It’s Draftmas Eve in Portland, and the city is buzzing. We aren’t quite sure if it’s nervous energy, positive energy, or toilet energy, where you fear the team you love is going to take everyone into an outhouse and tip the thing over with you inside. Let’s just call that the worst case.
What we know is that no matter what you tell yourself going into the draft to be reasonable, you know you’ll hope your team knocks it out of the bleeping park. That’s right. Here is a baseball analogy on what has become the most important evening for the NBA year.
This Draftmas Eve, Oregon Sports News presents a very special feature. Inspired by everyone’s favorite Christmas movie, Bryant Knox (BK) and Casey Mabbott (CM) will be participating in a choose your own adventure draft day version of the story.
What follows is not necessarily original, but it’s all in good fun.
It was the night before the draft, and one man was there to visit his family. He’s alone, tired, and the only chance anyone has got. The odds are against him, and that’s just the way he likes it. Welcome to Portland, pal!
After taking an Uber from PDX to downtown, Former Indiana Pacers president of basketball operations Joe Leland steps to the curb and jogs to the stadium. He’s in town visiting his family; his wife Christie works for the Trail Blazers and will be at Turtle Shell Square for the draft watch party. But this is not just a party for the team and their employees, the public has also been invited, with no tickets required. To gain entry, everyone is asked for the name of their favorite player drafted by the team, and it can’t be Bill Walton, Clyde Drexler, or Damian Lillard.
Joe goes through security and is asked who his favorite drafted player is. Joe smirks and says, “Cash considerations.” After a brief chuckle from the polite clerk, Joe says Moses Malone. The clerk looks skeptical, but a nearby employee whispers, “Merger draft,” in their ear, and they grant Joe access to the building.
Joe makes his way into the first concourse. Feeling foolish for not making plans, Joe is unsure what time or where he’s supposed to meet Christie, so he heads toward the elevators to go to her office.
Before calling for the elevator, Joe intends to use his iPhone to call his wife and realizes he is in a dead zone. But how can that be? There is always remarkable cell service at Turtle Shell Square.
Shortly after finding himself unable to contact anyone via a mobile device, Joe notices some unusual behavior from a group nearby. They are speaking with thick East Coast accents he can’t quite place, and the area around them just doesn’t smell right, like bad coffee.
Before Joe can decide if they are worth any more attention, the group rushes down to the court and gains the attention of the room with a series of air horn blasts. They take a microphone from the host welcoming those to the draft party and identify themselves as the Westchester Club, a small (very small) group of fanatics that passionately follow the Westchester Knicks, the G League affiliate of the New York Knicks. And their intentions are simple – they don’t want this evening to go as planned for the Portland Trail Blazers.
They announce to the group that cell phone communications have been disabled, and they immediately demand to speak to the highest-ranking front office executive. The current GM is escorted to them, where they are handed a tablet and told to follow orders to the letter.
Scenario One
Westchester Club’s leader tells the folks in attendance that he is Wilhelm Shoveller and will make this team trade their best player. As they follow only G League players, they are not sure who Portland’s best player is, so they ask the entertainment coordinator to put a graphic on the jumbotron and poll the crowd for their opinion on four different players while ordering the GM to deal that player to the Knicks for the 25th overall selection.
Joe doesn’t think any of these four players should be dealt, but he knows this Shoveller guy is serious. Your first task is to get Joe and the crowd to call out the player you think the team can afford to lose. Who will it be, and why?
- Anfernee Simons
- Jerami Grant
- Deandre Ayton
- Scoot Henderson
BK: In all my time pouring blood, sweat, and tears into the NBA, I’ve never seen a negotiator like Sir Wilhelm Shoveller. Not the recently crowned King Bradley Stevens of Boston; not even “Trader Bob” Whitsitt of Portland’s yesteryear.
This pill is a tough one to swallow but an easy one to choose. Anfernee Simons is the best player right now, and we can’t deny that. And if he’s dealt, it will be for the greater good of both Scoot Henderson and Shaedon Sharpe (not to mention the potential draft implications around Copper Flagg in 2025). Sorry, Ant. We have no choice.
CM: This team is a lot like Average Joe’s Gym in Dodgeball, we legit don’t know who our best player is yet, we’ve only played one season. I’m going to send Grant. Not because I think he’s the odd man out or the easiest to replace; it’s strictly because he’s the most talented player who probably doesn’t fit this team’s long-term goals. He just turned 30 and will be in his last years in the league by the time this team likely turns the corner. And he deserves to play for a playoff team now.
If you picked Simons or Ayton, skip to scenario two. If you picked Grant or Henderson, skip to scenario three.
Scenario Two
Shoveller doesn’t think the crowd or the acting GM know who the best player is. He’s not convinced his team’s parent team has been improved, and his actual team won’t get more players. He sends the GM into the 300-level concourse to get a beer and a dog (for $18!) and think about his choices.
Shoveller tells the assistant GM they need to trade their picks, but he doesn’t understand why the Bulls would need to be involved. He orders the assistant GM to contact the Bulls and give them the seventh pick in exchange for the 11th pick without explanation. Joe thinks Chicago would probably rather keep their pick and take Portland’s pick next year. He manages to sneak an iPad from one of the henchmen and heads to the 100-level concourse to contact the Bulls GM.
You make contact with the Bulls GM and let them know the scenario. They are willing to help but still want to make a deal since they only have one pick total. They offer their 11th pick in exchange for 14 and 25.
