Biggest Sports Related Regrets (1 Viewer)

Dolphins choosing Culpepper over Brees.
 
How about us missing out on Troy Polamolu-1, Terrell Suggs-1, Dallas Clark-1, Osi Umenyiora-2, Mike Doss-2, and Eugene Wilson-2, Jason Witten-3, Lance Briggs-3, Asante Samuel-4, David Diehl-5 just to name a few, and drafting:
John Sullivan-1
Stinchcomb-2
Cie Grant-3
Montrae Holland-4
Melvin Williams-5
Karem Kelly-6
Talman Gardner-7

2003=worst draft with multiple picks
 
Biggest regrets? All Saints-related, right off the top of my head and in no particular order.... 1) Chargers go with Rivers over Brees 2)Chargers let Sproles go 3) Whole league whiffs on Pierre Thomas in the '07 draft 4) Haslett goes with Brooks over Blake 5) Finks lets Mel Gray escape in Plan B free agency
 
Mistakes I've been alive to see:

NFL - Dolphins choosing Culpepper over Brees
NBA - Portland drafting Oden over Durant

And the biggest regret of all time is Bowie over Jordan

Poor Portland
 
The Cowboys letting Sean Payton go
The Raiders drafting JaMarcus Russell.
The Chargers letting Brees go so Rivers could be the starting QB, only to see Brees win a championship with the Saints.
And moving the Raiders out of L.A.

From the NBA: Moving the SuperSonics to Oklahoma City
 
Horrible mistake?? The Redskins picked Champ Bailey, a perennial probowler with our first round pick ....and the next year they got Lavar Arrington with our 3rd spot pick. He was a beast until he got hurt.

Casserly took Ditka for a ride on that deal.

"After further review, the call is reversed." Totally forgot about Champ.
 
How about us missing out on Troy Polamolu-1, Terrell Suggs-1, Dallas Clark-1, Osi Umenyiora-2, Mike Doss-2, and Eugene Wilson-2, Jason Witten-3, Lance Briggs-3, Asante Samuel-4, David Diehl-5 just to name a few, and drafting:
John Sullivan-1
Stinchcomb-2
Cie Grant-3
Montrae Holland-4
Melvin Williams-5
Karem Kelly-6
Talman Gardner-7

2003=worst draft with multiple picks

We have ourselves a winner! Yup, this is the one for me too. We couldve had Troy Polamolu, instead we moved up to draft a bum. Oh what couldve been.
 
Three pages and nobody has mentioned the Bambino?

I'm fairly sure that the Red Sox sale of Babe Ruth is considered one of the most regrettable player transactions in sports history. If not the top of the list.
 
I agree that Portland not picking Jordan has to be the #1 sports regret. Here are a few regrets that I have lived through. Some Saints, some not..

George Rogers instead of Lawrence Taylor in the 1981 Draft.

Alex Molden instead of Eddie George, Marvin Harrison, Eric Moulds, or Ray Lewis in the 1996 draft. The George pick would have made sense since we hadn't had a 1,000 yard rusher since Hillard and wouldn't have one until Williams.

The Buffalo Sabres failing to re-sign Chris Drury and Danny Briere on July 1, 2007. The team was backed into a corner and forced into a huge Thomas Vanek contract by the Oilers. The team hasn't won a playoff round since and Briere has more points in the playoffs than every single Buffalo Sabres player combined.

Lonnie Smith getting deked by Greg Gagne and Chuck Knoblauch on Terry Pendelton's double in the 8th inning of game 7 of the 1991 World Series. Smith should have easily scored on the hit and run play called by Bobby Cox. I still can't believe how foolish Gagne and Knoblauch made Smith look.
 
As far as the Saints go.. Way back in 1993 or 1994 the Saints were poised to sign a little known back up quarterback off the Atlanta Falcons roster, Well his agen was asking for around 4 mil per year and Saints GM Bill Kuharich balked at the idea, saying "not many players are worth that, and he's not one of them"

That player was Brett Farve.
 

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