Advancing in the first-round in each of the past three seasons and making two conference finals appearances, the Minnesota Timberwolves have been on the brink of winning a championship. It's fair to wonder, though, if things would have been different if they had one of the best ceiling raisers of all-time: Jrue Holiday.
New Portland Trail Blazers head coach and former Wolves assistant Micah Nori said that Holiday told him Minnesota would have won a championship with him on the team in at least one of the three years.
“Jrue did tell me if he was on one of our Minnesota teams the last three years — any of those teams — we would have won a championship,” Nori said.
That stings a bit, doesn't it? Thankfully, the Timberwolves' championship window isn't shut, so we can enjoy this for what it is: a really fun what-if.
The Timberwolves could have won a championship if they had Jrue Holiday
The common theme of the Wolves' past three playoff exits has been a lack of ball-handling and creation alongside Anthony Edwards. Holiday could certainly have helped fill this void, while fitting in like a glove on defense. Whether it's defense, ball-handling, playmaking, creation, or shooting, Holiday gives you a little bit of everything.
By looking at Holiday's raw counting stats, you might think this claim is far-fetched. Regardless, he's a connective guard who impacts every facet of the game in a positive way, and it's not like the Wolves were that far away from winning it all.
This is, in short, what makes him such an impactful all-around player and the ultimate ceiling raiser. We've seen Holiday prove to be the missing piece on two championship teams (the 2021 Milwaukee Bucks and the 2024 Boston Celtics). As such, he could have been the Wolves' missing piece in one of the three past seasons.
Since he was traded in 2023 and 2025, the Wolves, ironically, could have landed him twice. Now, it's hard to pinpoint what their package would have looked like and the ripple effects of trading for him. However, if Holiday was hypothetically plopped onto one of the Wolves' past three teams, things might have looked different.
2024 was the best chance the Wolves have had to win it all in the past three seasons. Yes, they lost in just five games to the Dallas Mavericks in the Western Conference finals, but three of these losses were by single digits. It's not far-fetched to say Jrue could have flipped this series.
Considering the Celtics won the championship with Holiday as a critical part of their success, this part of the hypothetical goes into the butterfly effect a bit. Hypothetically speaking, though, if Holiday were on the Wolves and not the Celtics, I, for one, think there would be an NBA Championship banner in the Target Center right now.
And if Holiday arrived on the team in the offseason of 2024 or 2025, it's also possible that he would have gotten them over the hump.
The Timberwolves' losses were far less close against the San Antonio Spurs this past season and the Oklahoma City Thunder the year before. Nevertheless, with Holiday, they would have been an entirely different team on both sides of the ball, and it's possible he'd move the needle that much.
Ultimately, though, 2024 would have been the clearest year where Holiday's would have changed things for Minnesota.
Timberwolves fans shouldn't lose sleep over this "what-if," and with LaMelo Ball in the mix, it's possible Minnesota gets over the championship hump soon. Thinking about what Holiday would have looked like on recent Timberwolves teams is a fun exercise, though.
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