And that's something that has stayed with him even as he leaves town.
On Friday, the Cavs traded Hill to the Milwaukee Bucks in a three-team deal that included 2016 NBA champion Matthew Dellavedova returning to Cleveland. As he said goodbye to the Cavs, Hill extended an apology, via The Athletic's Joe Vardon, for missing a potential game-winning free throw against the Golden State Warriors at the end of Game 1 of the 2018 NBA Finals:
"Sorry I couldn't get it done when I was here for the Finals, missing that free throw, but it's nothing but love. You gotta give the organization thank you, you gotta give my teammates a huge thank you for welcoming me with open arms since I first got here, giving me a chance to play in the NBA Finals, something I've never dreamed of. So for me it's kind of bittersweet.
"You don't want to leave a place that you create relationships with your teammates and people in the organization, front office and things like that, but, it's a business. Get another opportunity to take my talents and my game down to Milwaukee and try to help them win games as best as I can."
Hill was acquired by Cleveland prior to the trade deadline in February. Little did anyone know at the time, the veteran would wind up being involved in one of the franchise's most devastating moments.
With the Cavs down by one with 4.7 seconds remaining in Game 1, Hill stepped to the line with a chance to come through in the clutch for his team. He sank the first attempt to tie the game, but with a chance to give his team a one-point lead in the final seconds, he couldn't convert—and that led to the JR Smith debacle:
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Cleveland would go on to lose 124-114 in overtime despite a 51-point performance by LeBron James. Golden State went on to sweep the series, 4-0, to win its third title in four seasons against the Cavs.
It was later revealed that James suffered a hand injury as the result of him punching a whiteboard after the Game 1 meltdown.
Fair or not, Hill's time in Cleveland will always be remembered by the missed free throw. Not because of his miss necessarily, but because of what followed.
Hill was not the one who mistakenly ran out the clock in a tie game, nor was he the reason the Cavaliers lost the Finals. The Warriors—led by Stephen Curry, Kevin Durant, Klay Thompson and Draymond Green—are one of the greatest teams ever. Had Hill made the free throw, it's possible Golden State would have hit a last-second shot for the win. But even if Cleveland had won Game 1, there's no telling how competitive the rest of the series would have been.
This is not the first time this season Hill has addressed the situation. Last month, he revealed to The Athletic's Jason Lloyd that his unfortunate miss "bothered" him all offseason:
"You're a little depressed at first because as a player, as a competitor, you put the blame on yourself a little bit. All summer it kind of bothered me. If I hit that free throw, would it have been a different series? Or would it just have been 4-1? It's getting a win instead of getting skunked. But if it's 4-1 then it really doesn't matter about one f--king game. But who knows? I hit that, the pressure is on them now. Maybe it's a different series."
Hill now moves on to his sixth team. The 32-year-old guard averaged 10.8 points and 2.8 assists in 13 games for Cleveland this season.