Add Vaughn to list of White Sox regrettable draft picks

First of all, a reminder there are success stories in White Sox draft history.

They went three consecutive years picking Jack McDowell, Robin Ventura and Frank Thomas in the first round, from 1987-89. They drafted and developed three of the current best pitchers in baseball, Chris Sale, Carlos Rodon and Garrett Crochet.

But with first baseman Andrew Vaughn off to Milwaukee in a trade, those 2018-19 drafts will sting for a while.

The Sox took Vaughn with the No. 3 overall pick in 2019, after selecting second baseman Nick Madrigal No. 4 in 2018. All they have to show for those two players is right-hander Aaron Civale, a career 4.06 ERA pitcher who reportedly wasn't receptive to joining the Brewers bullpen.

So where do Vaughn and Madrigal rank among the White Sox' worst all-time draft picks?

Keep in mind, most mock drafts at the time had Vaughn as the clear No. 3 option behind Adley Rutschman and Bobby Witt Jr. It's not like the Sox scouting department went rogue and did something most teams wouldn't have. As a sophomore at Cal Berkeley, Vaughn hit .402 with 23 home runs. As a junior, it was .374 with 15 home runs.

But this line from the cbssports.com mock draft stands out: “The righty hitting/righty throwing first base profile is historically awful, but Vaughn has enough bat to make it work.”

It probably didn't help that the Sox rushed him to the big leagues, essentially using the Schaumburg alt site experience during the 2020 pandemic as his Double-A and Triple-A seasons wrapped into one. And he had a decent run from 2021-24 before hitting hard times this season.

It's not often a five-year veteran is sent to Triple-A at age 27 to work on his game, but that's what the Sox did on May 23. The Brewers sent Vaughn to their Triple-A Nashville affiliate Friday.

In hindsight, it feels like Vaughn was too much of a high-floor, low-ceiling prospect. Riley Greene or C.J. Abrams would have been much better picks. It also doesn't speak well to the Sox' player development that the most successful hitter from the 2021 playoff roster is Gavin Sheets, a second-round pick in 2017 now in his first year with the Padres.

So it's time to decide which of the White Sox first-rounders is most regrettable. These aren't necessarily bad players or the wrong selection in the moment, but they clearly did not pan out:

1) Catcher Kurt Brown, No. 5 overall in 1985

The selection of Brown is notable mostly because Barry Bonds went to the Pirates with the very next pick. Drafted out of high school, Brown ended his career at Triple-A Vancouver in 1991 and never played in the majors.

Could have had: Barry Bonds

2) Catcher Danny Goodwin, No. 1 overall in 1971

The Sox have had the No. 1 pick just twice in team history. Harold Baines worked out well in 1977, but Goodwin, from Peoria Central High School, didn't even sign. He was drafted No. 1 again in '75 by the Angels and had an unremarkable seven years in the majors. Two other Sox first-rounders never signed — Steve Buechele in '79 and pitcher Bobby Seay in 1996.

Could have had: Jim Rice, Frank Tanana

3) Third baseman Ted Nicholson, No. 3 overall in 1969

Still the highest a Mississippi high school player has even been drafted, Nicholson never made it past Single-A. He served two years in the military in 1971 and '72, which surely complicated the journey.

Could have had: Alan Bannister, who went No. 5 to the Angels and ended up playing for the Sox anyway.

4) Shortstop Bee Bee Richard, No. 6 overall in 1970

The Sox deserve plenty of blame for what happened here. They rushed Richard to the majors, put him at shortstop and he committed 26 errors in 68 games before being moved to the outfield. Hit .217 with 2 home runs in four seasons on South Side.

Could have had: Dan Ford, maybe? This was a bad draft.

5) First baseman Andrew Vaughn, No. 3 overall in 2019

Averaged 18 home runs over four years, so he was obviously a decent player. The number of talented guys who were on the board pushes this one up the scale.

Could have had: Riley Greene, C.J. Abrams, Corbin Carroll

6) Pitcher Carson Fulmer, No. 8 overall in 2015

He's still playing for the Angels' Triple-A team in Salt Lake City. Great arm that never panned out. Released by Sox in 2020 after posting a 6.56 ERA in parts of four seasons.

Could have had: Ian Happ went with the very next pick.

7) Outfielder Cecil Espy, No. 8 overall in 1980

He was traded to the Dodgers for Rudy Law, a regular on the 1983 playoff team, so Espy created some value.

Could have had: Kelly Gruber? Not a great year for Round 1.

8) Outfielder Courtney Hawkins, No. 13 overall in 2012

Former Texas high school player of the year from Corpus Christi never reached majors, eventually became a star for the independent Lexington Legends.

Could have had: Corey Seager

9) Pitcher Jason Stumm, No. 15 overall in 1999

Washington high schooler never made it to Triple-A.

Could have had: Alex Rios

10) Second baseman Nick Madrigal, No. 4 overall in 2018

A disappointment for the Sox, no doubt. But he did hit .300 twice before getting injured and landed one of the greatest all-time relievers, Craig Kimbrel, from the Cubs in a trade. Kimbrel didn't help much, but still.

Could have had: The WAR leader from this first round is actually Nico Hoerner, who went 24th.