In 1996, The Simpsons aired an episode called HomerPalooza. In one scene, Abe Simpson advises a young Homer Simpson who is singing into the mirror with Barney Gumble.
“I used to be with it,” Abe says confidently in a flashback, “but then they changed what ‘it’ was. Now, what I’m with isn’t it, and what’s ‘it’ seems weird and scary to me.”
Dramatic pause for effect as a wide-eyed Homer listens to his father.
“It’ll happen to you,” Abe tells Homer and Barney.
I used to be "with it." But then they changed what "it" was. Now what I'm with isn't "it," and what's "it" seems weird and scary to me.
It'll happen to you! pic.twitter.com/kxE5zZ8D4X
— Simpsons Daily Glavins (@simpsons_DG) April 10, 2025
Father Time comes for everybody. Still, even worse than the aging process is how younger generations change trends. Hair metal bands phased out after the 80s, tracksuits ended in the 90s, and wearing long-sleeved shirts under polos died in the 2000s.
The traditional point guard died in the 2010s.
For people like me, the new-age score-first point guards are scary. I often feel like the old man yells at clouds when I talk about the roles of a point guard. For me, Isiah Thomas, Gary Payton, Steve Nash, Jason Kidd, Chris Paul, and Mike Conley are point guards.
Players who can understand the game, control the pace, and understand which teammate needs to touch the ball and when. They don’t lead the team in scoring or shots, but they are integral to the success of an organization. They must be emotionally intelligent players who are exceptional teammates.
However, point guards have a vastly different role in the league today. They have handles, bravado, and the ability to make shots.
Simply put, point guards are stars.
Meanwhile, the Wolves have Conley, a true, traditional point guard, a steady hand at the end of his career. They also have Rob Dillingham. The eighth overall pick last year has the flair, the flash, the gregariousness, and the shifts.
Minnesota may need to choose between the new It and the old It this offseason.
Let’s first acknowledge Conley’s 2024-25 season. He played the fewest minutes per game of his 17-year career (24.7). He also had his second-worst season of his career by field goal percentage, shooting just 40.0%. Still, he had his third-best season from the three-point arc at 41.0%. Conley’s 115.5 offensive rating ranked third on the Wolves. His defensive rating of 107.6 ranked fourth among Minnesota’s rotation players.
He led the Wolves in assist-to-turnover ratio (4.25), and his 35.6 assist ratio ranked highest among Minnesota’s players who appeared in over 20 games. Conley posted a positive net rating with every Timberwolves player except Jaylen Clark and Josh Minott. However, Conley only played ten minutes with Clark and three with Minott. His 6.5 assists per 36 minutes finished second on the Wolves among players who appeared in 20 or more games.
Conley had a solid 2010s point guard season. He played enough on defense to hold his own, dodged screens, and attacked when necessary. He rebounded well for his size and boxed out. Conley controlled the pace on offense, getting the ball to players when they needed it. He attacked when asked, was aggressive when he had to, and was a leader.
He had a great season. Twelve years ago, it may have been an all-NBA season.
This is where it gets complicated, though.
In the year 2025, it isn’t enough.
It’s an admission that pains me to type. I am not saying there isn’t a place on the team for Conley. Still, his production isn’t enough. Shai Gilgeous-Alexander, Tyrese Haliburton, and Jalen Brunson were the other three point guards in the conference finals. Steph Curry, Darius Garland, Jamal Murray, and Derrick White were the other point guards in the semifinals.
Point guards raise a team’s floor and ceiling. Of the eight starting point guards in the semifinals, Conley was the only one to score under ten points per game (6.0). White was the next lowest (16.4), and still had over double Conley’s output.
The Wolves must find their next point guard.
In Dillingham, they have the clearest path to revamping the position on the roster. He fits all the boxes of a modern guard: flashy, fast, and can hit shots from anywhere. He needs to work on his defense, but his court vision is next level.
Dillingham is the only Wolves player with more assists per 36 minutes than Conley (6.8). Even in an up-and-down rookie season where he often could not get on the court, he shot 4.1% better from the field. He played at a 3.8 possessions per game more than Conley in terms of pace.
Dillingham showed flashes of being a difference-maker in the NBA. He logged over five assists in seven out of his 49 appearances despite averaging 10.5 minutes per game. He was instrumental in a February 24 fourth-quarter comeback win over the Oklahoma City Thunder, in which he scored twelve points and had five assists.
However, Dillingham occasionally struggled to adjust to the NBA. His 14.4% turnover percentage was the worst among Wolves players who played over 20 games, and his 33.8% three-point percentage was subpar.
At 20 years old, Dillingham spent his rookie season reworking his jump shot, which could explain the poor shooting percentage. It’s also understandable that the speed and size of the NBA would cause turnover issues. However, the Wolves will need Dillingham to be it immediately.
In Conley, the Wolves still have last generation’s perfect example of a point guard. The calm presence that leads the team with intelligence. In Dillingham, the Wolves have the new generation’s version of a point guard. The bet for the Wolves to push themselves over the edge and win a championship next year is that the past and present can mold together seamlessly and provide them with the it factor they have been missing.