Could the Celtics leverage Damian Lillard's mandate to compete?

Damian Lillard will be 33 years old this summer. He knows he only has a few more years to be one of the star players to lead his team to a championship. Like Paul Pierce back in 2007 (though he was 3 years younger), Lillard would much prefer to compete with the only NBA team he's ever been a part of, but if that isn't possible, he's open to being traded.

The Celtics of course answered Pierce's prayers by dealing their #5 pick for Ray Allen, and their young star in Al Jefferson, plus two first round picks, and prospects Gerald Green, Sebastian Telfair, and Ryan Gomes for Kevin Garnett. The rest is history.

Could the Boston Celtics leverage a similar situation to retool on the fly and create a better team? A lot will depend on how much influence Lillard has with the Blazers.

Damian Lillard wants to win. He ideally wants to do it with the Portland Trail Blazers. Lillard knows that changing teams won't guarantee success, so he'd prefer the Blazers try and build a competitive team themselves.

“I want to have an opportunity to win in Portland," Lillard said. "We got an opportunity, asset-wise, to build a team that can compete. If we can’t do that...then it’s a separate conversation we would have to have."

There are three types of fans. One group gets super attached to their current players and never wants to trade anyone good. And of course you have to give something to get something, so you'd never want someone like this as your GM. They are the fans that were (or would have been if they are younger) against trading KG and Pierce in 2013, against trading Al Jefferson, and for giving Isaiah Thomas the brinks truck despite his future. They would have undoubtedly been against trading 7-time All-Star Ed Macauley (for a rookie named Bill Russell).

If you're in this first category above, you should probably stop reading now. The second group seems to always want to blow up the team and fire coaches. They have little patience and often just want to trade for or sign big names. They'd prefer the Celtics trade Jaylen Brown for an older star. They don't care much about the future. Just want to do something that might help the here and now.

Then you have the third group which I'd consider myself in and I try to hire writers who fit this mold. We are diehard Celtics fans, but root for the name on the front of the jerseys more-so than the ones on the back. We just want the Celtics to have a competitive team and are more objective about player values. If there is a trade that would make the Celtics better, we're for it. We know that tying up dumb money on a damaged goods player like Thomas would have set the team back. We disliked the inclusion of the last Nets pick (Could have selected Shai Gilgeous-Alexander) much more than a damaged Thomas in that Kyrie trade.

We realize that without trading Pierce and Garnett, there wouldn't have even been a Jayson Tatum and Jaylen Brown in Boston. We realize without a losing season in 2013-14 there would be no Marcus Smart on the Celtics. Or without a horrendous season in 2006-07 there would have been no #5 pick to trade for Ray Allen (and no Ray no KG).

We often get called "haters," but we're just as big Celtics fans as the Green Teamers that make up group 1. We know that an unknown future high draft pick is a better asset than a lot of current players on the roster. This 3rd group of fan is also who all general managers fall into.

If you're Brad Stevens this offseason, you're weighing super-maxing Jaylen Brown vs trading him. Not because you don't like Jaylen, but because it's your job to have the Celtics be contenders. If you give Jaylen $60 million a year that means you will have to gut your supporting cast in the coming years. If you trade him, you can keep the rest of the team, but you risk ending up with a worse team. It's your job to evaluate risks and take them if they are beneficial.

Group 1 will always choose the status quo "run it back" path. Well that path has a ton of risks too. Jaylen could get hurt and the Celtics may never win a title with the Jay's as the core.

The popular Jaylen trade idea that has been proposed around the internet and by NBA experts is Brown to the Blazers for Anfernee Simons and the #3 pick. What makes that trade appealing is the possibility that Scoot Henderson could be there for the taking at #3. Scoot has the potential to be a Ja Morant type without the guns. Simons is a great scorer and better passer than Jaylen, but doesn't have the size Brown has. Simons is younger too, but expecting him to become as good as Jaylen would be a tough stretch.

Scoot is the real prize. "But he's a rookie!" people will complain. Well so was Derrick Rose and Ja Morant and they became leaders of their teams quite quickly. Our very own Rajon Rondo won a title by his second season and was the Celtics best player by his fourth season (or potentially by the end of his 3rd).

If Lillard pushes hard enough for the Blazers to get his Jaylen Brown, the Celtics could demand Portland also kick in their impressive 2022 first round pick Shaedon Sharpe. Sharpe was drafted #7 and the Blazers have called him an "untouchable," but we've seen teams say things like that for posturing and reverse course many a times. The Suns were reluctant to include Mikal Bridges in the Kevin Durant trade, but once their new ownership took over, they basically gave the Nets everything that they wanted.

