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Chandler Parsons? Hassan Whiteside? Demarre Carroll?

Big Country, maybe.
I think it was the most damaging contract ever.

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Reeves's contract was pretty bad. Juwan Howard with Washington was one of the top 5 salaries in the league for almost half a decade and never played close to that level.

Gilbert Arenas deserves a mention

[Edit: got caught up in idea of worst contract and forgot about max. Max is somewhat of a loose term, contextual. Going back further with less contraints, Bulls paid MJ alone significantly more than the cap. I guess '99 on is the "Max" era. I'll leave my musings on worst contract anyhow ...]

Conceptually from the beginning - i.e. something akin to most irrational, where you can't see what the team could have expected or worst as it transpired (injuries, personal issues, unforeseeable declines etc).

On the former far from comprehensive process but giving Jerome James 30 million over 5 years (6 mil a year, starting at 5mil in a season with a $49,500,000 cap. This player has a reputation for being fat, lazy, disliked in the locker room. Production poor and trending down and impact (based on glancing on-off) trending down and now in a weak place. And the player couldn't play full time even if they improved because they average 7.6 fouls per 36 minutes (previous season, roughly in line with career norms) so related to this managed a career high 1330 minutes, and near high 16.6mpg so you need another center higher on the depth chart. Oh and coming off age 29 season you feel the need to give 5 years.

There'll be more harmful but this one came to mind as far as ... what were you thinking?

Didn’t Jon Koncak get a max contract?