Ranking the Milwaukee Bucks' offseason retoolings post-championship

After the Milwaukee Bucks hoisted the Larry O'Brien Trophy in 2021, many thought that they were in a position to earn a few more in the years that followed.

For one reason or another, they haven't, although it hasn't been for a lack of trying. General manager Jon Horst has consistently been working the phones over the past several offseasons, making the moves he believed gave this team the best shot to win it all. Some have been good, some have been bad and some have been somewhere right in the middle. No one can question the effort.

With that said, let us look at Milwaukee's major moves over the past several offseasons since winning it all and rank them by year.

No. 4 - 2021 offseason

Fresh off the championship, the Milwaukee Bucks needed Jon Horst to adequately stack the deck to help this team defend its title the following year. What followed was certainly a mixed result, with the former Executive of the Year making two strong moves and then a handful of them that looked good on paper but never panned out to Milwaukee's liking.

The good: Re-signing Bobby Portis, trading for Grayson Allen

After helping Milwaukee secure the title, Bobby Portis was destined to opt out of his deal, and many thought he'd depart. However, taking a sizeable discount, he returned to the Bucks on a two-year deal worth just under $9 million. It was an excellent move to help retain a key cog in the second unit on an incredibly team-friendly deal.

With the injured Donte DiVincenzo set to miss time, the Bucks made a trade for Grayson Allen to add shooting guard depth, giving up Sam Merrill, who scarcely played in his rookie season, and a pair of second-round picks. Allen went on to play some of the best basketball of his career in Milwaukee as he started for a good chunk of his tenure.

The bad/mixed: Signing Rodney Hood, signing Semi Ojeleye, signing George Hill, letting P.J. Tucker walk, drafting Sandro Mamukelashvili, drafting Georgios Kalaitzakis

Outside of those two moves, everything else was a swing and a miss for the Milwaukee Bucks. While both were signed on team-friendly deals, Rodney Hood and Semi Ojeleye never found their footing and didn't even make it to the trade deadline. Milwaukee used a draft pick on Kalaitzakis but later waived him. Mamukelashvili showed potential but never panned out, eventually being cut.

The George Hill signing looked like an easy base hit for Milwaukee. With their backcourt point guard rotation all over the place during the title run, the Bucks brought in a familiar face to guide the bench brigade. However, Hill was not the same player he was during his first stint in Milwaukee, having taken several steps back, eventually being used as a trade chip.

Yet, even with all of those moves, the worst was letting P.J. Tucker walk after he played such a crucial role in them winning the title. For years, they have been searching for a player who can fill his shoes - let's hope Taurean Prince can do so this year - when they could have just given him his money. The lack of a reliable wing defender has come back to hurt this team again and again.