtics must be right on, whatever path they choose.

5. Will the Celtics find a way to make room for Marcus Morris for 2019-20? The easy answer to this question at the start of the 2018-19 season was no. However, as the veteran forward flirts with the 50/40/90 club in the midst of a career year, his value has risen exponentially over the past couple of months. The Celtics own his Bird Rights, so the team has the ability to pay him whatever they see fit when he hits the open market this summer. They also won’t have the ability to replace his production with a price that goes beyond the mid-level exception ($6 million) with another free agent since they will be over the salary cap.

The common thinking before the year began was that the far-cheaper Semi Ojeleye would eventually step into Morris’ role after he departs for a bigger payday. However, after Morris played his way into the starting five and put together the second best season to date on the Celtics roster (behind Irving), it’s evident that losing the stretch forward would be a huge hit to the team’s offensive firepower. The dropoff in 3-point shooting from guys like Jaylen Brown and Hayward has made the need for a shotmaker like Morris to spread the floor around Irving more crucial than ever. Letting him walk for nothing this offseason will be a step back for the franchise in the midst of their contending window. It’s a situation that could be similar to the James Posey situation in 2008, an aging veteran who earned a huge deal in Boston. The C’s made the right decision to not match his four-year deal (Posey was out of the league by the end of it) but his absence over the 2009 and 2010 seasons loomed very large as the C’s fell short of a title. If Morris proves to be just an integral to a deep playoff run this spring, it will hard to justify letting him walk into the sunset.