It's like the Antonio Brown list, which is worth a read.
Let's just start from after the World Series.
2006: Gets rid of Frank Thomas. Thomas finishes 4th in MVP voting in 2006.
After opening a hole in CF by trading Rowand for Thome, they trade top prospect Chris Young for Javy Vazquez.
Brian Anderson is bad.
Despite a monstrous offense powered by home runs in 2006, barely miss the playoffs.
2007: Thanks to Kenny gutting the farm system and marquee free agent signings like Darin Erstad, they get old and bad.
Kenny's pseudo-rebuild/retool is built around top prospects like Josh Fields, Jerry Owens and Danny Richar.
The first round picks are all "safe" guys.
Sox miss out on acquiring Miguel Cabrera because Jerry doesn't want to take on Dontrelle Willis' contract.
2008: They get to the playoffs but their MVP candidate breaks his hand cause he was angry and punched a bat.
KW Jr. drafted in the 6th round.
The Sox trade re-acquired Gio Gonzalez and Ryan Sweeney for Nick Swisher.
Dave Wilder scandal
Swisher is shipped out after one year because he's toxic as hell.
2009: Ozzie is getting on Ozzieball now. Rios is brought in to replace Dye. Thome is shipped to the Dodgers.
Beckham looks like the future at 3rd base, but the Sox decide they need Mark Teahen because even back then, they enjoyed trading with the Royals. Getz and Josh Fields are traded to the Royals. This creates a disastrous butterfly effect.
Sox pick Jared Mitchell ahead of Mike Trout cause Jerry hates high school players.
2010: Sox trade Daniel Hudson for Edwin Jackson. Hudson is still pitching.
Because of Teahen, Beckham becomes the second basemen. He later talks about how this kinda played with his head.
The rotating DH
Ozzie and his kids become a distraction.
2011: Adam Dunn
Ozzie negotiates with Marlins to leave mid-season
2012: Robin Ventura hired despite no managerial experience.
Jerry lets Buehrle leave for a reasonable contract
Trade Chris Devenski for Brett Myers
Trade Eduardo Escobar for Liriano
2014 and 2013 are just sad, but can be summed up with stuff like Jeff Keppinger and Adrien Nieto
2015: Sox go big!
Melky signing
Adam LaRoche
Trade Semien, Phegley, Bassitt and Ravelo for Samardzija and Ynoa
Sign Robertson but that was fine
2016: The death spiral begins
Sox trade Montas, Thompson and Micah Johnson for Todd Frazier
Fucking Drake LaRoche
Trade Tatis (and Erik Johnson) for an imploding James Shields
2017: Trade Sale, Eaton, and Q because they colossally fucked up everything.
2018: Lose a lot, draft Nick Madrigal.
Lucas Giolito goes outside the organization because the instruction he's getting sucks.
2019: Lose a lot, draft Vaughn to play first base.
Don't sign Machado when they were the only bidder because they tried to toy with him.
Don't even try for Bryce.
2020: Have a real shot at Wheeler. Miss.
"We have an All-Star catcher. Sign another."
Tbh I was fine with Yasmani, but still kinda dumb.
Eloy gets hurt cause they never taught him how to play defense. Play Vaughn in left field.
Rush Crochet to majors as a reliever. Botch his development.
Burger and Sheets seeks development outside the organization.
Omar Vizquel scandal #1 breaks.
2021: Hire TLR despite having their pick of the litter.
Miss out on Joc because of a small amount of dollars.
Omar Vizquel scandal #2 breaks, this one with organizational implications.
TLR's nonsense.
Leury extension.
Rename Loretta's Lounge for no reason.
Acquire Craig Kimbrel, use him wrong.
Squabble with Giolito in arbitration.
And I don't even need to start typing out the past two years. And I missed other moments from the past 18 because I was just going off Baseball Almanac and my memory, but there are organizational things like not spending wisely internationally, home grown players like Flowers and Semien becoming better defenders once leaving the Sox, trading international spending allotment etc.
Being a Sox fan is death by a thousand cuts and Jerry is very pennywise/pound foolish. There's a reality where they have a homegrown infield of Semien/Tatis/Anderson/Abreu for the past few years. Don't even need to spend a Madrigal pick!
Everything they do is so fucking stupid and self inflicted.