If that is his biggest regret, it wouldn't have been if Charlotte had accepted his trade offer to Winslow. Charlotte must certainly regret not taking this trade:
Chris Forsberg of ESPN.com reports the Celtics offered six selections, including four first-round picks, to the Charlotte Hornets in a deal for the No. 9 pick. The Hornets refused and selected Wisconsin Badgers star Frank Kaminsky, and then the Miami Heat took Winslow.
I still don’t understand why he was willing to throw so much to get Winslow, yet wasn’t willing to bring in Kawhi as a capstone to get us the title in 2018-2019.
Kawhi was recovering from injury and not really being forthcoming on his injury status and was saying long term, he would be playing in LA, so he would be a one year rental.
Winslow was a highly regarded prospect that fell in the draft that Ainge loved. GMs love their 19 year old prospects that they feel they can turn into stars and control for up to 8 or 9 years and will overpay for those guys.
Those are the reasons for that.
And it’s also why Toronto has as many titles as Boston in the last 35 years. Ujiri out-played Danny.
I bet Danny only wanted Winslow so bad because he knew he’s the guy Riley wanted at 10.
And who is more likely to win titles over the next decade because Danny didn't make that trade?
May still be Toronto.
I absolutely believe Boston wins the 2019 title that Toronto won had Boston traded Brown and Smart for Leonard (that was the rumored trade). That would have left the C's with a starting 5 of Irving, Hayward, Leonard, Tatum, Horford with Rozier, Morris, Baynes, Theis, and Semi on the bench (and still having Rob to develop). And if Boston wins that title, who knows what happens with Irving and Leonard. Perhaps they both really liked playing with each other and re-signed.
Anything is possible, but can you make the argument that Toronto is *more likely* to win a title than us over the next decade?
Next 4 Boston is clearly more likely, though I don't think all that probable that either wins a title. Over the next 10 though, I'd favor Toronto because of Barnes. He is in year 2, which means if they pay him the max, they will have his control the next 7-8 years. That just gives them a more firm and better chance than Boston. Now sure if Tatum and Brown re-sign on long term contracts, that would change, but with the way players move these days (after the rookie extension), I think there is at least a decent chance one of those, if not both, seek different pastures when their contracts are up. That is the belly of the beast these days. Players don't tend to leave before signing that first extension though, which is why I expect Toronto to have Barnes for well over 5 more years. Now obviously Barnes is young and raw, but he certainly has top 5 player talent. They have a relatively young and solid supporting cast as well and they did just win 48 games, so it isn't like they are a dredge. Boston should absolutely be better over the next couple, but 10 years is a long time and in that I'd bet on Barnes still being in Toronto and thereby giving them a better chance.
Also, if Boston did make that trade, who is to say Boston isn't in a better spot right now, even if Kawhi and Irving still left. They would have had Tatum on a rookie deal and space for 2 max contracts. Maybe, if Boston had cap room, Irving stays and brings Durant with him to replace Kawhi. There is no way to predict what might have happened if that trade had been made, but I absolutely believe that a Kawhi/Tatum/Irving trio would have beaten that Golden State team in 2019 and won the title.