We’re about a month out from the trade deadline, and NBA Trade Machine proposals are already starting to run amok on my timeline. As we enter a new chapter of the season, I figured it would be a good time to get some ground rules out of the way. Let’s go through how this part of the season generally works today, and then tomorrow I’ll lay out several trade targets. We’ll bring in Canis contributor Jack Borman, who will offer a few quick thoughts on the financial implications of a trade for each player, and lay out a potential trade package.

General Trade Season Notes

While trade season doesn’t really kick into high-gear until we get a bit closer to the February 10th trade deadline, the Cam Reddish trade between the New York Knicks and Atlanta Hawks felt like the unofficial kick-off to trade season. The bigger dominos won’t fall yet, but teams are starting to be more active.

The trade deadline is an important checkpoint for every team in the league. It forces front offices to evaluate every player on their roster individually, as well as the sum of those parts, and where their organization is headed both in the short-term and the long-term. Basically, it forces franchises to take a look in the mirror.

For some teams, the trade deadline is simple. If you’re at the top of your conference, you’re looking to shed dead weight and find a way to improve your chances of winning a championship. In general, draft picks aren’t as valuable to these teams, or they’re at least more willing to include first-round picks with lighter protections if it means they’re going to get closer to winning the championship. On the opposite end, you have the tanking teams, who are open for business, and generally are willing to move veterans and take on bad money in exchange for future assets.

Then, there’s everyone else. The play-in tournament has muddied the waters even further on who will do what at the deadline, and in many cases, it becomes an eye of the beholder situation. In many ways, this is where the good, strong organizations separate themselves from the bad ones. Being able to honestly assess your roster and future is important. It’s better to admit that a pick or signing was a failure and move on than to pridefully wait for an upswing that’s never going to happen. This is known as loss aversion bias.

There’s plenty to criticize Gersson Rosas for, but I give him credit for recognizing that it wasn’t going to work out for Jarrett Culver in Minnesota, and cutting his losses this off-season. Being willing to admit defeat on that particular draft pick brought Patrick Beverley to Minnesota.

With that in mind, the Timberwolves fit into this middle-ground of teams who could go several different directions at the trade deadline. We always assume that teams are trying to upgrade, and the Timberwolves surely are. But just how aggressive should Sachin Gupta be?

Timberwolves Trade Deadline Philosophy

This seems like an obvious statement, but it’s important to remember that nothing comes free. If your trade proposal in the NBA Trade Machine doesn’t sting a little, it probably isn’t very realistic. To make a small upgrade, you generally have to give up something small. To make a big upgrade, you generally have to give up something pretty substantial.

There are exceptions to every rule, but it’s worth noting that throwing Jake Layman and Taurean Prince’s expiring salaries into every deal isn’t going to bring in a legitimate wing player without attaching something noteworthy.

On that note, I understand that it is capital-S SCARY to imagine the Minnesota Timberwolves giving up future assets given the fact that this organization has practically been written in pen in the lottery for the past 15 years. If something meaningful is going to be done here, we’re going to have to be able to stomach that.

(Editor’s note: this guy will help us stomach that, though...)

Photo by Joe Murphy/NBAE via Getty Images

Thursday’s loss at Memphis exposed just how top-heavy this roster is right now. While Jaylen Nowell has come on of late to have a nice season, his absence should not render bench units completely incapable of scoring. The regression/poor shooting from Malik Beasley, Jaden McDaniels, and Naz Reid has made a team that looked deep-ish on paper heading into the season much more top-heavy.

Unfortunately, I fear that the shooting this season from McDaniels and Reid are likely closer to their true shooting talent than last season in empty gyms. In fairness, both players operate on relatively low volume, so a few makes/misses here or there impacts their percentages more drastically than Beasley.

As for Beasley, I don’t know, man. I’m as big of a Malik Beasley fan as there is, and I really want to believe that he’s going to break out soon. I just don’t know how patient Sachin Gupta will be, or should be. He has a long history, with a large sample size, of being an elite shooter, but this doesn’t feel like a player who is simply getting unlucky. His shot is much flatter this year than last, and while that’s easily correctable, it’s impossible to predict when that will be corrected.

At the end of the day, the Timberwolves should be open to shopping any of those guys, and their goal should be to improve the talent level of the team. They have graduated from “bad” to “frisky”, and with an upgrade here or there would be a legitimately good team. The nice thing is that the current starting lineup gives them a lot of options. They don’t need to look for an upgrade in the starting lineup, but adding a starter-level player would coincidentally improve their bench play as well.

I suspect that Minnesota is open to trading somewhat significant future assets at this trade deadline, with the kicker being that they’ll only make that type of move for someone they envision being around for the long haul. They’re not trading future firsts for players on expiring deals, but if the long-term fit is right, they’re willing to be aggressive and pull the trigger.

Lastly, there’s been a lot of reporting that the Timberwolves are still looking for a front court partner for Karl-Anthony Towns despite the breakout from Jarred Vanderbilt. As I’ll probably mention roughly 20 times tomorrow, I don’t think that looking for an upgrade at forward automatically means Vanderbilt loses his spot in the starting lineup. Vando has proven to be an outstanding wing defender, so any big wing/forward who can shoot would theoretically fit alongside both Vanderbilt and Towns.

I’d say it’s likely that Patrick Beverley’s spot in the starting lineup is safer than Vanderbilt’s, but I think there’s a real argument to be made that the opposite should be true. Beverley could help stabilize the second-unit, and it would make it easier to control the minute-load of the 33-year old.

Really, that’s where I see the vision for this team heading, if they’re able to capitalize at this trade deadline. Finding a forward who can capably play on the wing on offense and is able to defend 4s on defense makes the pieces of this team fit seamlessly. You’re able to truly weaponize Vanderbilt on the wing full-time defensively, while maintaining stronger interior defense, and you keep Beverley fresh.

Either way, Gupta has a lot of options. It’s exciting to imagine which route he may take.