If the Blazers are committed to giving Lillard a second star, an All-NBA 2nd teamer at that, would they tell him "We almost got the deal done, but we chose to keep Sharpe instead." Lillard doesn't have the time to wait on a 20 year Sharpe. He wants an in his prime Jaylen Brown.

Now here is where the objective part has to kick in. Jaylen for Simons, Sharpe, and the #3 pick would be considered a trade way in the Celtics favor by fans of every team other than Boston's. So Stevens would have to kick in something else to pry the "untouchable" Sharpe away from Portland. The Blazers and their fans view Sharpe similar to how the Celtics and their fans viewed Jaylen after his rookie year.

Boston would also have too many guards if Simons and Scoot joined the team. I doubt former Oregon standout Payton Pritchard would be enough to level the trade, but he could be a piece. Cap wise, Brogdon would't work, but you could trade him elsewhere and use the asset you get in return as part of your package.

Swapping Jaylen (and let's say Pritchard and Brogdon) for Henderson, Simons, and Sharpe would allow you to retool and still compete with Jayson Tatum as the face of the franchise. He's the guy for the Celtics. You'd also pieces that fit better. Simons and/or Scoot handling the ball is a much better fit for Jayson than Jaylen handling it.

And if you're not sold on Henderson, Simons, or Sharpe, they all have trade value that you could swap them for someone you feel fits better. If you give Jaylen $60 million a year and he continues to be just the scorer he is then pretty soon his value will go way down to the point he's overpaid and a negative asset.

The more positive assets you have does not always create a winner, but when you have fewer positive assets and negative assets that never creates a winner. If you supermax Brown and Tatum which will take up 70 percent of the cap, don't expect to be able to retain other players you like like Smart, Derrick White, and Robert Williams. Don't expect to be able to add a worthy replacement for Al Horford in two years.

You end up more like the top heavy LeBron/AD Lakers, except unfortunately Boston doesn't attract players that will take less like Los Angeles does. And Tatum doesn't have the sway that LeBron has. If you love Jaylen Brown and want him to "be a Celtic forever" just know that that might mean not seeing a championship and an eventual trade of Brown regardless. This is why I was hoping Brown didn't qualify as a forward, so he didn't make All-NBA. Brown on a regular max contract is a fair deal. Brown on a supermax deal is an overpay and GM's will always try to move overpaid players.

If you're Group 1, stop rooting for the players you love to "get their bags." If you want a guy to remain on your favorite team long term you want them to either underpaid or on a fair contract. And it's also important to keep in mind that an underpaid NBA player is still a 1 percenter.

In order to win in the NBA you need some underpaid players. That's why players on their rookie contracts are NBA gold currency. Tatum and Brown on their rookie contracts allowed the Celtics to add guys like Horford, Hayward, Irving, and Kemba. Sure Boston chose or ended up with some bad fits, but it gave them a shot. Steph Curry on an underpaid contract allowed the Warriors to build, add, and keep their dynasty. If Curry had been on a max contract, let alone a supermax, the Warriors would have never been able to even entertain the thought of adding Kevin Durant.

The Celtics currently have no young players that could develop into stars, save for Robert Williams, but let's wait for him to get through even one season healthy before we go there. And if he becomes a star, then when his next contract comes up, Boston would have to either part with him, Tatum, or Brown.

This Jaylen Brown trade isn't for the sexy name you might want, but those trades are either not possible or also include Smart, Time Lord, and multiple FRP's as well. This trade is somewhat similar to the one I proposed prior to Tyrese Haliburton being traded to the Pacers. That was Brown and Smart for DeAaron Fox, Tyrese Haliburton, and the Kings first round pick. That pick ended up landing 4th and both Haliburton and Fox quickly became All-Stars.

At the time, most Celtics fans hated that deal, but only the biggest green teamers or Smart and Brown fan boys wouldn't want Haliburton, Fox, and a #4 pick now. Undoubtedly one of the Haliburton or Fox would have been moved in a subsequent deal. Now neither the Pacers or Kings would trade either of their lead guards for Jaylen even straight up.

So while Scoot, Simons, and Sharpe don't have the standing Jaylen has right now, that's the type of package Stevens would very likely jump at. Not that Brown, Smart and first round pick for Lillard idea going around the net. Not a trade for an older, oft-injured Bradley Beal. But a trade for a better fit and potential.

And then down the road if a star like Embiid, Booker, Giannis, or Doncic wants out, you actually have the assets to get them.