Tim Connelly is no stranger to big trades. Look no further than the deal he made for Rudy Gobert just months into his tenure as the Minnesota Timberwolves' decision-maker, or the subsequent trade of Karl-Anthony Towns that split up the big man duo and brought in Julius Randle and Donte DiVencenzo.
The president of the Timberwolves won't hesitate to pull the trigger on another blockbuster deal if something comes to fruition during the 2025-26 season.
Is another Timberwolves trade inevitable?
The Timberwolves have made the Western Conference Finals in back-to-back seasons, and for the most part, they are heading into the upcoming season with the same roster. Nickeil Alexander-Walker is the only sizeable roster departure, but the starting five and much of the depth are still intact.
With two straight deep playoff runs, the Timberwolves are in the midst of the best stretch in franchise history, and they are clearly one of the best teams in the Western Conference. However, their inability to push through and reach the NBA Finals over the last two years has some believing their ceiling as currently constructed is capped, and the loss of Alexander-Walker certainly won't help Minnesota take the next step forward.
Point guard would likely be the position Minnesota would look to upgrade
The point guard position is a particular place to look at if the Timberwolves decide to reconstruct the roster via trade, which is something that Jon Krawczynski hinted toward being a possibility.
Krawczynski said via The Athletic, "What I do know is that if the point guard is not solidified and the rest of the team looks primed for another deep playoff run, Connelly will not hesitate to pull the trigger on a big trade. That is the way he’s built these Wolves, and it won’t stop now,"
Mike Conley is still the starting lead guard in Minnesota. While he has been a vital piece of the team since becoming yet another big Connelly trade addition, he is close to 38 years old and clearly well past his prime. Furthermore, it is unclear if Rob Dillingham will develop enough to become a reliable guard option in his second season. There isn't much point guard depth to write home about after those two.
Point guard is such a crucial position for the Timberwolves because they employ Anthony Edwards, one of the best players in the NBA. Ensuring the table is set for him in his spots is immensely important.
The team also has Gobert, a big man who offers next to no creation ability, but one who can finish lobs inside. A catch-and-shoot threat like DiVencenzo would similarly benefit from improved point guard play if performances from Conley and Dillingham are not up to par.
It isn't clear which guards, if any, will be available on the trade market this season, nor do the Timberwolves have an obvious trade candidate to send away. They are still deprived of picks from previous trades, too.
However, their championship window is now, so the team would likely be okay parting with youngsters like Dillingham, Terrance Shannon Jr., and Joan Beringer if it meant adding the player who could get them over the hump. Connelly seemingly always has something up his sleeve, and he surely wouldn't hesitate to make a huge trade if something materialized.