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.