Every year there are a half dozen teams that can say, "we could have, maybe should have, won the title this year." That's the nature of the tournament.
In 2010, Kansas -- not Kentucky -- was the overall #1 seed with a line-up packed with EXPERIENCED NBA talent. Lost to Northern Iowa.
In 2011, Ohio State was clear and away the best team -- Kentucky beat them. Kansas had a 30 win team. Duke had a 30 win team. North Carolina was a very strong #2 seed. Kentucky beat them as well, as a #4 seed. Then the Cats' shooting went cold against a team with a super-hot guard (who had an excellent NBA career) and a team with better inside players. Oh for Enes Kanter...
In 2012, North Carolina fans still say they deserved the championship but Kendall Marshall got hurt. I say Bullshit, but it has as much validity as Kentucky fans saying the Cats should win it every time UK has a very good team.
In 2014, Florida under tested coach Billy Donovan beat Kentucky THREE TIMES. They lost in the Final Four. Arizona had a 30-win team and Wichita State was undefeated. Kentucky performed remarkably to make the final game -- in which WCS was out injured and Randle was clearly not 100 percent.
In 2015, there were four teams that were heads and shoulders above the others - Notre Dame, Wisconsin, Duke and Kentucky. The draw put Kentucky on a path to have to play all of the other three to win it. The worst possible match-up for Kentucky was Wisconsin. Yeah, the Cats still should have won, but it was a 4.5 point spread at the tip, not a 20 point spread. Teams lose games like that in the tournament every single year.
In 2017, Kentucky was put in the region with the team that was the clear favorite to win it all -UNC--Cheats. Despite one of the worst refereeing screw jobs in history Kentucky was still in position to take that game to OT - then came a lucky shot off a last second scramble. Tournament heart break. Not unique to Kentucky.
This year, Alabama, Houston, Purdue, Kansas, maybe a few others all could make some specious case that with better luck they should have won the title.
I'd say, taken as a whole, Kentucky probably should have won two or even three titles during Calipari's tenure. Injuries, bad refereeing, bad luck, and if you want to believe it bad coaching has so far limited that to one.
That's the nature of a lose and go home tournament. To say Kentucky should have won in 2010, 2011, 2012, 2014, 2015, 2017 is absurd. There were teams -- often multiple teams -- in every single one of those years except 2015 with a greater claim to having fallen short than Kentucky.