Matthew Dellavedova’s path into the NBA was never built around certainty. It was built around the possibility that, at some unpredictable moment, a coach might finally look down the bench and call his name.
For Dellavedova, that moment came during an otherwise forgettable regular-season night in Washington, and he believes the lesson from it applies to every fringe player trying to earn a permanent place in the league.
“It’s hard to make a team as an undrafted guy. And then to break into a rotation is even harder. You never know when your chance is going to come.”
Dellavedova entered the NBA undrafted in 2013 before earning a roster spot with the Cleveland Cavaliers. As he remembers it, the opportunity that changed his standing inside the team did not arrive in some carefully prepared showcase. It came in the middle of a game in which Cleveland had fallen well behind and head coach Mike Brown was searching for energy.
“Mine was a sleepy Tuesday night in Washington. The starters were BSing. Down 20-something in the second quarter. Coach Mike Brown throws me in. We make a little run. Third quarter starters come out BSing again.”
What made the opportunity even more demanding was that Dellavedova had already put himself through substantial work earlier in the day. By the time he was asked to play extended minutes, he was not physically fresh. He had already conditioned and trained before the game, but he understood that fatigue could not become an excuse once the rotation door opened.
“Mind you… I’d already done conditioning three hours before. I’d already had a hard workout with Phil Handy and Mike Gerrity. So I’m already cooked. But the adrenaline’s flowing. They throw me back in. I play the whole rest of the game. The game goes to OT. We end up winning. From then on, I’m in the rotation.”
That experience became a defining example of how Dellavedova approached the uncertainty of being an undrafted player.
“You have to be ready when your opportunity comes. And you have to be a little crazy. You have to prepare like a psycho so that when your opportunity comes, you’re ready to win.”
For established stars, an uneven possession or slow start can be absorbed over the course of a long season. Players at the end of the bench often do not have that luxury. A single stretch of minutes can influence whether a coach trusts them again, and Dellavedova understood that his opportunity could appear without warning.
“It could be the second or third quarter of a crappy game on a Tuesday night. The coach looks all the way down the end and says get in. So I would be running back and forth during timeouts… Just staying warm.”
Dellavedova’s point was not simply about conditioning. It was about treating an uncertain opportunity as though it were guaranteed to arrive, even when there was no evidence that it would.
“Because I can’t go out there and have a couple possessions to warm up. I need to be ready. You get one shot… If you make that shot, then you go back in.”
Matthew Dellavedova says you have to prepare like a psycho for an opportunity that you never know when it’s coming
“It’s hard to make a team as an undrafted guy. And then to break into a rotation is even harder. You never know when your chance is going to come.”
“Mine was a… pic.twitter.com/mLaUQ7FhuK
— Josh Chambers (@JoshChambers) August 24, 2026
That mentality ultimately became inseparable from Dellavedova’s NBA identity. He built a long professional career not through draft status or overwhelming physical gifts, but through preparation, defensive effort and an ability to make himself useful whenever minutes became available.
