No. 2 realistic Jrue Holiday trade: Boston Celtics
The Boston Celtics were on the doorstep of history in the Eastern Conference Finals, coming back from down 0-3, only to get ousted in Game 7 by the spunky Miami Heat. It was a disappointing finish for a disappointing team. A team built to win, but drowning in self-inflicted wounds.
Credit to Brad Stevens and the front office for going out and trying to get better. A midsummer trade for Kristaps Porzingis, involving former Boston heart and soul Marcus Smart, has the Celtics retooled for another deep run. There is, however, a question of depth at point guard. Derrick White and Malcolm Brogdon are both talented, but the Celtics could use a proper facilitator in the starting five.
Holiday is not without his offensive shortcomings — he's prone to some troubling cold spells as a shooter — but he's a tremendous table-setter, averaging 7.3 assists to 2.9 turnovers as the primary ball-handler for the No. 1 seed in the East last season. Holiday doesn't operate with the breathtaking flare of your traditional high-assist man, but he consistently makes the right read and plays a selfless, team-first brand of basketball.
The Celtics would benefit from Holiday's level-headedness in the halfcourt offense. Not to mention the defense, an area in sore need of reinforcements in lieu of Smart. Holiday is one of the few guards who can challenge Smart pound-for-pound. He's equally menacing at the point of attack (if a little less versatile) and would pair beautifully with Boston's unmatched defensive personnel.
Boston has to play catch-up after the Dame trade. The whole East does. This is the quickest and surest way to reaffirm Boston's title aspirations while potentially getting a leg-up on Milwaukee with the league's top Dame deterrent.
For Portland, Brogdon and Williams both carry trade value of their own. Williams could fit the timeline as a quality backup to Deandre Ayton (or potential experimental running mate), while two first-round picks next year is enough sweetener to get Portland on the phone.