Maybe, maybe not

As Buck HC they would expect a championship or nothing else, and rightfully so when you have arguably the best basketball player in the world on your team. But, that’s a tough spot for a first time HC. It’s also an older team and although Giannis and Holiday seem like good guys, you never know how they will handle listening to a new, inexperienced, HC. Middleton might not be on the team next year and Quinn will probably have 2 years to get to the championship or they will reevaluate him as a HC. Giannis doesn’t have a big window to win again there and they will always be worried he might force his way out. I think it makes more sense for Month, but not necessarily Quinn.

Meanwhile Detroit is a young team with one of the best chances to get the first pick in the draft and a generational talent. If Quinn coaches there he will have a few years to learn as a HC while his young talent develops. He would not need to win a ton for a few years as the young players mature. But a team with Wembamyana, Cunningham, Ivey and even Wiseman could be very good in 3-4 years if they get close to their ceiling.

Even if Detroit gets Henderson or Miller, it still will be a very good young core and a good place for Quinn to build up an organization from the ground floor the way he wants it. Milwaukee, although a very strong team, is kind of set in what they are. There is not alot of trade pieces there to
Improve the team and you won’t find many starter caliber players dying to sign there as a free agent.