i kinda took it as Chuck desperately trying to get a ring when he was in HOU, not necessarily the numbers

He teamed up with Dream and Drexler to make a big three. And he got his eye dotted by Stockton
They were talking about the Warriors' time being up, so draymond said he doesnt wanna look like Chuck in HOU, doing last-ditch efforts and failing to get over the hump. For all the trash Barkley talks about "teaming up, bus riders/drivers, superteams", he did try the same thing but didn't find the success.
Also, I think it's lame that Barkley made an identity of hating on the Warriors. He's notorious for saying they couldnt win shooting jumpshots (even though that's not really the warriors system, just a lame generalization of it). He's been saying this "time is up" thing since the 2019 finals loss. Even when they went on to win in 2022, he kept picking the opposing team to win the series every round. shyt was lame. The TNT Inside the NBA youtube channel is scrubbed, but after the Warriors went up 3-0 against the Mavs in the 2022 conf finals, he was sticking to his schtick. It's tired. It's why he likes to crap on the Celtics, a team that also won a title "shooting jumpshots."
It seems more about him being happy the warriors arent contending anymore than anything else, so i'm not mad at Draymond calling him out for trying and failing at getting a ring in HOU