5 Reasons Gordon Hayward, Kemba Walker Will Dictate Celtics Offseason

Getty Gordon Hayward, at left, and Kemba Walker, of the Celtics

When the 2019-2020 season eventually comes to an end this fall, there will be two important dates that team executives will be keeping a close eye on: October 16’s NBA Draft night and October 23 – the first day of free agency.

But if you’re the Celtics there’s a third date: October 17.

That’s the last day for Gordon Hayward to decide whether he will be opting-in to the final year of his four-year contract – worth $34 million – or testing the free agency waters. Hayward’s decision sits at the top of Celtics president of basketball operations Danny Ainge’s biggest concerns list and is also a story that tops off my Top 5 Celtics offseason storylines.

Gordon Hayward’s expiring contract

It’s sometimes hard to believe it’s been three years since  Hayward was officially introduced as a member of the Boston Celtics. A lot has transpired since that press conference at TD Garden in 2017. Not even Kyrie Irving’s famous “it’s about to be crazy, G” could prepare Hayward for the most tumultuous span of his career.

But if there’s one positive takeaway from Hayward’s time in Boston, thus far, let it be remembered that the veteran guard did the best he could with the hand that was dealt, and throughout the 2019-20 regular season he shined. In the shadows of Kemba Walker’s first All-Star season in Boston, Jayson Tatum’s ascension to stardom and Jaylen Brown’s first 20-point scoring season was Hayward, who consistently stuffed the stat sheet in nearly every statistical category while shooting at a career-high clip.

Hayward’s 17.3 points, 6.5 rebounds, and 4.1 assists while shooting 50.2% from the floor isn’t easy production to come by across the league, and it’s especially difficult to command those kinds of numbers from your team’s fourth scoring option. Hayward has been that good. It’s been somewhat overlooked, unlike Hayward’s $34 million price tag — a player option that one source told Heavy.com they believe may be “too much money to pass up.”

Speculation surrounding Hayward’s decision will certainly be the most talked-about Celtics story of the offseason. Expect Danny Ainge to uphold his due diligence in trying to restructure Hayward’s one-year, $34 million contract into a new team-friendly short-term deal to keep Hayward around for another two-to-three years but if both sides are unable to come to an agreement, it’s still in Hayward’s best interest to opt-in with the Celtics.

For starters, Hayward would maximize his dollars for the 2020-21 season and it would also give Hayward another contract year to prove to other potential suitors that his numbers of this season are not a fluke and that he can still perform at not only a high level but do it for a contending team. Staying in Boston for another year keeps him competing against elite talent — something Hayward would not be able to say if he were to leave Boston this offseason for a non-contending lottery team, which is what the buyer’s market will be filled with come October for teams like the Pistons, Hornets and (of course) the Knicks to make their pitch towards top-tier free agents.

If he comes close to matching his scoring numbers of 2020, expect Hayward to cash in another long-term contract in 2021, most likely, outside of Boston. One team that comes to mind is the Miami Heat — a team that was interested in signing Hayward back in 2017 and is reportedly expected to be big buyers in 2021’s free agency market.

Kemba Walker’s Health

By the end of the 2019-2020 campaign in Orlando, the Celtics should have a better understanding of what they are dealing with in regards to Kemba Walker’s left knee. Seeing how Walker’s body responds to a grueling eight-game schedule followed by a congested postseason run should indicate whether or not Walker – worst-case scenario – will require any type of surgery after the playoffs.

The 30-year-old All-Star has never dealt with a significant injury throughout his nine-year career. The restart in Orlando was admittedly “frustrating” for Walker, who continues to miss practice time with his teammates. At Walker’s age, things could go from bad to worse rather quickly when it comes to naggy knee injuries, especially for an undersized guard like Walker;who heavily relies on his speed and agility on the offensive end.

Boston’s approach with Walker – the team’s $140 million investment – has been overly precautious of late and for good reason. Walker’s leadership is crucial for the Celtics’ championship aspirations and with the playoffs still weeks away, don’t expect to see Walker clocking in over 30 minutes in all eight of the Celtics’ seeding games.

However, Walker will eventually hit the floor without any restrictions and that’s when we’ll know if he’s truly capable of returning to his old self.

Celtics’ Free Agency Options

With the Hayward option looming and half of the roster under contract, the Celtics will most likely not be making any big free agency signings come October. If Hayward ultimately decides to opt-in, Boston’s core of Hayward, Kemba Walker, Jayson Tatum, Jaylen Brown, and Marcus Smart should be enough to keep the Celtics in contention to win the East in 2021. However, it doesn’t leave Ainge with much to offer at the free agency pool.

Still, Boston is a team well-suited for building from within. The development of Grant Williams, Romeo Langford, and Robert Williams will say a lot about Brad Stevens’ second unit in the near future, and all three are seemingly trending in the right direction. “I think the most encouraging thing has been the play of our second unit, per se, would be what I’m really excited about,” Stevens said last month after practice. “I think guys have the right stride to be very impactful.”

Stevens has the right pieces to mold his second unit into a deeper group. Enes Kanter, who currently leads the team in rebounding (7.7), has a player option for next year and is someone the Celtics will need to make sure they retain for the final season of his two-year deal – Stevens’ bench is going to certainly need it.

Does Boston Need to Trade for a Big?

If the narrative surrounding the Celtics’ lack of size hurting Boston in the long-run hasn’t changed by October, my guess is one of two things didn’t happen throughout their postseason run:

Either, No. 1, the Celtics reached the NBA Finals with Daniel Theis leading the frontcourt or No. 2, Brad Stevens ran small-ball at the end of games with Marcus Smart at center to help them win the East. If neither happens and the Celtics bow out of the playoffs before the Finals, I still don’t like the idea of Stevens giving up on Theis, Kanter, and Robert Williams – at least, not yet.

All three bigs spent a great deal of time battling injuries throughout the 2019-20 season. But now that Stevens has been granted an opportunity to have all three at somewhat full strength from now through the start of next season, he’s going to seize that chance rather than bring in outside help.

Tremont Waters’ Development

The 2019-20 season was good for Tremont Waters. It didn’t take long for him to heat up the G-League as the leader of the Maine Red Claws, he pretty much got going from the get-go.

After getting the nod in Stevens’ starting lineup, Waters went on to win G-League Player of the Month honors for November and then went on to average 18 points, 7.3 assists, 3.2 rebounds and 1.9 steals in 36 games for Maine. He also finished sixth in assists, 14th in steals, and finished third for the G-League MVP award. He won the G-League’s Rookie of the Year award.

But will any of this translate at the NBA level? The jury is still out. Waters could go anywhere from playing another season in Maine, earning a final roster spot in 2021 or playing meaningful minutes in Stevens’ backcourt. Walker’s health does come into play here, if the veteran point guard needs time off at the start of the 2020-21 season, Waters will certainly be spending plenty of time in Boston.

Either way, it’s a storyline you’re going to want to keep tabs on. Seeing Waters earn meaningful minutes in Boston could be on the horizon sooner than anyone expected.