Boston Celtics: 3 big questions heading into 2019-20

1. Who will be part of the future?

Jaylen Brown becomes a restricted free agent at the end of the upcoming season and Gordon Hayward has a player option worth $34.1 million. Followed by Jayson Tatum hitting the restricted free agency market the following year, the Celtics have some decisions to make.

Having three players who occupy similar positions on the floor proved difficult last year, with both Gordon and Jaylen finding themselves as part of the second unit. Each brings something different to the team in terms of skill set and each player deserves a role on this team or any other NBA team.

Assuming the rumors surrounding Danny Ainge’s refusal to include Jayson Tatum in the Anthony Davis trade talks are true, it would be safe to assume Tatum will either get extended or re-signed when the time comes.

This leaves just Brown and Hayward with questions hanging over both of them Ironically both of these players are entering a pivotal year. Brown has watched draft classmates Ben Simmons and Jamal Murray get massive contracts in recent weeks. With a weak free-agent class next year and multiple teams able to clear up max cap space, Brown will receive a large offer sheet somewhere.

Hayward’s story is far more unclear, able to opt into another year on his contract should he choose to. Following a disappointing season last year as he tried to recover from the broken ankle sustained during the opening game of the 2017-18 season, all eyes will be on Hayward to show signs of the player he was pre-injury. Should he be unable to reproduce that type of play this year it will be difficult to see how he fits in with the team long term.

Hayward is an enigma though. If he starts this season much improved then he could be playing himself into becoming a trade asset. Start the season poorly and the Celtics could look to cut their losses. However, much depends on how they intend to move forward. Do they see Hayward or Brown as the player to compliment Tatum, Kemba and whoever else they bring into the fold?

Brown could be an intriguing trade chip for a team looking to blow it up and enter rebuild mode. Young, athletic and with deep playoff run experience, the sky is the limit if he can improve his left hand and defensive rotations.

Another possibility is Boston chooses to keep all three of these players –assuming Hayward opts-in — and will extend Tatum and Hayward the following season. They have each of these players bird rights. Should they choose to do so, many rumors will be circulated as we move closer to the trade deadline. These will most likely involve either Brown or Hayward, whose play this coming season may determine their future in Boston.