I wonder if playoff basketball exposes Jaylen's limitations (or just playing against the Heat). On defense, he's bad off-ball, so he can be schemed against, a bigger issue in long playoff series. On offense, there are fewer transition opportunities so his driving ability is limited. When he does drive, set defenses have a better chance of working on his bad handle, like the Heat when they collapsed on him. He seemed like he was working to get jumpers at the elbow, but a lot of those shots were really contested (he still makes contested shots due to his strength and lift, but they didn't strike me as reliable shots). So he can't initiate (because his passing isn't great) and can't get his own midrange shot reliably off, his drives are prone to turnover, and all that leaves is his 3-pt shot, which is variable.
Against PHI and ATL, his was hitting 3-PT shots at a higher rate and his FG% in general was higher. It all collapsed vs. Miami, so maybe they're just a horrible matchup for him. Then again, the turnovers were a problem throughout, and were a problem last year against the Heat and Warriors. Same with his unreliable FT shooting. Those strike me as issues the playoffs are going to highlight.
Regardless, if Tatum wants him back, and there's no way to get near equal value for him, you have to supermax him, right? It's not really about whether he deserves that much money or that much of the cap, it's that there isn't much else you can do without taking a huge step back, squandering some of Tatum's prime, and pissing him off. Unless Brad pulls off some wizardry like Hob is suggesting with HOU/BKN trades.