I just looked at every NBA draft since 1947. There have been 13 times that two players from the same college were drafted in the Top 5 ...
1969 - UCLA (National Champion) - Kareem, Lucius Allen
1979 - Michigan State (National Champion) - Magic, Greg Kelser
1984 - UNC (Sweet 16) - Jordan, Sam Perkins
1995 - UNC - (Elite 8) Jerry Stackhouse, Rasheed Wallace
1998 - UNC - (Final 4) Antwan Jamison, Vince Carter
2002 - Duke - (Sweet 16) Jay Williams, Mike Dunleavy
2004 - UConn (National Champion) - Emeka Okafor, Ben Gordon
2005 - UNC (National Champion) - Marvin Williams, Ray Felton
2008 - UCLA (Final 4) - Russell Westbrook, Kevin Love
2010 - Kentucky (Elite 8) - John Wall, Demarcus Cousins
2012 - Kentucky (National Champion) - Anthony Davis, Michael Kidd-Gilchrist
2014 - Kansas (Round of 32) - Andrew Wiggins, Joel Embid
2019 - Duke (Elite 8) - Zion Willamson, RJ Barrett
So, to recap ... 13 times it has happened and every team had made the tournament, five won national championships, two more made the Final 4, three more made the Elite 8, two were knocked out in the Sweet 16 (both of whom were #1 in the country going into the tournament), and one was knocked out in the Round of 32 (they were #10 in the country going into the tournament).
If Bailey gets drafted in the Top 5, we are in some seriously rare (and embarrassing) air.