Well, I'll give ChatGPT a "B" on this assignment.  Nishioka at #1 on the list seems an obvious call.  David McCarty was perhaps the most disappointing Twins prospect in my memory.  So much was expected, and it just didn't work out at all.  Felton and Worely are deserving of spots, although I could also name a dozen other equally deserving pitchers (Ron Davis being the obvious omission).  Drew Butera... as a hitter, for sure, but I don't believe anyone expected him to hit much.

Teufel is a strange choice, as he was a fairly productive hitter for the mid 80's (and they got his playing dates wrong.  He left in 1985).  OPS+ of over 100.  My recollection is that the Twins were not enamored with his defense.

Ron Coomer... I remember him as being one of the better players of those late 90's Twins teams... which probably says a lot about how bad those teams were.  1.4 career WAR in over 3000 career at bats?  Perhaps a better definition would be mediocre, rather than struggling.  

I can't really argue that these players most definitely "struggled".  There are plenty of others over the years - especially in the pitching department.  I think it would be really interesting to find out which players' reputation with fans outshone their actual production on the field.  I can think of a few, like Willians Astudillio, Nicky Punto, and Denny Hocking, but I'm sure there are more. Nothing against those guys, they were who we had at that moment in time, but there was definitely some time on the struggle bus for each of them.

By the way, Ron Coomer was an All-Star in 1999. Yes, the rule than was that every team had to have one player picked, but still - Ron Coomer, American League All Star, 1999. 

Less a matter of most of those guys "struggling" and more a matter of most of them not being all that good at baseball.

How about a list of the top ten "snake bit" players or prospects in the Twins system? That would include guys that never quite made the bigs.

Am I the only one that notices the inclusion of Gene Glynn who never played a single game for any MLB team, much less the Twins?

One of these worst players hit .266 and one hit .274 so they would be stars on this weak hitting team. 

Of the guys who played over the last 30ish years, I think I'd only include Nishioka and Worley on the list, and I could be talked into McCarty.

I'd replace the other 4-5 with Sidney Ponson, Livan Hernandez, Byung Ho-Park, and while he was before my Twins watching days, the legendary Ron Davis.

It's hard for a player to be so bad that he literally becomes a Twins legend passed down thru the generations, whose song is as well known as those of Killebrew, Carew, Pucket, and Blylevin. Long live Ron Davis!