To Trade Or Not Trade For Jrue Holiday Is Now Brad Stevens' Million Dollar Question

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At the start of the week, I think most Celts fans were ready to enter another massive Celtics season with the roster as it stood. They'd made their moves, some big, some more around the margins, and I think most considered this new collection of talent good enough to win the NBA title. In fact, I'd go so far to say that's the expectation.

Then the Dame trade happened and suddenly with just a few days to go before the start of training camp, there's another potential move that every contender in the league is calling about. 

Trading for Jrue Holiday.

The question now becomes, should Brad do it? While I do think it's always important to take Celts trade rumors with a grain of salt, I also live by the rule that at the end of the day just wait for Adam Himmelsbach to tell us what Brad is actually doing. He's usually the one that puts water on trades/signings etc, so when he said this

That's all you need to hear to trust that this is something real. It's not an aggregation of a report of something a reporter "thinks" or anything like that. If Adam says it that means someone in the Celts front office told him.

OK, so now that the possibility is being explored, let's go back to the question. Should Brad do it?

As with everything, we do not operate in a vacuum, so the answer is a little more complicated. I do not think this is a "yes under any circumstances" type of trade. It's probably more in the "yes, but the deal has to make sense" type.

So what does that even mean?

The hard part of course is the money. Getting to Holiday's salary means around $33M in contracts needs to go out the door and the easy part of getting to that $33M is of course Brogdon's $22.5M. What makes this trade more of a debate is how you get the rest of that money.

While there is always the potential of massive 3 or 4 team trades, I think we have to be realistic here. At the end of the day, you're probably looking at two paths (barring some sort of Mike Zarren wizardry)

1. Pairing Brogdon with one of the bigs (Al or Rob)

2. Pairing Brogdon with essentially the entire bench who is eligible to be traded, plus a long shot Blake Griffin S&T.

Coming up with the money is one issue, but it's not the only issue. I don't really put much stock into the picks asking price, the Celts have more than enough to where they can overspend in that regard

Outside of putting together the salary to make this work, you also have to consider Holiday's pending extension in addition to the extension owed to Derrick White. I'm a firm believer that if Wyc comes down and says you can't extend both, then there's no reason to make this trade. You extend White. But if the only reservation is tax penalties and 2nd apron bullshit, I'm going to need Wyc to not be broke and just cut the check. He talked the talk, well now would be his chance to walk the walk. 

So let's assume Wyc gives the green light to pay whatever and extend both. Let's go back to the package ideas.

Looking at the roster, I think there's a legit concern that trading either one of Al or Rob in this type of deal would ultimately do more harm than good. We already have enough injury worries as it stands right now around Rob and Porzingis, so trading someone like Horford certainly doesn't really remove any of those concerns. What you gain in terms of perimeter defense, you certainly lose in terms of interior defense and in turn now need to rely even more on the health of Rob and KP with Kornet mixed in. That feels too risky.

If you say OK, trade Rob then instead. Considering his age/contract/production when he's on the floor, I'm not sure that makes all that much sense either. I think if it comes down to needing to include one of the bigs, Brad is better off passing. Remember, if this whole trade is to respond to the Dame/Giannis duo, getting rid of your best Giannis defender seems counterproductive, especially when you already have an All NBA defender to throw at Dame as it is. Rob can't guard Giannis, we don't know about KP, and I sure as shit know Kornet can't. I think to attack that duo defensively, you should have balance.

That of course means the other package path, which is something I think we all agree that Brad should be doing without hesitation. While it does hurt your depth considering Pritchard/Hauser/Kornet/Walsh etc would have to be involved, there are options out there to theoretically replace them 

You'd have to basically fill 3-4 roster spots if Brad goes this path, but you can figure that shit out. With Brogdon/PP/Hauser going out the door you definitely need to address your shooting considering the new guys (Brissett/Stevens) aren't exactly shooters which puts a lot of pressure on someone like Svi to basically be Hauser 2.0. Possible, but unknown. 

We should also be truthful when it comes to Jrue Holiday. There is no doubt he's a proven elite on ball defender when it comes to quicker/offensive minded guards (something Smart struggled with) who has championship experience, essentially zero drama or ego, is a good facilitator, and plays a style that fits. But it's also true he doesn't really guard up as well. He struggles with taller wings and bigs (whereas this is where Smart thrived). On the other end of the floor, he's been absolutely abysmal offensively in the last 3 postseason runs for the Bucks. I'm talking 47% TS%. For all the talk about how poor Marcus Smart's shooting is in the playoffs and how much people hated it, in reality, he's been a substantially better shooter over the last 3 postseasons by comparison regardless of the zone. 2pt FG, 3P%, it's pretty glaring

Now, let's also keep telling the truth. Jrue's role in this offense, behind Tatum/Brown/Porzingis, would not be the same as it was in MIL which is important to mention. At the same time, even in the Bucks title year when Middleton was healthy, Holiday's shooting was still abysmal. He shot 30% on catch & shoot 3PA as that 3rd option. For comparison sake, Smart has never dipped below 34.5% on catch & shoot 3PA and was 39% and 41% in two of the last three years and people still thought his shooting was a problem. I do not think this is something you can completely ignore considering the potential cost it would take to bring Holiday in. 

There's also the whole Brogdon angle to consider. What I mean by that is now that we all know Brad is calling and to do a trade like this you need Brogdon's money, it feels as though you now have to follow through. Immediately after coming out and saying he's ready and you talked everything over and he's good, only to then have him in more trade talks? I'm not sure you can keep that guy heading into camp at that point. 

So you add all this shit up and where do you net out? 

My thought is this. If you can keep both your bigs and Wyc has given approval that he's going to extend both Holiday and White, you put together whatever package it takes and overpay with picks if you need to. If it comes down to moving one of the bigs or Wyc says he's not extending both guards, I'm all set. 

Now, if you're one to believe random Twitter sources, it seems like Brad has picked a route