The Kyrie Irving Trade That Almost Never Happened

When Kyrie Irving decided to request a trade from the Cleveland Cavaliers, the Boston Celtics weren’t even on his mind.

In fact, that’s a poor choice of words. He didn’t want to play for the Celtics at all.

The Kyrie Irving Trade That Almost Never Happened

When Irving asked to moved, his “then-agent, Jeffrey Wechsler, informed (Cavs owner Dan Gilbert) that his client preferred to be dealt to either the (San Antonio) Spurs, (New York) Knicks, (Minnesota) Timberwolves or (Miami) Heat, with the list intentionally excluding the Celtics…,” per Yahoo Sports insider Jake Fischer.

Yet, Wechsler failed to follow his client’s instructions. Indeed, “…once Wechsler secured permission from Gilbert to contact opposing teams… he and then-Celtics president Danny Ainge engaged in frequent dialogue about Irving’s trade market.”

Gilbert, decided he didn’t care about Irving’s preference either. “Cleveland’s front office valued the 2018 (Brooklyn) Nets draft pick that Boston held… as a top-five pick in that upcoming draft…,” per Fischer.

As it turns out, the first round pick that the Cavs received from the Celtics did turn out to be a lottery pick. However, it wasn’t a top-five selection. With the No. 8 pick in the 2018 NBA Draft, Cleveland selected Alabama’s Collin Sexton.

Sexton was an explosive scorer who had made a name for himself through high school and college. However, his lack of playmaking instincts doomed him. In 2022, he was traded just a year after averaging a career-high 24.3 points per game. As the Cavs landed a multi-time All-Star in Donovan Mitchell, there’s a line of thought that it all worked out for Cleveland. Yet, the Cavs didn’t just trade Sexton for Mitchell. Cleveland’s also sent Lauri Markkanen and five first-round picks to the Utah Jazz.

Put in perspective, it’s clear why the Cavs are so keen to hold onto Mitchell. He’s played great in Cleveland, having back-to-back career seasons. He helped them win a playoff series without LeBron James for the first time in 31 years.

Yet, they also gave up so much to get him that they want to see work. In that same vein, they’re unlikely to get the assets they’d want in trade return for Mitchell. Just break even, they’d have to receive five first-round picks, an All-Star-caliber player, and a high-end starter.

The Kyrie Irving Trade That Didn’t Happen

Had the Cavs traded Irving to the Knicks, who had the No. 9 pick, Sexton could have still landed in Cleveland. The Brooklyn Nets had both D’Angelo Russell and Caris LeVert, so they didn’t necessarily need a backcourt player. If they were willing to wait, they may have even gotten New York’s No. 3 pick in the 2019 NBA Draft. With two top-five picks, they may have positioned themselves to draft Murray State product Ja Morant.

Those hypotheticals aside, Irving was almost traded to the Knicks anyways. However, instead of Cleveland making the deal, it would’ve been Boston.

“The Celtics once dreamed of pairing Irving with Anthony Davis,” per Fischer. “But… when New York’s front office began to quietly pursue deals to move on from (Kristaps) Porziņģis, the Celtics and Knicks even held tangible dialogue about swapping Irving for the 7-2 sharpshooter…”

Had the Celtics and Knicks agreed to this deal, Brunsonmania may have never happened. Jalen Brunson is so talented and determined that he could’ve had a star turn with the Dallas Mavericks or elsewhere. Yet, few franchises have a hype machine like their market and fan base. This has been as important to Brunson’s breakout as his own ability.

Nonetheless, the Knicks would’ve become a playoff team a little earlier. With a core that’s not too dissimilar to the one they currently have, New York’s Cinderella story could’ve began in 2019. Irving and Julius Randle would’ve been an elite 1-2 punch. Interestingly, it’s unlikely RJ Barrett would’ve been drafted by New York. Their record likely would’ve been too good for a top-three pick. However, a prospect with a similar skillset but more dogged defense —Kentucky product Keldon Johnson —was available until pick No. 29.