Milwaukee Bucks: Re-signing Khris Middleton to a 3-year, $93M contract extension
Here is the caveat: The Milwaukee Bucks had a great offseason, and this pick was tough. Sometimes the most regrettable move of the offseason is one that a team still needs to make. I ultimately went with this because Khris Middleton is another year older, another bit slower, another bit less efficient and you're giving him a long-term deal over $30 million per season at 32 years old.
For this pick, there's general concern over injuries and showing evidence of declining play, which isn't uncommon for early-thirty-year-old wings/forwards. If the Bucks could return any item they received this year, this would be the one.
Minnesota Timberwolves: Re-signing Jaden McDaniels to a 5-year, $136M contract extension
Another team that requires an explanation. The Minnesota Timberwolves are the best team in the Western Conference. They also had an awesome offseason. In this case, we have to nit-pick and nit-picking vet minimum moves or on-the-margin moves for the best team in the West ain't cutting it.
By default, we have to return giving Jalen McDaniels a 5-year, $136M contract. He's young enough and has the potential to make this contract sing. However, paying over $30M a season for five years for a guy who hasn't averaged over 13 points per game in his NBA career is an interesting look. The NBA does like its defensive-minded players, but they LOVE its offensive-minded players.