Folks, it looks like the Milwaukee Bucks are all in to win, and win now.
Following the recent max extension for recent swingman addition Jrue Holiday, the implications and reasoning behind such a large contract must be examined. Why pay all this money for a one-time All-Star who will be in his mid-30's by the time this max extension runs out. $135 million (up to $160 million) is no joke, and with three players on the books for over $100 million over the next few years, the Bucks just pushed all of their chips into the middle of the table to go all in on a title within four years.
For context, Holiday has already cost the Bucks a lot. It took Eric Bledsoe, George Hill, and five future draft picks (three first-rounders, two swap rights) to pry Holiday away from the New Orleans Pelicans. Since then, Holiday has been plenty solid: just this season, he has averaged 17 PPG and 5.4 APG through the 2020-21 season. Even more importantly, Holiday is currently second in the NBA in steals (1.8 per game), which signifies that he hasn't lost much, if any of the two-way prowess that made him a darling for the New Orleans Pelicans.
But if you are the Milwaukee Bucks, you have to ask yourself this question: if Giannis Antetokounmpo is the all-time great talent that he is, does the combo of Holiday and Khris Middleton equal a true number two option on a championship team?
Do you think that, with that trio, you can take down LeBron James and Anthony Davis, or Jamal Murray and Nikola Jokic? Even before you get to the NBA Finals, do you think you can get past Joel Embiid and Ben Simmons, or the Brooklyn Nets and their now-five-headed monster?
Because here's the thing: Giannis Antetokounmpo is amazing. Shaquille O'Neal even graced him as the next Superman of this generation of NBA big men. But he has a glaring flaw in his game: his jump shot. His playmaking could stand to improve as well.
In the regular season, both are fine. But a championship-caliber team, hell, a playoff-caliber team can figure out a way to take Giannis down in four games. Kawhi's Toronto Raptors did it, followed by Jimmy Butler and the Miami Heat a year later.
So to simplify: is the combo of Jrue Holiday and Khris Middleton good enough to cover for Giannis' weaknesses to an acceptable level over a seven-game series against a top-tier threat?
On paper, the answer is yes. Jrue Holiday and Khris Middleton are low-usage, low-maintenance, mid-level stars that are switchable for up to three positions each. Both can shoot, and at least Holiday can pick up the other team's player for extended time. If that holds true, then Jrue Holiday will have been worth every penny. NBA championships are worth $100 million per year.
If you're the Milwaukee Bucks, you just have to find out. To criticize this move would be to give an opinion too late in the game. If this is to be a mistake for the team, the real mistake for them would have been trading for him in the first place.
But, at the end of the day, this is Milwaukee, Wisconsin. Nothing against the city, but it isn't exactly a premier free-agent destination. If free agency was just playing alongside the best players or teams in the league, Giannis and the Bucks would have suitors out the door. But Kevin Durant, Kyrie Irving, hell, even Chris Paul couldn't be persuaded to go to Milwaukee.
The sad reality of the Milwaukee Bucks is that, outside of Giannis, the only way that they can get a verified star in their prime is through trading. That said, Holiday is probably going to be the best and biggest piece the Bucks will get outside of the homegrown duo of Antetokounmpo and Middleton.
Giannis almost left last season, by all accounts. More than anything, this deal proves that the Bucks are willing to overspend as much as Giannis wants to keep him happy and with them. It's a tough pill to swallow, but Milwaukee could do nothing but pinch their noses and take a gulp.
Time will tell if Holiday is the cure they're looking for.
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