Pirates reaping the rewards from a critical error the White Sox made in the MLB Draft

The list of reasons for the Chicago White Sox to regret selecting pitcher Hagen Smith with the No. 5 overall pick in last year's MLB Draft keeps growing.

First, it was slugger Jac Caglianone, who the Kansas City Royals took one pick later, tearing up the minors and leaving the Royals no choice but to call him up to the big leagues.

Caglianone was a good fit for Chicago. The White Sox needed to add a bat, especially a power hitter, more than they needed another left-handed hurler. It turns out the Sox could have also used a first baseman with Andrew Vaughn flaming out in 2025.

More regrets flooded in when Smith was shut down and sent back to the team's Spring Training facility to work on his mechanics after he experienced a dip in velocity and elbow soreness.

Smith has been on a pitch count since returning to game action in Double-A Birmingham and his 3.60 ERA is nothing spectacular. I worry if his arm will be able to handle a big league workload.

Now, maybe the biggest regret of them all, is Pittsburgh Pirates prospect Konnor Griffin being named MLB Pipeline's No. 1 prospect in all of baseball.

Konnor Griffin was a White Sox draft target

MLB.com's Jim Callis recently revealed that the White Sox were one of two teams legitimately interested in taking the prep shortstop in the top 10. He even recounted that the White Sox and the Pirates were the two teams not deterred by a potential issue with Griffin's swing.

Chicago ultimately passed, selecting Hagen Smith fifth overall, and the Pirates took Griffin at No. 9.

Instead of being bold and addressing a major need, the organization went the safe route, knowing they could develop left-handed pitchers. Pitching director Brian Bannister hinted after the draft that it was one of the reasons Smith was taken.

At the time, I felt that the team was drafting a replacement for Garrett Crochet, as it was unlikely they would pay him a massive extension. All signs pointed to the Sox trading Crochet in the offseason, which ultimately came to fruition.

Finances pretty much forced the organization to pass on a five-tool talent like Griffin because the organization had to draft a replacement for the homegrown pitcher that had developed into an ace.

Smith does have a high ceiling. He is considered the 31st overall prospect per MLB Pipeline and the third-best left-handed pitching prospect. Smith has a 3.60 ERA in 13 starts at Double-A Birmingham, along with 69 strikeouts over 45 innings this season.

But even if Smith develops into a quality big league starter, his value will pale in comparison to a superstar shortstop/outfielder like Griffin, whom I had been championing for the White Sox to draft. Griffin has the potential to be in the lineup every day as a cornerstone piece, and this is a franchise that needs more elite hitters.

Passing on Konnor Griffin could go down as an all-time gaffe by the White Sox.

Griffin has earned his top prospect status with a .927 OPS, 14 home runs, 50 stolen bases, and 37 extra-base hits in 90 games at Low-A and High-A. He is a true five-tool player who is only 19 years old and looks like he will only get better.

The White Sox may come out okay, even though they screwed this one up

Amateur scouting director Mike Shirley did at least circle back in the second round and take prep shortstop Caleb Bonemer after playing it safe with Smith in the first round.

Bonemer just cracked MLB Pipeline's top 100 rankings. He currently checks in at No. 99 and is showing a ton of promise in Low-A ball with an OPS over .800 and eight home runs.

The White Sox also just drafted prep shortstop Billy Carlson 10th overall in the 2025 MLB Draft. Scouts think Carlson had the best glove in the draft class, and if he can make a slight swing adjustment, he has the chance to be a really special player.

Griffin could end up bring nothing more than an average everyday player in the big leagues, much like Andrew Benintendi has become. Benintendi was once considered MLB Pipeline's top prospect back in 2017.

For the time being, Griffin is not the consensus top prospect in baseball. However, he is still considered a top-five prospect by FanGraphs.

Passing on a player with that much talent just does not look good for a White Sox organization that continues to be a master in bad optics, and it could stay that way if Griffin turns into a superstar in Pittsburgh.