New NBA TV Analyst Tom Penn Talks Trades, Free Agency, And The Lakers’ Tough Choice

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After eight years with ESPN as a cap expert and front office insider, former Blazers vice president of basketball operations Tom Penn is moving to Turner and NBA TV.

Penn will bring his cap knowledge to the Turner campus, joining former Cavs GM David Griffin as former NBA executives to come on board at NBA TV in the last two years. We spoke with Penn on Monday about his new role, thoughts on the Bulls situation, teams to watch for on the trade market leading up to the deadline, the Lakers deciding whether to make a move via trade or wait for free agency, and how teams learned better spending habits from the summer of 2016.

What excites you about joining NBA TV in your new role and what you’ll be doing there, joining a roster with a number of former players, executives, and coaches at NBA TV who have different perspectives from their time in the league?

Well they offer best in class coverage and entertainment, frankly, around basketball and with my long run in the NBA, it’s been fun to watch NBA TV evolve into what it’s become, continue to see the dominance of TNT and Turner in general and I’m just really excited to join the family.

I think that’s what the viewers like, is the different experiences that result in varying opinions. My history was as a salary cap expert and then as an overall executive, so I particularly like talking about the business of basketball on the court and off the court and how it relates to the overall enterprise. Because that’s really what all these transactions are about. Half the time it’s about the talent. Half the time it’s about the money, and it’s rarely every about one or the other. So, it’s just fun to pick those kinds of things apart and talk about them.

The inescapable storyline right now is everything going on with the Bulls and the apparent power struggle between the players and new coach Jim Boylen. As an executive, have you ever seen anything like this in how it’s playing out so publicly, and how do the Bulls move forward?

Yeah this one’s hot at the moment. Any time you’re trying to change culture, direction, you’re in a state of flux as they’re in right now, the drama plays out it seems more and more publicly. What’s different now is just how it’s so immediately and freely out there. Many times by virtue of the direct channels of player communication direct to the masses. They’ll get through it. It’s all part of the process and they’ll be stronger because of it, but I don’t think its anywhere near over.

We’ve got a couple months before we get to the trade deadline, but when you look at how competitive the West is with 13 or 14 teams that think they have a playoff chance, do you expect it to be a fairly active trade deadline as teams jockey to make their rosters better and make playoff pushes?

I do. The more that are in striking distance, the better. The more that everybody feels like they have a chance, the better. The fact that LeBron’s gone from the East makes it wide open at the top. And the fact that the Warriors haven’t stomped everybody and left this thing open makes it really intriguing in both conferences. What I like is that we’re seeing teams not wait for the trade deadline.

I’ve always thought it was stupid to wait that long. If you look at what Philly did with the Jimmy Butler trade, it’s one of those that really has paid off well for both teams and both teams are responding and playing better. So often we wait until the middle of February to do these things and it’s just too late. So, the deadline creates urgency, creates deals. I’ve always thought it’d be great to have a preliminary deadline and a later deadline just to force more deals before Christmas.

We saw that last year with the Blake Griffin trade as well, so maybe teams are figuring that out. Do you see any teams specifically that will be more aggressive as buyers at the deadline?

I think a lot of teams can be aggressive. The most intriguing team to me is the Los Angeles Lakers with the deals they maybe don’t do. The great question with their championship build is what’s the next big piece to go with LeBron. They, I expect, will want to preserve and protect all flexibility for this summer to get a mass free agent without having to give anything up. Do they resist the temptation to do a deal right now to make them better right now? With the West as wide open as it is, I think they’re the biggest beneficiaries of that, because they’re up there in that top four conversation as is. So, that’s a really intriguing story through the trade deadline.

We talk about deadlines and December 15 is the first major deadline when players signed this offseason, like Trevor Ariza, can be dealt. The Lakers are reportedly involved in talks to try and land him and he’s the biggest name of those veterans that signed this offseason, but what other vets on struggling teams do you think could be on the move to contenders?

I think it’s all of those guys and all of those teams. Any veteran on a team that’s struggling. The difference here is there are less teams out of it. With only Phoenix stumbling out of the blocks [in the West], you’re going to have to wait and see how the rest of this shakes out, but that’s really unusual to see so many teams still in contention this far into the season. Usually the writing’s on the wall and there’s a clear separation. So, these have been some impactful moves already. Korver and George Hill, we’ll see what happens there, but Tyson Chandler going to the Lakers has dramatically changed their defensive statistics immediately. So, I think you’ll see more of these and then a flurry of them after the deadline (on the buyout market).

You mentioned earlier the Lakers wanting to keep flexibility for the summer, but there is a finite number of stars that will be available. There’s a real chance Butler stays in Philly and Kawhi stays in Toronto, and what happens if they don’t get those guys and KD goes elsewhere as well? What should they do if they strike out on the upper echelon of free agents and have $50 million to spend?

I can’t answer that because I have no idea how that all shakes out. There’s so much. You feel like Kawhi’s going to stay or Jimmy Butler’s going to stay because they’ve had a few good weeks, right. Any of these situations can go a little haywire, and we just might not know. I would bet on the Lakers not striking out. When you have Magic Johnson eyeball to eyeball with any free agent in the world, including LeBron James, it makes a difference. I think they have that, plus the story of what looks to be a successful campaign this season. They’re going to have a lot of momentum, and they’ve still got L.A. as a backdrop. They’re going to have a lot of momentum to ring the bell again. The qualitative question for them is can they beat it via a trade. Can they figure out a way to do a trade to get a path towards something that they’re guaranteed to have.

There are a lot of teams that have the ability this summer to create a lot of cap space this offseason if they want, and it’s really the first time we’ve had that since the summer of 2016 when there was the cap spike and a bunch of contracts that raised eyebrows and are still having effects on teams’ abilities to make moves this year. What do you think teams have learned from that summer going into this year where we have a lot of teams with space about how to spend and how to spend wisely if they don’t get those top guys?

Well we see a commitment to shorter term deals. Bigger money, shorter term. 2016 was different because we knew all that cap room was going to be there and we knew for a fact people had to go spend 90 percent of it. Here, in this case, I’m not so sure how much of that cap space will materialize because a lot of these guys are going to stay. So, it’s more like a normal year, just with a lot of free agents because we’ve gone through the cycle of those three year deals and guys signing up on one year deals. There’s going to be a lot of talent on the market, but I think you’re going to see the usual amount of retention of your own guys. Cause usually, if you lose a player like that you can’t replace.

If Charlotte loses Kemba Walker, it’s not like they can just go replace. You have to get a player of that stature ready to come in that same window of time. So the pressure is on just maintaining what you’ve got and sorting it out later.