Welcome to the Worst Trades for Each Team in NBA History— a series of stories that looks at arguably the most disastrous move made during a franchise’s time in the league. Per team, we’ll nominate two deals and look at who and what were involved in the trade, the immediate consequences of the move, and the long-term implications it had for whichever teams took part.
These deals are justified as the “worst” using historical context and analyzing what happened because of the trade.
Staff Writers Yazin Ahmed and Dominic Chiappone contributed to this article.
The Worst Trades in Heat History
Dominic Chiappone: A major what-if
Trade details:
- MIA (doesn’t) receive: four first-round picks, as many as six picks
- BOS (doesn’t) receive: Justise Winslow
Explanation:
This is quietly the toughest team to find a “worst trade” for in this division. Most of Miami’s moves came via terrible free-agent signings and contract extensions.
So, how about we pick a non-trade?
In 2018, NBC reported that Boston during the 2015 draft offered as many as four first-rounders and six total picks for Miami’s No. 10 selection that year. That same offer was also given to Detroit and Charlotte, who were picking around Miami. All three said no to Boston’s offer.
Did that actually happen? It’s hard to say. Yet, talk about avoiding disaster for Boston. The Celtics were rising after the Paul Pierce and Kevin Garnett era. Boston easily remains one of the top-five or so teams in the league over the past decade in most seasons. A move like that would’ve completely derailed all that success since the mid-2010s.
And then, there’s the Miami side. The Heat ended up taking Justise Winslow. He lasted five years, then found his way to Memphis, Los Angeles and Portland from 2021 until 2023. He fell to the G League last year. For now, his best accomplishment was finishing sixth in Rookie of the Year voting.
Yazin Ahmed: Oh my Bosh!
Trade details:
- MIA receives: Chris Bosh (S-&-T, 125M/6 years)
- TOR receives: 2011 FRP (via TOR), 2011 FRP (via MIA), $16.5M trade exception
Explanation:
Shoutout to the man, the myth, the legend Pat Riley for not having any awful trades. That shows just how successful he’s been at making trades but not as successful in accepting the ones he’s been offered (mentioned by Dominic above). This one requires some deep trade analysis and will be all over the place so hang on.
The 2010 NBA free agency class is arguably the greatest ever, being a face for modern free agency classes and one of the reasons was Chris Bosh. The multiple-time All-Star big was a premier asset on the market, with teams wanting him badly. Eventually, Bosh agreed to a deal with the Heat, but it became a sign-and-trade. This allowed him to earn $125M over six years instead of only 96M over four if he signed regularly.
To make a sign and trade work, Miami had to surrender assets.
This is where the mess-up began. Miami sent a $16.5M trade exception, their 2011 FRP and Toronto’s own FRP in 2011 back. Miami owned control of this pick from the Jermaine O’Neal and Shawn Marion swap a few years back, but the pick was lottery-protected.
What if?
Let’s hypothesize a little.
If they didn’t give Chris the S-&-T — something he probably would’ve been fine with — they keep both FRPs. Their pick became Norris Cole, who Toronto negotiated to send back to Miami but ultimately made the Heat lose the 31st pick, Bojan Bogdanovic.
The Toronto FRP would’ve been free of protections by 2014. In 2014, if Miami would’ve kept Toronto’s pick (it was lotto-protected), they would’ve held the 20th selection. Toronto originally took Bruno Caboclo, but Miami would’ve likely used this pick on either Kyle Anderson, a win-now piece that would’ve been pretty solid on future rosters, or Shabazz Napier, someone who LeBron James was a big advocate for the Heat to take.
The Heat were required to then move their 26th pick (PJ Hairston) plus additional assets (one of them would become NBA rotational wing Jaylen Nowell) for pick 24 to select Napier. So hypothetically, if they don’t make the sign and trade, they keep pick 20 and likely take Kyle Anderson or Shabazz Napier. And at pick 24, it’s not unlikely they look for a backup big and select potential Swiss big man Clint Capela, as the team lacked rebounding off their bench. Toronto never used the TPE in any form, but Miami messed up pretty badly by giving up so much for a simple sign-and-trade deal.
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