Do you accept the deal or offer to counter? Explain your reasoning.
BK: We accept! This draft class indeed lacks stars through the lottery, but there are enough rotation-worthy players who also fill needs, which is why I want No. 11. Imagine missing out on a Tristan da Silva all because you wanted to keep No. 25… Oof. Of course, you risk losing out on your shot at a gem every time you trade away a first-rounder. Are we willing to sacrifice that shot here?
For now…you bet. This Draftsmas Eve is all about swinging deals. And in this case, we’re swinging for the fences. Or ya know, maybe swinging more for a deep fly that awkwardly drops in deep right field to get us a double. (Oh great. This is another baseball analogy to describe this draft. That’s..not great, Bob!)
If you accepted the deal, skip to scenario four. If you countered the deal, skip to scenario three.
Scenario Three
The Bulls backed out of the deal, which kept the assistant GM in the hot seat, but it meant the Blazers still held three picks in the first round, which was the opposite of what Shoveller wanted. He demands the assistant GM contact the Wizards and offer their number 14 for Washington’s number 26 and number 51.
Joe thinks this deal is terrible, but he’s also a sucker for seeing second-round picks be
traded for cash considerations. He contacts the Wizards and asks them to make a more reasonable offer, but their GM won’t budge. Even with the 2nd overall pick, they want to get more picks. He offers to trade 14 for 26 and 51, and he will throw in a 2026 first-rounder.
Portland probably won’t have a first-round pick in 2026 if they have to send it to Chicago, so this new wrinkle appeals greatly to Joe. What do you do?
Agree to the trade or tell them to hang up? Explain your reasoning.
CM: This deal makes too much sense long term to pass on. You get a first-round pick in 2026, and all you have to lose is the lower of your first-round picks this year that you were probably going to spend on a project player or trade down anyway. You now have arguably more draft capital and could have a better/higher pick in 2026 than you would have now. It could mean you are still building your roster in two years, or it could mean getting a lottery pick when you don’t need it and adding to an already-loaded roster. Either way, your future is brighter with a potential lottery pick in two years than it is with the final lottery pick this year.
Skip to the final scenario.
Final Scenario
Not sure why trading their best player and moving down in the draft helps another team looking for young assets, Joe confronts Wilhelm in the suite level. Cowabunga mister falcon Joe says for no reason at all, and a confused Wilhelm demands to know his intentions. Joe says he loves this team and won’t see any more second-rate deals happen tonight without knowing the end game. Wilhelm laughs maniacally and tells Joe his plan has already worked. Portland has traded valuable assets while moving players Wilhelm likes closer to the picks the Knicks have acquired. Joe advances on Shoveller, who backs to the balcony of his suite where a terrified Christi has been hiding. Shoveller pulls Christi onto the ledge of the balcony, and holds up her left hand, showing her wedding ring to Joe.
“What are you going to do now that I have your wife Leland? It’s my time now!”
Christi whispers something inaudible, and Shoveller demands she repeat what she said.
“Joe knows what I said,” Christi says confidently.
“What did she say, Leland?!” Wilhelm shouts desperately.
“Dame Time, Mister Falcon,” Joe says, shoving Wilhelm while taking Christi’s hand in his own.
Shoveller tries to grab Christi’s wrist but fumbles with her Dame Time watch. He falls backward into the crowd below and is promptly escorted out by security along with the rest of the Westchester cronies.
Less than 24 hours before the draft, Joe was asked to stand in as GM on draft night. How are you planning to use your assets based on how you navigated the scenarios?
CM: We lost Grant, picked up #25, lost #14, but added a first-rounder in 2026 and a second-round pick this year. Not all bad. I think we need to make sure the pick at #7 is a big move, not just a roster filler. If options to move up are there and a team will listen to a trade offer for #7 and #25, you need to get one of the best defenders at #7 and hope one of your current players develops into an amazing scorer. If you can’t get a blue chip player at #7, I think you try to trade up from #25, maybe even package Ant in another deal. If a deal isn’t there without having to give up too many assets, stay at #25 and see if a guy like Daron Holmes would be a good long-term replacement for Grant, or you could look at Johnny Furphy and go with a long-wing. Furphy could be another Jake Layman, or he could be much better. We’ll have to see where he ends up and how he adjusts to the pro game, but I’d be willing to take him with a late swing in the first round. No matter who you take at 25, you’re not getting Grant’s production, so thanks for nothing, Shoveller!
BK: Having turned Anfernee Simons into No. 25 and then Nos. 14 and 25 for No. 11, we’re ready to keep dealing. Because we still have one of the best trade chips in the league at the moment in our war chest—Jerami Grant.
Casey traded Grant up front in his version of this choose-your-own-adventure draft. But I played the long game, knowing that a team like the Houston Rockets sitting at No. 3 would LOVE a Grant to further expedite their return to contention.
If the Rockets are willing to deal No. 3 for Grant and No. 14, I’m doing it in a heartbeat. And if they’re stuck on holding out for Grant and No. 7…I’m probably doing that, too. (Don’t tell Houston!)
There’s only one name, by the way, I’m trading up for: Donovan Clingan. He’s earning looks at No. 1, but he’s more likely to slip past Nos. 1 and 2, and that’s where the real discussion will begin.
If I’m Portland and have THESE assets ready to flip, I won’t balk. (Oh great, another baseball reference. Oh well—this one really is a home run!)
