The Cleveland Cavaliers felt a chill go down their spine when the Boston Celtics just adjusted their trade with the Portland Trail Blazers. Jrue Holiday was initially supposed to net the Celtics Anfernee Simons and two second-round picks, but Holiday's failed physical caused the Blazers to renegotiate the terms of the deal and keep both picks.
That sounds eerily similar to a trade eight years ago, when the Celtics traded a guard away and had to adjust the trade because of that player's injury. That trade may have been the absolute worst deal in franchise history. The guard in question? Isaiah Thomas.
The Cavaliers went through with a terrible trade
Kyrie Irving demanded a trade. Coming off of three-straight trips to the NBA Finals, including an iconic seven-game NBA Finals victory and the only trophy of his career, Irving forced the franchise to trade him. Tall tales abound as to how that process played out behind closed doors, but it is commonly thought that the All-Star point guard threatened to get surgery and miss the entire season.
Cleveland was fully in the midst of its run of contention with LeBron James, still possibly the greatest player alive, and didn't feel that it could afford to be patient. With their leverage dissolving and the clock ticking, they worked out a trade with the rival Boston Celtics: Kyrie Irving to New England, a package built around Isaiah Thomas and a premium first-round pick to the Midwest.
Thomas was coming off of an All-NBA season where he finished fifth in MVP voting, so on the surface it seemed like a strong return for Cleveland. Yet when Thomas reported for his physical with the Cavaliers, red flags were raised. Something came up in the physical that had Cleveland balk and head back to the negotiating table.
The Cavaliers couldn't get Boston to include another first-round pick, so they had a decision: back out of the trade altogether or accept a second-round pick. Whether they felt the other offers out there weren't worth making, or they didn't want to fact the awkwardness of unraveling the deal, they decided to move forward with a 2020 Miami Heat second as compensation for the state of Thomas's physical.
They probably should have backed out, no matter the consequences. Thomas was a disaster in Cleveland, clearly hampered by his hip injury and unable to provide secondary scoring beside LeBron James and Kevin Love. He played just 15 games for the Cavaliers, shooting a glacial 36.1 percent from the field and 25.3 percent from 3-point range. The Cavs had no choice but to dump him at the Trade Deadline to have a chance at a playoff run.
The first-round pick became No. 8, not quite the premium pick the team was hoping for, and they used it on Alabama guard Collin Sexton (imagine if the pick had landed in the Top 5 and names like Luka Doncic, Jaren Jackson Jr. and Trae Young were in play? As it was the Cavs still could have drafted Shai Gilgeous-Alexander or Mikal Bridges at eight).
That Miami second? It was tossed out to make one of those midseason desperation trades happen, so Cleveland never got to use it.
There were trades that the franchise made in the 1980s that were so bad the NBA wrote a rule to prevent teams from being that stupid. Multiple franchises owe their success in that decade to the Cavaliers' diasastrous deals. But those trades were made by mediocre teams; the Cavaliers blowing the Kyrie trade broke down a title contender.
Portland may regret this trade
Now the Portland Trail Blazers are moving forward with their version of such a trade. Hopefully, for Portland and for basketball fans, Jrue Holiday's injury is not serious. Everyone wants to see him healthy and locking down opposing players.
Yet if not, and if this is the end of Holiday as a star-level player, Portland may regret going through with this trade. Getting back a pair of seconds is fine, but trading a young scoring guard in Anfernee Simons for an albatross contract and a hobbled former star can cripple their ability to build a perennial playoff team in the Pacific Northwest.
Just ask Cavaliers fans. Going through with a trade for an injured player can haunt you.