A Tough Finish To a Great Season: 2019–2020 Boston Celtics Final Thoughts

Here are a few hypothetical questions to ponder as the Miami Heat prepare to take on their former hero LeBron and the Los Angeles Lakers in the Bubble Finals on Wednesday.

  1. If Gordon Hayward were even 85% healthy, rather than the 60–70% we saw over the last few games, would that have been enough to keep the Celtics from wilting in the 4th quarter? They weren’t quite deep enough, that seems pretty clear.
  2. If the Celtics won the pre-draft coin flip and landed Tyler Herro at pick 13, and Miami chose Romeo Langford at pick 14, would that have flipped this series in Boston’s favor? Would Herro have had a similar impact off the Boston bench? He certainly would’ve had the same opportunity.
  3. If the playoffs had been played in April, May and June, would the Bucks have beaten the Heat, and then would the Celtics have beaten that 70-win-pace Bucks team in the East Finals?
  4. If Bam Adebayo doesn’t block Jayson Tatum’s dunk in Game 1…or if Game 2’s second half Celtics meltdown was just a bit less melty…or if Tyler Herro misses just a couple more shots in Game 4…or if Andre Iguodala didn’t find the way-back machine in Game 6 and hit every shot he took…we would be waiting for Game 7 on Wednesday. But those things all happened and here we are.

Stepping back from the hypotheticals, its important to consider the grand scheme. The Celtics are nowhere near a crossroads in their title hopes. Despite two conference finals appearances in the last three years, they are still at the beginning of the proverbial title road. Appreciate how far they came and how well they meshed together this year. After last year, this year was pure oxygen.

A few months and then…another season!

Finding one more shooter — -or turning Grant Williams into a corner-3 shooting-big, like a younger PJ Tucker — would be excellent.

Getting Gordon Hayward healthy for what may be his final year in Boston would be excellent.

Getting 20 minutes per game out of Romeo Langford to see if he can turn into a playmaker and develop his handle, passing and range..that would be excellent.

We’ve only seen glimpses of how good Robert Williams can be defensively..but he needs to learn to read the game with experience. A solid passer, maybe Brad can find Williams initiating at the top of the key like Bam — or at least see if that can work a few times a game against weaker opponents. A 15-footer from the baseline (think Tony Battie!) would be excellent.

Celtics impending free-agents

Hayward and Kanter have player options. Kanter could test the market, but I doubt it.

Brad Wanamaker, Tremont Waters and Tacko Fall are restricted free-agents. Hopefully nobody offers Wanamaker or Fall a two-year deal, but it’s very possible.

Semi Ojeleye has a team-option.

After next year, Daniel Theis will be an unrestricted free-agent.


The Jayson Tatum max extension is the next item of business for Ainge. Tatum would be a restricted free-agent in the summer of 2021. If the Celtics can get that out of the way, they’d have a better sense of their cap room before October 18th- the start of free-agency.

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