Spending well over two decades with the Miami Heat as a coach and now as the team’s president, Pat Riley has experienced his fair share of shock and disappointment.

Under Riley, the Heat have dealt with some intense playoff battles with the New York Knicks in the ’90s, Alonzo Mourning‘s kidney illness, and Chris Bosh‘s blood clots. The franchise also lost an icon with Dwyane Wade signing with the Chicago Bulls last offseason. And the Heat also lost in the 2011 Finals to the Dallas Mavericks despite being the favorites with the Big 3 of LeBron James, Wade and Bosh. But for Riley all of these instances pale in comparison to James deciding to leave a perennial championship contending Heat team in 2014 for his hometown Cleveland Cavaliers.

In fact, James leaving the Heat in free agency is the biggest shock of Riley’s tenure with the Heat.

From The Vertical’s Harvey Araton:

“Since I came here, we’ve had the same owner, same president, two coaches, same support staff,” Riley said. “We’ve got a bunch of guys working for us who played for us. Players come and go, great players. When LeBron left, that was the most shocking thing to me – not to say he was right or wrong – and the most shocking thing to the franchise. But our culture is the same. You have your up years and your down years, but what can’t change is the way you do things.”

Riley choosing James’ departure instead of Wade’s departure is interesting. Yet James leaving Miami so he could make a homecoming to Cleveland, likely paved the way for Wade do the same by signing with the Bulls. But overall, Riley’s assessment of James leaving the Heat is probably right.

Since James left in 2014, the Heat have not been able to advance past the second round and didn’t even make the playoffs in 2015. This season, the Heat are making a late push for the eighth seed but very well could fail in their attempt of achieving a postseason berth.

Of course, if they do make the playoffs, the Heat could very likely face James and the Cavs in the first round, a series that would have a truly shocking outcome if Miami is able to beat Cleveland.