Ainge full draft analysis based entirely on where a person would have been selected in a redraft. They are based on ranges and obviously the better the pick the smaller the range.
2003 - Banks (underperformed), Perkins (significantly overperformed), Hunter (slightly overperformed)
2004 - Jefferson (significantly overperformed), West (average - though mental rather than physical and Boston traded him before he imploded so Ainge used that one well), Allen (overperformed), Reed (overperformed for a 2nd rounder)
2005 - Green (underperformed especially for Boston), Gomes (significantly overperformed), Greene (overperformed)
2006 - traded a lottery pick for Sebastian Telfair (wasted asset), Rondo (significantly overperformed - gave up a future 1st which turned out to be 24 in 2007 so solid trade as well)
2007 - traded a lottery pick for Ray Allen (used asset well), Davis (significantly overperformed), Pruitt (overperformed)
2008 - Giddens (horrible), Erden (overperformed)
2009 - Hudson (overperformed)
2010 - Bradley (overperformed), Harangody (overperformed)
2011 - JJJ (horrible), Moore (significantly overperformed)
2012 - Sullinger (average - though like West had potential to be so much better), Melo (horrible), Joseph (average)
2013 - Olynyk (average)
2014 - Smart (underperformed), Young (underperformed)
2015 - Rozier (average), Hunter (underperformed)
2016 - Brown (slightly underperformed), Yabusele (horrible), Zizic (average), Jackson (average), Bentil (underperformed), Nader (significantly overperformed)
2019 - Tatum (overperformed - and the trade was even better), Ojeleye (significantly overperformed), Bird (average - then ended poorly), Allen (overperformed)
2018 - Williams (average - though could still go either way)
2019 - Langford, Williams, Edwards, Waters - All too early
So really Ainge hasn't done great in the 1st round in a long time (other than Tatum). He has however done well with his 2nd round picks, but doing well with those doesn't yield championship caliber players (except in uber rare situations) so I'd say he has been a fairly mediocre drafter on the whole, especially since Rondo (early on he had a lot more hits with Rondo, Jefferson, Perkins, Allen).