This is particularly interesting for the Philadelphia 76ers, as Holiday was a teammate of Sixers' general manager Elton Brand's from 2009-2012, while both were players for Philadelphia.
Holiday, 29, is one of the league's best all-around guards (19.4 PPG, 6.8 APG, 5.0 RBP, 1.8 SPG this season) and could be an intriguing compliment alongside Ben Simmons in the Sixers' backcourt. The bad news is, the Sixers do not have many trade assets not named Joel Embiid and Ben Simmons, whom almost certainly won't be traded.
I know some anti-Simmons fans will pine for the Sixers to trade him for Holiday straight up, but save your energy. That won't, and shouldn't, happen.
Holiday has a base salary of about $26 million and a cap hit of around $27 million for this year and next, with a player option for 2021-22. Matching the salaries will be tough for Philadelphia. Al Horford makes about the same amount over the next four seasons, but that doesn't totally make sense for either team in terms of on-court fit. As far as draft picks go, the Sixers do not have many valuable ones.
Maybe there's some sort of three-team deal Brand can figure out to bring Holiday to Philly, but in all honesty, it seems unlikely.