Every approach to Kelly Oubre’s upcoming free agency comes with risks

As expected, the Wizards and Kelly Oubre Jr. didn’t reach an agreement on extending his rookie deal before Monday’s rookie extension deadline. Both parties will have to wait until this summer when he becomes a free agent to work out a new deal. The Wizards faced a similar situation two years ago when Otto Porter hit the restricted free agent market and they ended up matching the Nets’ max offer sheet to keep him in Washington.

The question remains now though, which direction will they go with Oubre? They have two options: They can play the market in restricted free agency, or hope they can try to make a proactive trade if they’re worried about locking into a bad deal in free agency. Both options have some potential drawbacks that the team must consider as they try to build towards the future.

Trading Oubre

If the Wizards decide to trade Oubre, it would move the Wizards away from their philosophy of retaining their core players that were drafted and developed to be centerpieces for the future. The idea of moving on from an athletic, 22-year-old wing seems crazy in the modern NBA, but it would signify perhaps that the Wizards were ready to move on from a project player.

Trading him would likely bring some level of value just based on his age and his potential alone, but what the Wizards get in return may not do much to help their financial situation. The Wizards will be over the cap at the start of free agency whether they keep Oubre or not.

So what would be the benefit of trading Oubre? If the Wizards want to trade him for a draft pick, then at least it would reduce the amount of money that they would have to commit next season and beyond. It could also open up playing time for Troy Brown Jr., who they took with the 15th overall pick in the draft this summer. Outside of that, they would need to bring back a player that can be a rotation player at a good value to make a deal worthwhile.

It’s unfortunate that financial implications could drive the ultimate decision on whether or not to keep Oubre at the deadline, but the Wizards’ roster construction and lack of cap flexibility puts them in a position where they have to consider all options.

Entering restricted free agency

The more likely scenario is that the Wizards will end up keeping Oubre for the rest of the season, and he will enter into free agency as a restricted free agent. The Wizards would then have to deal with the potential of he could sign a big offer sheet with another team, much like Porter did during his free agency two years ago.

The summer of 2019 is already expected to be a huge free agency period. Teams like the Los Angeles Lakers, Brooklyn Nets and New York Knicks have already cleared cap space for the possibility of them signing a big name free agent. As we have seen in past years of big free agency periods, the teams that strike out—like the Wizards in 2016—wind up overpaying for lesser players.

What if this same scenario repeats itself? Oubre could have the opportunity to cash in. The Wizards can ill-afford to get into a bidding war. Teams will know that a large contract offer could push the Wizards beyond what they can afford, or force them to make concurrent moves to open up space. Even if they choose to match, the offer sheet can be loaded with burdensome provisions like trade kickers that can complicate things down the road.

The other thing to consider with Oubre’s contract is determining his market. Three players drafted near Oubre in 2015—Myles Turner, Larry Nance Jr. and Justise Winslow—signed rookie contract extensions before the deadline.

Winslow’s three-year, $39 million extension with a team option on the final year, sets an interesting baseline for Oubre’s negotiations next summer. Winslow had a better pedigree coming out of college, but he’s been injury-prone and you can make the case he hasn’t been as productive as Oubre through their first three seasons. Can Oubre fetch a better deal this summer? If so, can the Wizards afford to go that high to keep him? We’ll have to wait and see.

How should the Wizards approach this situation?

The Wizards need to be more decisive than they were during the Otto Porter free agency process. The parameters are not in their favor to allow the market to dictate his value. As we have seen in the NBA time and time again, teams who are desperate for talent will overspend. The Wizards are not in a position where they can afford to see how things play out. Adding another bloated contract to the team’s payroll will make it nearly impossible to add any meaningful talent around that core.

Now is the time to figure out what they think his value is and act accordingly. If they think he’s worth the big bucks and potential luxury tax issues down the road, they need to move swiftly to offer him a big deal before someone offers him a bigger deal. If they’re worried about committing to him long-term they should be working the phones to see if they can find something that makes more sense.

Making the right decision on Oubre will not be easy, but it’s a critical part of putting together a young, cost-efficient team to support John Wall as he enters his super-max years.