Carlos Palomino was considered a safe bet by for John H. Stracey when he was brought over to London, and Stracey's own team admitted as much after the fight. Huge error of judgement. Emmanuel Steward confessed to Greg Haugen afterwards that he'd never seen him fight or even properly heard of him when he picked him as a voluntary defence for Jimmy Paul. Not one of Emmanuel's better choices as it turned out.
Wilder fought Fury because he thought Fury was fat and straight off the couch. He also avoided AJ, well actually, they both di . Which makes them frauds. Although Fury is a PEDs cheating fraud on top. So yes, Wilder fighting Fury was cherrypicking gone wrong.
Jeff Fenech’s team picked Calvin Grove as his comeback fight from the Nelson loss because he was the type of light punching cute boxer that Jeff usually chewed up and spat out. They didn’t figure that Grove had a bit more pop than advertised or that Jeff’s chin and aura of invincibility were totally gone.
I've always figured that Betulio Gonzalez vs. Shoji Oguma was an instance of this. They had a ten-round fight in Japan, Oguma's first at world level, and Gonzalez won. Somehow this was followed by Oguma challenging for the title. I assume that Gonzalez's team arranged for a title bout, believing that they could get a pretty good Japanese payday while not having to worry about a tough fight (after all, Gonzalez knows first-hand what it's like to fight the guy). Instead Oguma took a surprise SD in a poor contest with a strange distribution of scores (Oguma by 4, Gonzalez by 4, Oguma by 7), and Gonzalez was visibly furious.
Clum, your mention of the Gonzalez-Oguma fights had me thinking of a similar one. Tony Zale, while champ, fought a journeyman named Steve Mamakos in a non-title 10 rounder and didn't appear to have much issues with him. Tony decked Steve twice and walked away with the decision. Lo and behold, like Gonzalez-Oguma, Tony then puts the title on the line against Mamakos. Seems pretty simple, right? But Mamakos floored Tony, gave him pure hell and was ahead on points before Tony stopped him in 14 rounds. Looks like he really took Mamakos for granted the second time around.
Tyson vs Douglas may be the ultimate one I always felt Gatti-Robinson 1 was cherry picking gone wrong, Robinson had fought on HBO before in an exciting bout vs Holiday so he had some recognition but also was recently stopped in a few rounds prior to this fight. Gatti was coming back from the Manfredy loss.
Buster Douglas was supposed to be a tune up fight for Mike Tyson before he took on Holyfield ( if memory serves me correct)
I've got a cherry pick that went bad and is never considered one,,, Roberto Duran's non title fight with Esteban DeJesus. After winning the title to keep Duran busy they had a bout at 140 with DeJesus? Seems strange that Arcel didn't know how good Esteban was, because he sure put his fighter in with a guy capable of winning the title not a tune up fight. He wasn't ready and it showed
That fight took place on Nov 17 1972 in Madison Square Garden, Esteban decked Roberto Duran in round 1 with a left hook, then went on to take it on points. In the title match in Panama City, Panama on March 16 1974, De Jesus again decked Duran with the same left hook. But Roberto got up infuriated, then went on to stop Esteban in round 11 to retain his title.