3 variations on the mythical Hassan Whiteside trade. Which is best?

Truth be told, I’m not worried about the Blazers right now. Terry Stotts, Damian Lillard, and CJ McCollum — yes, he’ll snap out of his slump and everyone will love him by Thanksgiving — are too good for the wheels to totally fall off. They’ll hang around the bottom half of the playoff hunt until the All-star break and then hopefully we’ll all catch Nurk Fever again and things will be fine.

Even if, god forbid, the wheels do totally fall off it doesn’t alter the long-term outlook for this team. It will suck to lose a year of Dame’s prime, but we already know that the Lillard/Nurkic/McCollum core is here to stay, Anfernee Simons and Zach Collins are next in line, and that the bench needs reinforcements. I.e. Anthony Tolliver, Mario Hezonja, and Skal Labissiere aren’t going to cut it as integral cogs in the rotation of a contender. Nothing is going to change those realities between now and July 1, 2020.

One decision, however, does have the potential to alter the long-term makeup of the roster: The Hassan Whiteside Trade.

The options around Whiteside have been presented primarily as “will he be traded?”, but general manager Neil Olshey actually has three distinct options, each with differing pros/cons. Let’s take a look:

Option 1: Let Whiteside’s contract expire

The simplest option is to do nothing and let Whiteside’s $27.1 million contract expire at the end of the season.

Pros: In this scenario the Blazers will have $91 million in guaranteed salary next season and could have up to $18 million in cap space if they let both Kent Bazemore and Labissiere walk as free agents and both Rodney Hood and Hezonja decline their player options. That money could be used to take back a player with a large contract in an unbalanced trade or sign a free agent outright.

Cons: Having $18 million in cap space would be great but the tradeoff is losing Bazemore and Hood — two solid role players who Portland could likely retain on fair, tradeable contracts. Not ideal. The cap space would need to be used to acquire a true needle mover to justify losing those two players.

If Olshey does have an unbalanced trade in mind, Bazemore or Hood could possibly be retained reducing Portland’s cap space to $10ish million. But, as I outline here, there are diminishing returns to having cap space roughly equivalent to the full Mid-level Exception (MLE).

Cap space converted into a starter quality forward hypothetical scenario:

Starters: Lillard, McCollum, Nurkic, Collins, [Player acquired into cap space]

Bench: Simons, Little, Gary Trent Jr., Labissiere on minimum deal, [$5 million room exception], 2020 draft pick, MAYBE Hood or Bazemore

Cap space doesn’t yield a needle-mover and Bazemore/Hood both re-up:

Starters: Lillard, McCollum, Nurkic, Collins, Hood

Bench: Simons, Little, Trent Jr., Bazemore, Labissiere on minimum deal, 2020 draft pick, [full $9.72 million MLE], [$3.8 million BAE]

Option 2: Trade Whiteside for a player on a multi-year contract

This scenario is floated most often, with players like Kevin Love and Blake Griffin being mentioned.

Pros: Starting-quality forward is acquired and will be retained for multiple years, turning the Blazers hypothetical cap space into a tangible asset without contract negotiation. Hood and Bazemore could be retained using Bird rights.

Cons: It’s impossible to do the math without knowing the salary of the incoming player, but the Blazers would be right at or over the luxury tax. They would also be essentially married to the new player who would, by definition of being tradeable for Whiteside, have a massive contract. The taxpayer MLE would be available, if they’re willing to use it.

Hypothetical roster:

Starters: Lillard, McCollum, Nurkic, [Whiteside trade], Hood

Bench: Simons, Little, Trent Jr., Bazemore, Labissiere on minimum deal, [$6 million taxpayer MLE]

Note that this assumes a package for the new high-salary player is Collins + 2020 first round pick + Whiteside. That is JUST a hypothetical to show what a move might look like. If you think a package like Little + 2020 pick + Whiteside will get a deal done then adjust the roster accordingly.

Option 3: Trade Whiteside for another expiring contract

The third option is to trade Whiteside for a player on an expiring contract.

Pros: This is actually my preferred scenario. It gives the Blazers maximum flexibility. If they decide their new acquisition isn’t working out, they can pivot to the cap space or MLE/BAE scenario outlined above.

If the new player does work out they’ve converted Whiteside’s contract into the Bird Rights of a good player, conveying all the possibilities of trading Whiteside for a player on a long-term deal.

Cons: The only con here is that Olshey would need to negotiate a new deal with the player on the expiring contract. The free agent market next season projects to be weak, so this may be complicated if another suitor has significant cap space. The Blazers renowned locker room culture might be a major factor.

Hypothetical roster: All of the rosters outlined above are possible.

Here’s another hypothetical that assumes Collins doesn’t need to be dangled for a player on an expiring deal:

Starters: Lillard, McCollum, Nurkic, Collins, [Whiteside trade]

Bench: Simons, Hood, Trent Jr., Bazemore, Labissiere on minimum deal, [$6 million taxpayer MLE]

What about Kent Bazemore’s expiring contract?

Why are we talking about Whiteside? Isn’t Bazemore also on an expiring deal?

Bazemore could be traded instead of Whiteside, but I prefer trading the latter. There’s just no scenario where Whiteside is in the Blazers long-term plans. If he plays well this season then he will likely want a starting role, something Portland can’t offer. If he plays poorly then he’s not necessarily a player you want to retain. Bazemore, on the other hand, is a solid role player who could probably be retained on a reasonable deal and fit a role on Portland’s bench.

If a team outright refuses to take back Whiteside in a trade, then Bazemore could obviously be floated instead, but that scenario probably costs the Blazers both Whiteside and Bazemore in the long-term. Whereas trading Whiteside gives the option to retain Bazemore.

EDIT: Salary implications

The Blazers will pay A LOT if they do trade Whiteside. Here’s a best-case scenario from a roster construction point of view as an example:

Worth it.

Who would you target?

IANAGM (I am not a GM) so I’m not going to speculate about which players to target. Besides, I’m over a thousand words so my editor will kill me if I write more. Let us know who you would like to acquire in the comments!