If you remember -- before the Raptors became a perennial playoff team -- in December 2013, the Raptors had just traded Rudy Gay to Sacramento and it appeared newly-hired general manager Masai Ujiri was set to tear down the roster and perhaps line up the team for a shot at the number one overall pick and Andrew Wiggins.
The next person on the block after the Gay trade was Kyle Lowry, who was headed to free agency and an expendable asset on a rebuilding team. The deal on the table would have netted the Raptors a future first rounder. As the story goes, Knicks owner James Dolan vetoed the trade, likely because he had just given multiple picks to Ujiri for Andrea Bargnani (the two also got together for the Carmelo Anthony trade back when Ujiri was general manger of the Nuggets).
The trajectory of the Raptors would have obviously changed had the deal gone through. Just how close was the deal to be completed? According to Kyle Lowry, who appeared on the latest episode of J.J. Redick's podcast -- which you can listen to here -- the deal was done. You can listen to it more in-depth, but Redick says he heard from another player who was with Lowry's agent Andy Miller at lunch that day that the deal was done. Lowry confirms that, saying he had already packed two duffle bags at his home in Toronto that afternoon, and was waiting for a call from Miller to take a flight to New York.
Lowry also said he would have wanted to sign a one-year deal with the Knicks that summer, and testing the market again (in what would have been last summer). A few hours later, he got a call from Miller who told him the deal was off, and the rest is history.
To this day, it's still quite a what-if to consider where the Raptors would be now if Dolan hadn't vetoed the trade back in 2013.