GIL CASTILLO
Fought Matt Hughes for the welterweight title @ UFC 40, 11/22/02

When it comes to unqualified title challengers, Gil Castillo getting a shot at Matt Hughes might be the biggest head-scratcher of the Zuffa era. Castillo first entered the Octagon as a 5-0 prospect, immediately fighting Dave Menne for the vacant middleweight title at UFC 33. Castillo lost in a 25-minute snoozer, and immediately dropped to 170 pounds. After just one victory over Chris Brennen at UFC 35, Castillo was given the green-light to fight for the welterweight belt. Your guess is as good as mine.

Hughes had already made successful title defenses against Hayato Sakurai and Carlos Newton, so Castillo was an easy meal by comparison. The Country Boy slammed Castillo to the mat immediately after the fight started, and spent the entire first round slugging him with strikes from the top. Near the end of the frame, a clash of heads opened a cut above Castillo’s left eye that led to the fight being stopped before the second round. Maybe the match should have been ruled a no-contest instead of a TKO win for Hughes. On the other hand, making Castillo face Hughes in a rematch would constitute cruel and unusual punishment.

JUSTIN EILERS
Fought Andrei Arlovski for the interim heavyweight title @ UFC 53, 6/4/05

The UFC was under no illusions that Justin Eilers deserved a shot at a title — even one of their relatively meaningless “interim” titles — especially since he had just come off of a first-round knockout loss to Paul Buentello. Unfortunately, Arlovski’s original opponent Ricco Rodriguez had to pull out of the fight due to problems with his training camp, and Buentello, who was already scheduled to fight Kevin Jordan at UFC 53, was apparently unwilling to fight Arlovski on short notice. Eilers was the best available warm body at the time, and God bless him, he tried his best. When the dust had settled, Eilers had broken both his hands and his right foot, sprained his left ankle, tore his right ACL, and broken his nose, en route to a first-round TKO loss.

THALES LEITES
Fought Anderson Silva for the middleweight title @ UFC 97, 4/18/09

Patrick Cote should have been enough proof that a five-fight win streak doesn’t necessarily make you qualified for a fight against Anderson Silva. Nevertheless, the UFC granted the next middleweight title shot to BJJ black belt Thales Leites, who had also racked up five consecutive victories, but managed to do it without scoring an impressive win against anybody relevant. Leites’s hit list included two UFC first-timers (Floyd Sword, Ryan Jensen), two gatekeepers (Pete Sell, Drew McFedries), and a split-decision against Nate Marquardt that Leites was gifted after Marquardt was docked two points for fouls. Was it any surprise that Anderson didn’t take him seriously? Leites butt-flopped his way to a unanimous decision loss against Silva, which was followed by a split-decison loss to Alessio Sakara, which was followed by his permanent exit from the UFC.

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