At first glance, Tim Connelly gives off a quintessential American “everyman” vibe. He looks and speaks like all your suburban friends’ dads, who look more comfortable with a Miller Lite in their hands standing behind a grill with the perfect brat-to-burger ratio on a Saturday afternoon than he would in a corporate board room.
He’s one of us.
But behind the unassuming, classically midwestern exterior hides the NBA’s mad scientist. Connelly proved his mettle during his nine years in Denver, drafting Nikola Jokic during a Taco Bell commercial and bringing in Aaron Gordon to build a championship team. When he arrived in Minnesota in 2022, Connelly simultaneously integrated himself seamlessly into the Minnesota culture and laid plans to rewrite Timberwolves history while reimagining how teams play modern basketball.
The Rudy Gobert trade that almost everyone in the basketball community initially panned is now a rousing success after the Minnesota Timberwolves blasted their way to the Western Conference Finals on the backs of their two and sometimes three-big system that everyone thought was a relic of the early 2000s. It didn’t hurt the process that Anthony Edwards, who the Wolves drafted before Connelly arrived in the Twin Cities, emerged as a 22-year-old superstar. Still, the personnel Connelly brought in, tied with the system Chris Finch implemented around Gobert and Karl-Anthony Towns, pushed the Wolves into contention sooner than most would have guessed.
In 2022, overhauling a roster of young, scrappy players who had just pushed second-seeded Memphis to six games in a surprisingly hard-fought first-round series was radical. But Connelly saw the matrix and went big when everyone was going small, and the rest is history.
Once the Wolves crashed out of the Western Conference Finals in a flaccid Game 5 performance against the Dallas Mavericks, the basketball universe counted Connelly out again, saying that Minnesota’s cap situation would force it to run it back in 2024-25. All they could do was make some small moves on the margins while entering cap hell that now goes by a different name, the second apron. The new league rules backed Connelly into a corner. The only conventional route to changing the mix and adding talent would be making the difficult decision to move on from KAT and recoup as many assets as possible.
With only the 27th and 37th picks to play with, Connelly and Minnesota’s draft was supposed to be quiet. Still, the mad scientist found a creative way to immediately add talent to Minnesota’s roster without giving up any current assets.
Connelly masterminded the most interesting move of the first round of the draft. Out of nowhere, Shams Charania reported that the Timberwolves had traded for Rob Dillingham, the eighth pick in Wednesday’s draft, who initially thought he was going to San Antonio to throw lobs to Victor Wembanyama. Instead, the San Antonio Spurs sent the 19-year-old out of Kentucky to Minnesota as the heir to the Mike Conley point guard throne. In the minutes after the trade was announced and the details were still murky, some Wolves fans feared the worst. Would this draft day coup come at the expense of a fan-favorite player like Naz Reid or possibly as part of an even bigger move around Karl-Anthony Towns? After a few minutes, Woj tweeted the trade details, and by god, Tim Connelly did it again.
The Wolves sent San Antonio their unprotected first-round pick in 2031 and a top-1 protected pick swap in 2030 for the rights to Dillingham. It’s not nothing. However, after watching the presidential debate on Thursday night, who the hell even knows if we’re going to be around in six or seven years when those picks convey? Assuming we’re still semi-civilized and not roaming the wasteland just yet, it’s a bet on a successful run for the Anthony Edwards-led Timberwolves, one worth making to add a scoring threat who can help the team next year.
I won’t pretend to be a draft expert, especially this year. Still, Dillingham seems to be everything the Wolves needed to add to one of the most talented teams in the NBA. He can be a microwave scorer off the bench. Dillingham shot 44 percent from three in his lone year at Kentucky, and he can give Mike Conley a much-needed rest during the regular season grind.
There are red flags that could derail this move. Dillingham is small enough by NBA standards that he will have to be an outlier to be an above-average point guard. With the volatility of the modern NBA, Connelly could have just gift-wrapped and handed the Spurs the next Victor Wembanyama, who is currently in the sixth grade. And according to ESPN’s Bobby Marks, adding Rob Dillingham will raise Minnesota’s luxury tax bill by almost $30 million. With the ownership dispute between Glen Taylor and Marc Lore and Alex Rodriguez raging in the courts, an extra $30 million for a 6’1” 19-year-old would make any billionaire rethink their choices.
Tim Connelly sees things differently than most career NBA executives, and his creativity will have a lasting impact on this era of Timberwolves basketball. He put the rest of the NBA on notice two years ago when he traded for Gobert, and he may have just done it again with the Dillingham trade.
