Insider Marc Stein has indicated the franchise is exploring scenarios to acquire the playmaker. This potential move serves two strategic goals. Primarily, the Knicks believe reuniting Holiday with his former Milwaukee co-star, Giannis Antetokounmpo, could eventually lure the "Greek Freak" to the Big Apple. Additionally, New York views Holiday as the perfect defensive complement to Jalen Brunson in the backcourt.
Holiday, acquired by Portland from Boston last offseason, remains highly productive despite being 35. He is currently averaging 15.3 points, 6.9 assists, 4.6 rebounds, and 1.3 steals. However, his contract presents a hurdle; he possesses two remaining years, featuring a $37.2 million player option for the 2027-28 season. Ultimately, trading for this championship-proven guard would signal New York's immediate ambition to compete while positioning themselves for future superstar acquisitions.