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Danny Ainge, Boston Celtics
The Boston Celtics have rarely missed on draft prospects in recent years. Jayson Tatum, Jaylen Brown and Payton Pritchard all won a championship with the franchise. All three of those players were drafted by the franchise and developed within the team’s system. Sam Hauser was also pinpointed as a high-level prospect after he went undrafted.
However, it has emerged that Boston missed out on a primary draft target in 2019. During a recent appearance on ‘The OGs Show,’ Miami Heat guard Tyler Herro revealed the Celtics had promised to select him. Unfortunately for Boston, the Heat swooped in with the 13th pick. Danny Ainge then pivoted to select Romeo Langford with the 14th pick. Grant Williams was selected 22nd that year, too.
“On draft night, the Celtics had the 14th pick, and they had already guaranteed me the pick for the most part,” Herro said. “And then Miami took me right before at 13, so it was a blessing.”
Herro has developed into a highly skilled, offensive-minded guard. In 2022, he won the Sixth Man of the Year award. This season, he’s averaging 23.6 points, 5.6 rebounds and 5 assists while shooting 46/9% from the field and 40.1% from three-point range. Most importantly, Herro has been the Heat’s best player over their first 35 games of the season.
On the other hand, Langford is currently out of the NBA, having struggled with the Celtics and San Antonio Spurs.
Celtics’ Guard Depth is Elite
It’s hard to imagine Herro on this current Celtics roster. The rotation of Derrick White, Jrue Holiday and Pritchard is arguably the best guard trio in the NBA. Herro’s presence would likely mean that Pritchard never got drafted by the Celtics or that he never developed into the player we’re seeing this year.
Still, Herro’s ability to score the rock, create for himself and create for others would undoubtedly have improved Boston’s roster, both back in 2019 and in the present. The Celtics are unlikely to have any regrets over how things played out. After all, they won a championship this past season. Still, seeing Herro thrive in Miami likely hurt.
Payton Pritchard Didn’t Expect Celtics to Draft Him
While Herro came into the 2019 NBA Draft expecting to fall to Boston, Payton Pritchard didn’t envision himself landing with the franchise. Pritchard was selected with the 26th pick in the 2020 NBA draft.
“I remember the whole thing,” Pritchard said during an appearance on “The Young Man and The Three” podcast. “I didn’t even think I was gonna go to Boston, cause I was looking at their roster too and I’m like they’re guard-heavy. They picked two point guards in the draft before and I didn’t even work out for them or anything.”
Pritchard is on track to contend for the 2025 Sixth Man of the Year award. That would allow him to match Herro’s success, only with a championship also on his resume. Pritchard, like Herro, is currently enjoying his best season to date.
Given how things worked out for Boston, it’s fair to assume Pritchard was the final parting gift from Ainge. He left the franchise shortly after and is now working with the Utah Jazz as President of Basketball Operations.
Adam Taylor is a basketball reporter covering the Boston Celtics and Phoenix Suns for Heavy. He has also written for CelticsBlog, USA Today, Yardbarker and FanSided. Adam has a bachelor’s degree in creative writing from Open University. More about Adam Taylor
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