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White Sox Deep Dive: Rookie League Left Fielders

Benyamin Bailey leads this list of outfield hopefuls.

Benyamín Bailey hopes to bounce back in 2022.
| Sean Williams/South Side Sox

“Deep Dive” focuses on the depth of each position in the Chicago White Sox organization.

Welcome to another year of Deep Dive, where we analyze the past, present and future for each position in the White Sox organization. Each position is broken into five parts:

  1. Depth in the rookie levels (Dominican through Arizona)
  2. Depth in A-ball (Kannapolis and Winston-Salem)
  3. Depth in the higher levels (Birmingham and Charlotte)
  4. Under the Radar-type detail on a White Sox player
  5. Free agent options

Left field is considered, along with shortstop, one of the weakest in the Sox organization. Only one farmhand is ranked among the Top 30 in the White Sox organization, Blake Rutherford, and he’s actually been descending their list.

This list doesn’t include Erick Hernández, who is the 28th-ranked international prospect per MLB Pipeline and is compared to a young Juan Soto (the official announcement of his signing won’t take place until January).

Below are the organization’s left fielders who finished the season at either the Arizona Complex League (ACL) or Dominican League (DSL).

Ages below are as of April 1, 2022


ACL White Sox

Benyamín Bailey
6´4´´
215 pounds
Age: 20
Bats/Throws: R/R
Other positions played: RF
2020 SSS Top Prospect Ranking: 26
2021 SSS Top Prospect Ranking: 12

Bailey, a native of Panama, received a minimal $35,000 signing bonus from the White Sox on April 27, 2019, with literally no fanfare. However, by the time he ended his first pro season five months later, Bailey was the best-known prospect on the entire DSL roster and considered a rising star. In 55 games totaling 185 at-bats, Bailey slashed an incredible .324/.477/.454 with 12 doubles, three triples, two homers, 19 RBIs, 52 walks (21.4%), 40 strikeouts (16.5%), 10 stolen bases and 166 wRC+. Bailey’s OBP was hovering around .500 for most of the year, before a late-season slump dropped him to .477. With that said, Bailey still led the league in that department and was near the top in walks and OPS as well.

In most cases, the DSL leaders are either returning players and/or are much older than the league average; in Bailey’s case, this was his first year in professional ball and he was about six months younger than his competition. As a result of his debut, he moved up to 19th in the team’s 2020 prospect rankings.

Nearly everything that went right for Bailey in 2019 went wrong for him in 2021. In part due to the 2020 season lost to the pandemic, the slugger was given an aggressive assignment, to Low-A Kannapolis, where he floundered; unfortunately, he did no better after a demotion to Arizona, making 2021 a truly lost season. In a combined 61 games totaling 202 at-bats, Bailey slashed just .193/.303/.272 with two doubles, one triple, four homers, three stolen bases, 31 walks (16.0%), 71 strikeouts (30.7%) and 87 wRC+. He still walked at a tremendous clip, but fanned much more frequently while producing a far lower average. While the competition was a bit more difficult, the likely contributors to his down season were the long layoff and adjusting to a new culture.

When MLB Pipeline ranked him among the organization’s Top 20 prospects in 2020, they gave him the following grades: 50 for hitting, power and fielding; 45 for running and arm. With his large frame, one would expect more than six homers in 116 career games. He hasn’t taken advantage of his raw power yet, as he has hits grounders at a 53% clip when he does make contact. Hopefully with experience, Bailey can add some loft to his swing and lay off the low offerings. He does run well for his size, but expects to slow down as he gets older. Bailey’s arm is considered fringy at best, so even though he’s split time between left and right field, he’s better suited in left.

No longer ranked among the system’s Top 30, Bailey can easily return to that list with a productive 2022. It wouldn’t be surprising to see him begin next season with an extended spring training stay in Arizona, and move up to Kannapolis once a Cannon Baller is promoted to Winston-Salem.


DSL White Sox

Roberth Gutierrez
6´0´´
170 pounds
Age: 20
Bats/Throws: R/R
Other positions played: 1B, 3B, RF

As a 17-year-old native of Maracay, Venezuela, Gutierrez’s first taste of professional ball came in 2019, and he acquitted himself relatively well by slashing .274/.365/.378 in 47 games with four doubles, five triples, 15 RBIs, seven stolen bases, 21 walks (15.6%) and 33 strikeouts (24.4%). Gutierrez had nine assists as opposed to two errors, so it appears he has a solid arm. His numbers got lost when compared to the DSL squad’s other two outfielders (Bailey and Johnabiell Laureano), but while he may not have the higher ceiling of those two guys, Gutierrez seems to fit the bill of a reserve outfielder due to his lack of power and game-changing speed.

After returning to the DSL for the 2021 season after 2020’s pandemic shutdown, Gutierrez’s numbers surprisingly slipped. In 33 games totaling 99 at-bats, he slashed .232/.387/.303 with one double, three triples, seven stolen bases, 24 walks (19.4%), 31 strikeouts (25.5%) and 110 wRC+. Actually, his wRC+ was identical to 2019’s but considering he was now a year older than the average competition, it’s a slight setback. Offensively, though, Gutierrez did show more patience at the place by significantly increasing his walk rate. On the defensive side of the equation, he showed good versatility in playing all infield and outfield corners, and could be viewed as an organizational outfielder down the road. He again displayed a solid arm by gunning down six runners from the outfield.

Expect Gutierrez to begin the 2022 season in the ACL.

Carlos Gomez
6´0´´
180 pounds
Age: 20
Bats/Throws: L/L
Other positions played: CF, RF

On Sept. 11, 2019, this Dominican native signed a minor league contract with the White Sox. Due to the 2020 pandemic shutdown, however, Gomez didn’t enter his first professional action until this year. The rustiness showed, as he slashed just .179/.317/.179 in 28 games with five stolen bases, 12 walks (14.6%), 26 strikeouts (31.7%) and 63 WRC+.

On the positive side, Gutierrez’s did heat up a bit in September by hitting .276 with a .405 OBP. His strength may be his defense, as in playing all three outfield positions he provided six assists while committing just one error. While it’s possible Gutierrez’s begins 2022 in the ACL, he’s more likely to return to the DSL instead to hone his offensive skills.

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