Entering Friday night, the Milwaukee Bucks hold sole possession of the fourth-seed in the Eastern Conference. The New York Knicks have a 3.5-game edge on the Doc Rivers-led Bucks while the defending champion Boston Celtics are up a manageable 5.5 games.

In order to cement themselves as a contender, the Bucks will need to upgrade their rotation before the rapidly approaching Feb. 6th trade deadline.

As of January 15, 96 percent of the league is eligible to be traded. Furthermore, a trade between two contending teams in the same conference is not common. However, the Celtics have slightly plateaued recently after Wednesday’s loss to the lowly Toronto Raptors.

A Bucks-Celtics deal could be mutually beneficial as the involved players would be introduced to a new environment. A swap could resemble the following proposal:

Bucks receive: Jrue Holiday, Xavier Tillman

Celtics receive: Khris Middleton, Delon Wright, 2031 first-round pick swap, 2031 second-round pick

Holiday would reunite with a Bucks team that he helped lead to the championship in 2021. Also, the Bucks have been repeatedly exposed by shifty point guards for a majority of the season–Knicks star Jalen Brunson dropped 44 points on the Bucks’ defense last Sunday.

34-year old Holiday would help deter that trend from frequently reoccurring. Holiday’s ball-handling and vision alongside Giannis Antetokounmpo and Damian Lillard would help unlock the relatively mediocre offensive unit. Additionally, Holiday would help hide Lillard’s poor defensive impact, especially in the playoffs. The savvy veteran is averaging 11.9 points, 4.3 rebounds, 3.9 assists, and 1.0 steals per game in 30.7 minutes.

Tillman could fill in as a relatively reliable backup to Brook Lopez. Although undersized, the 26-year old big man provides a strong rebounding presence, but doesn’t exactly offer much else. Unfortunately, he doesn’t fit the lob threat profile that Milwaukee’s front office has reportedly been seeking. Also, the involved draft capital is included due to the recently-benched Middleton’s lingering tendinitis and lack of availability this season.

Boston could benefit from moving the ball-handling Holiday as he is not nearly as impactful offensively playing off-ball. Through 34 games this season, Holiday is shooting just 33.7 percent from three on 5.2 attempts per game. In their offense, Holiday isn’t exactly necessary on a Celtics team with two ball-dominant superstars in Jayson Tatum and Jaylen Brown.

A 3-and-D wing like Middleton would fit better in the corners as the ball swings around the perimeter and would allow for higher usage from Tatum and Brown. Furthermore, this deal would allow for increased opportunity for veteran Derrick White and buzzer-beating maestro Payton Pritchard.

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