It’s been 16 years since Doc Rivers stood tall at the helm and was drenched with Gatorade at TD Garden in the concluding seconds of the 2008 NBA Finals, becoming a first-time champion with the Boston Celtics.

Five years later, Rivers joined the Los Angeles Clippers and avoided the rebuilding stage with the Celtics, commissioned by then-general manager Danny Ainge. It wasn’t a move that went well-received in Boston as Rivers inherited a stacked “Lob City” Clippers team featuring Chris Paul, Blake Griffin, Jamal Crawford and JJ Redick, while Boston bit the bullet and stepped out of the competitive circle.

That career move didn’t pan out for Rivers or the Clippers at all, and early on Rivers himself began to feel regret in turning his back on the Celtics in search of greener pastures.

“Listen, in my first year with the Clippers I said, ‘Uh-oh, I may have made a mistake,'” Rivers told Steve Bulpett of Heavy. “But, you know, one thing I’ve never done is I never look back. I just don’t. I’ve never done that.”

Rivers, despite being handed arguably the most talented roster (on paper) in the Western Conference, routinely turned the Clippers into an underachieving disappointment. Under Rivers, Los Angeles went 3-8 in potential series-clinching playoff games, tying Rivers for the worst mark by an NBA head coach with a single team ever. The Clippers blew a 3-1 lead over the Denver Nuggets in the 2020 conference finals just before Rivers stepped down and departed Los Angeles.

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The results weren’t what Rivers envisioned, not to mention the dramatic 2014 fallout with ex-Clippers owner Donald Sterling, who was forced to sell the franchise to Steve Ballmer and slapped with a lifetime ban from the NBA.

“The lesson that you learn is that you can’t play through a bad organization, you know?” Rivers said, per Bulpett. “I left the best organization in basketball at the time to go to the worst organization in basketball, and you can’t outrun that. You can’t beat that. And I realized it early.”

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The Celtics, during the Rivers run in LA, stuck by the process of their rebuild. Boston turned the draft selection returns from its Paul Pierce and Kevin Garnett trade with the Brooklyn Nets into Jaylen Brown and Jayson Tatum. Brad Stevens replaced Rivers in 2013 and was promoted to the head honcho of the front office eight years later, striking notable deals for Kristaps Porzingis and Jrue Holiday.

Fast forward 11 years after Rivers bid Boston farewell and the Celtics captured Banner 18 with a window to add more titles for the next few years.

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Rivers now has a front-row seat as head coach of the 1-4 Milwaukee Bucks, looking up at the Celtics and what could’ve been had he stuck around.

Featured image via Paul Rutherford/Imagn Images