The trade deadline is an extremely useful barometer of a team's ability to accurately assess its own circumstances. In general, bad teams should be moving veterans for younger assets, while good teams can afford to be more aggressive in seeking out immediate upgrades. In practice? Trades are often made with unclear motives. The Cleveland Cavaliers wouldn't be desperately trying to trade Andre Drummond right now if they hadn't nonsensically acquired him at the 2020 deadline in the first place. As a general rule, teams sitting 26 games below .500 shouldn't trade for expensive veterans without reason to believe they're close to future contention.
But the 2021 deadline is somewhat complicated. Self-evaluation has never been more difficult in the age of COVID-19, which has in turn complicated every team's ability to plan for the future. Take the Toronto Raptors. On paper, a team nine games below .500 should probably try to move its 34-year-old star point guard on an expiring contract, but Toronto's situation is somewhat complicated. Part of the reason the Raptors are struggling is the depth they lost in an effort to clear our max 2021 cap space. They wanted to use that space on Giannis Antetokounmpo, who has since re-signed with the Bucks. Now, in a weak free-agent class, they might not have any better options than simply re-signing their own top free agents, Kyle Lowry and Norman Powell, and hoping that a return to Canada after a season spent in Florida helps them right the ship next season.
The Raptors may be the only team preparing to cross the border next season, but that doesn't mean they're the only one facing deadline uncertainty. It isn't clear whether or not the following five players are going to be traded at the deadline, but if their teams are honest with themselves about their priorities moving forward, they certainly should be.
1. Victor Oladipo
Houston has so far driven a hard bargain for Victor Oladipo. They are asking for either a good first-round pick or a valuable young player, The Athletic's Shams Charania reports. So far, neither has been offered. In all likelihood, none will be. Oladipo has struggled in Houston, and even teams expecting him to revert to his Indiana form in a winning environment know that they can try to poach him in the offseason for free. Several potential suitors -- such as Dallas, Miami and New York -- will have significant cap space this offseason.
The Rockets can offer Oladipo more money than any other suitor, but will they want to? His health hardly warrants a five-year deal. If they were interested in paying anyone long-term money, they might simply have taken Caris LeVert in the James Harden trade instead of flipping him for Oladipo. Houston is already paying John Wall max money in the middle of a rebuild. That duo has lost the last eight games it has played together, and Kevin Porter Jr. appears destined for a starting role next season. The Rockets hardly have a reason to break the bank here, and even if they're willing to do so, there's no guarantee Oladipo even takes their money if a winner in a big market makes a similar offer.
This is a fairly straightforward case. The Rockets can either move Oladipo now for less than what they'd consider fair value, or they can get no value whatsoever when he walks in the offseason. Unless every offer comes with bad long-term money attached, Houston should pick one on the basic principle that something is better than nothing.
Will they do so? Houston values optics in trade negotiations, and dealing Oladipo for pennies on the dollar would look bad after he was a central asset in the Harden deal. Don't be surprised if the Rockets do wind up trading him for second-round picks, but in the form of a protected first-rounder that is unlikely to actually convey. Their return on the Oladipo investment is going to be significantly lower than they expected when they made the trade, but that doesn't mean they should deprive themselves of any value for a player that doesn't figure into their future.
2. Spencer Dinwiddie
The Nets haven't ruled him out for the season yet, but the odds of Spencer Dinwiddie returning from a partially torn ACL in time to contribute to a playoff run appear slim, and with a player option coming up, his days in Brooklyn are likely numbered. Could the Nets afford to re-sign him? Sure. Joe Tsai is worth over $10 billion. But as expensive as the Nets have become, they have made several financially-influenced decisions that might have hurt their on-court product. Garrett Temple would be a valuable rotation player for them right now if they hadn't declined his $5 million option last offseason. They are one of the few contenders not to use their mid-level exception in 2020 free agency. Even if they want Dinwiddie back, he may walk for a starting job. Brooklyn can't offer him one.