How much is too much in a Heat pursuit for Lillard?

Q: Speculative trade scenarios involving three or four teams to the contrary, the Heat are not giving up Tyler Herro, Kyle Lowry or Duncan Robinson, Caleb Martin, Nikola Jovic and Jaime Jaquez Jr. for Damian Lillard. I don’t recall Pat Riley ever making a lateral trade, much less a trade that makes the Heat worse, just for the sake of saying he obtained Lillard. – Morgan, New Orleans.

A: First, the Heat are not giving up all of that, nor would any trade partner dare expect all of that. The reasons you make trades are twofold. The first reason is to upgrade your core in a win-now setting. The other is to set up your future. With Jimmy Butler to turn 34 before the start of the coming season, the Heat are in that first, win-now category. So you start here: To win right now, is Damian Lillard an upgrade on Tyler Herro for the 2023-24 season? I believe most would agree. Then you look at having to shed other pieces and the impact on your core. With Kyle Lowry, you would have a replacement starter in Lillard, so you deal with that loss. The Heat have already shown they can win without Duncan Robinson, albeit a Max Strus replacement would be needed out of the developmental program. And it’s not as if Nikola Jovic is weeks, months or even a season away from being a rotation player for a championship contender. So part with those four plus a pick or two (or three) and you basically have done little to damage your core. Now, when you get to Caleb Martin or a ready-now Jaime Jaquez Jr., that is when you would take pause. So you can give up a lot. What you can’t give up is too much.

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Q: Minimum-level players to fill out the roster aren’t going to be perfect. They just need to be people who accept their roles. Common perception is Justise Winslow’s ship has sailed. However he would be returning as a much more mature person than the teenagers he was when he entered the NBA. By date of birth Winslow was born in 1996 like Haywood Highsmith, Gabe Vincent, Max Strus and younger than Caleb Martin and Duncan Robinson. Interestingly, by age Winslow would be close to re-signing a Strus or Vincent with a vastly different skill set. The caveat is injury history which is a big negative for Winslow. – Leonard, Cornelius, N.C.

A: I don’t think age or injuries are what most work against Justise Winslow. It is the lack of shooting displayed over an extended stretch. It is difficult to move forward with such a player in today’s NBA, even as Justise likely is there for the taking for a minimum contract in free agency.

Q: South Florida sports has never been better. Zach Thomas and Dwyane Wade are Hall of Famers. Great runs by our college and professional basketball teams in the tournaments and playoffs. Now Lionel Messi. This guy is incredible. Look what he has done to Inter Miami. Reminds me a little of when LeBron James was playing in Miami (27-game win streak) and when Shaquille O’Neal arrived. – Stuart, Miami.

A: I’m not sure if Messi isn’t on a higher plane than any of those. It’s sort of the South Florida equivalent of when Muhammad Ali worked out regularly at the 5th Street Gym in Miami Beach.

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