Manny Pacquiao
-Barrera
-JMM (who a lot of people didn't want to fight)
-Morales
-Morales II (after losing in a war, he fought him again)
-JMM II (after many people thought Marquez won, Pacuqiao took a risk and fought him again)
-ODLH (considered a horrible cherry pick at the time since DLH had gotten titles at MW and Pacquiao only had 1 fight at LW)
Miguel Cotto (even with the CW it was considered a big risk)
Margarito(even after a lose Margarito had a huge size advantage)
Bradley (Young prime undefeated boxer with good technical abilities)
Marquez IV (the 3rd fight was a cherry pick but the 4th wasn't even with a size advantage facing a guy that had arguably beat him 2-3 times was a risk)
Pacquiao =
10
Floyd Mayweather
-Hernandez (Floyd's age and first title fight)
-Corrales
-Castillo II (After arguably losing to Castillo he rematched him and beat him convincingly)
-ODLH (moving up in weight, not that big of a risk)
Floyd =
4
that's pretty much it. Only Trout, Martinez or Canelo fights would be risks.
Guerrero wouldn't. Maybe that speaks of Mayweather's skills and greatness or his great cherry picking skills + hype. Like trying to make a shot Cotto seem 2nd prime'd and undefeated, calling Ortiz the quitter a "Young hungry Lion"etc