As the thread specified... who got the most head scratching title challenge and actually won the fight?
Pipino Cuevas - an unknown 18 year old kid who had just lost a 10 rounder to Andy 'The Hawk' Price. Price deserved the title shot but Angel Espada wanted Cuevas - obviously seeing an easy defense - but after the 2nd round, the rest was history.
At first I thought maybe Santana wasn't out of the realm of getting a title shot (even though his wins over Norris wer dubious), but after a quick look at his record, he had lost 4 in a row, then in '93 he beat Johnny Bizarro and Ronnie Gibbons, both decent enough fighters. But then I looked at the Ring's year end ratings and neithr Santana, Bizrro or Gibbons held any ratings at all. Moreover, Santan's title shot took place after exactly 1 year of inactivity. So I definitely agree, he was undeserving at this point.
Rob Brant against Ryota Murata. (I don't think any other org ranked Brant except the notorious WBA). Steve Cruz (late sub) against Barry McGuigan. Carlos Palomino against John H. Stracey Jeff Horn against Manny Pacquiao
I agree, Chucho Castillo is way out of line being on this list. He was the preeminent challenger all 3 times he went to the post. Also I disagree with Jimmy Braddock and Buster Douglas. Braddock did not hold a rating at the end of '34 but had to be just outside the top ten with his win over #4 ranked lt heavy John Henry Lewis. Then, in '35, he beat the #3 ranked Art Lasky. He deserved his title shot. Also, Buster Douglas was ranked #7 and Tony Tucker was ranked #8 at the end of '86. Both top ten ranked fighters, they deserved their title shots.
Montell Griffin against Roy Jones Jr. Don't get me wrong I think Montell was a good fighter. I just hate seeing a title change hands on a foul like that.
I'm late to the party, but these come to mind as fighters who have not yet been put forward: Billy Backus, Jimmy Goodrich, Freddie Cochrane, Lauro Salas.
I would agree with Cochrane. And Salas was really only a featherweight, but Backus was ranked in the top 3 when he fought Napoles, having beaten the #1 contender Manny Gonzalez a few months previously, so he was a deserving challenger. Also, Jimmy Goodrich had won 4 straight elimination bouts to fight for the vacant title, so again, was very deserving.
How about Kelvin Seabrooks? Had one recent quality win over Louis Curtis, and even he wasn't that highly regarded and just got kayoed by Yogi Buchanon 18 months before. Then Seabrooks gave us two great defenses and a fantastic FOTY with Orlando Canizales, so he earned his stripes afterwards.
Jersey Joe Walcott in the first Joe Louis fight. Okay, he didn't get the decision, but it seems people at the time thought it was an outrageous robbery he didn't.