Ditto on Panda. Also, let's not forget Rusney Castillo, paid $72.5M to not play for the team at all. Well, "not play" may be a slight exaggeration, but a career WAR of 1.6 is pretty sad considering the cost.
Panda edges out Hanley in the “Obviously awful contract at the time” competition.
Carl Crawford could have reasonably continued to hit around .300 with some pop, good defense, and a ton of triples and stolen bases.
Hanley Ramirez could have reasonably continued to be a great hitter while being a passable defender.
Pablo Sandoval could have reasonably continued to be an above average third baseman while being a fan favorite, despite his size.
Panda was the absolute worst. I don’t know how that happened - he was being booted off his own team for his uncontrollable eating, and he refused to accept a weight clause in his contract. He couldn’t play or hit, and his poor belt. So of course the Red Sox do what no other team would do and inexplicably sign him to a huge contract with no strings attached (unless we’re talking about string cheese). If I can see something is a blatantly bad deal a mile away, then it’s a really bad deal.
This is after they ran their homegrown ace out of town with an insulting offer of 50% of his value. Luccino then did a media tour talking about how 70 million is “a lot of money” and that no pitcher over 29 is worth a decent contract. We then proceeded to watch John Lester pitch as an ace for the Cubs who won the series not long after. I still hate Larry Luccino.
*Baseball stuff aside, I hate his insistence on the fake pronunciation for his last name, so it will be less “Italian“ sounding I always suspected.
Hanley was bad and also totally preventable. He was known to be a flake and kind of a con artist who would say anything too get what he wanted. And his options were limited, so I don’t know why Cherington gave him the big contract.
And then there’s Rusney. They got outbid on the player wanted, so they threw all their money at the next one. 150 million (half went to Castro) without even knowing if he could play in the big leagues.
So I think Panda, Hanley, and Rusney were the worst, with John Lester being a bad decision in reverse - a gift that was thrown away.