Evaluating the Career Path for Each of the Last Six Number One Overall Picks

Recently, the 2026 MLB Draft first-overall pick, Roch Cholowsky , was sent to the 7-day Injured List. Cholowsky is likely done for the season due to wrist soreness. The Chicago White Sox plan to get at-bats right after being drafted has become fairly standard for 1.01s since COVID. Each first overall pick since 2020 has started their career directly after being drafted.

The Chicago White Sox took Roch Cholowsky with the first overall pick in July of this year. Cholowsky was the wire-to-wire top prospect going into the draft . The former UCLA Bruin entered pro ball with plenty of hardware. He's a three-time All-American, two-time Big Ten Player of the Year, and a Golden Spikes finalist. Still, in nine games, the shortstop hit .167 with only one homer. He did manage to drive in 10 runs. His struggles could be tied to his injury and the adjustment to pro ball. This career start should not leave White Sox fans worried, however.

Cholowsky was one of the top college prospects and prospects overall in the 2026 Major League Baseball Draft for good reason. He has the potential to have four-plus tools. He hit over 20 home runs in his last two seasons at UCLA. Not to mention, he was also awarded Big Ten Defensive Player of the Year at shortstop. The only knock is his average speed. He has the Baseball IQ to offset his lack of speed. Even with a disappointing career start, he's still the future on the South Side of Chicago.

Eli Willits was taken number one overall by the Washington Nationals in the 2025 MLB Amateur Draft. The Nationals had recently fired their GM, and Willits was the first pick of the new regime at the head of baseball operations. Willits comes from a baseball family . His dad played six seasons with the Angels and now coaches at Oklahoma, where Eli's brother played college ball. Willits' professional career started strong. In just 15 games after being drafted, Willits hit .300 with two extra-base hits in Single-A.

Willits continued his strong start heading into this season. According to MLB Pipeline, Willits is now the fourth-ranked prospect in all of baseball thanks to his five-tool potential. The power that many scouts were worried about has shown up in games with over 40 extra-base hits this season. On the bases, he has been outstanding, stealing nearly 60 bases so far. At the plate, he shows the discipline and contact skills to be an above-average hitter for the rest of his career. The switch-hitter handles himself well in the field as well, with above-average actions and a solid arm.

Travis Bazzana – 2B (Cleveland Guardians)

The Guardians took Travis Bazzana , an Australian infielder, out of Oregon State in the 2024 MLB Amateur Draft. Shortly after, the Aussie joined the Guardians' High-A affiliate, the Lake County Captains. Bazzana homered in his first game as a captain and showed some serious potential to start his career. In 27 games, Bazzana batted .238 with three home runs and seven doubles. The second baseman also helped lead the Captains to their first Midwest League title since 2010 to start his career.

Bazzana was named to the first all-star team of his career during his rookie season this year. Bazzana is hitting. 235 on the season with nine home runs. Long-term, he profiles as an above-average hitter thanks to his discipline, bat speed, and compact swing. He should produce average power numbers thanks to the aforementioned power. Unfortunately, in the field, the Guardians hope that he's at least average at second base for his career. He has a below-average arm and gets caught in between hops on the dirt.

Paul Skenes has had the most successful pro career so far of the group. The Pittsburgh Pirates took Skenes in the 2023 MLB Draft. He is a three-time All-Star, Rookie of the Year Winner, and a Cy Young recipient. Some could have predicted this start to his career after his junior year at Louisiana State University (LSU). He won the College World Series as a junior, where he pitched 122 2/3 innings and struck out 209 batters. He continued this success in his first year of pro ball that same season. He threw only 6 2/3 innings in his first summer after being drafted but struck out 10 batters during that stretch.

When Skenes made his MLB Debut in 2024, the Pittsburgh Pirates became the only team to have a number one overall draft pick pitcher throw a pitch to a number one overall draft pick at catcher. In his first two seasons, he dominated opposing batters, pitching to a sub-2.00 ERA in both seasons and striking out over 10 batters per nine innings. He has regressed this season, posting nearly a 4.00 ERA due to a velocity dip and control issues. He will look to address some mechanical flaws heading into next season.

Henry Davis is the other half of the number-one overall pick battery the Pittsburgh Pirates selected. Davis was drafted in 2021 out of Louisville University. A lot of scouts were split on whether or not Davis was even a top-15 pick coming out of college that season. However, the Pirates selected Davis with the number one overall pick as a hit-first athletic catcher. They even signed Davis at a discount, which helped them sign some of their later picks. Freshly after being drafted, Davis only played eight games in the Pirates' system. During that time, he made an impact, however, hitting three home runs and batting .308.

Davis has been an enigma in Pittsburgh. Drafted as a hit-first catcher, he has developed into one of the better defensive catchers in all of baseball. This season alone, he has a 46% caught-stealing rate. However, he has struggled at the plate. He has yet to reach the 10-homer mark in his career and has a career batting average of .177. The former walk-on is a positive influence in the clubhouse and beloved by his pitching staff, but he needs to produce more at the plate to realize the potential career some scouts saw for him.

Jackson Holliday – 2B/SS (Baltimore Orioles)

The Orioles took the eldest son of former All-Star Matt Holliday in the 2022 MLB Draft with the first pick. Jackson Holliday quickly established himself as one of the best hitting prospects in baseball. In the same season he was drafted, Holliday started his career with two teams in the Orioles' system. The Orioles' second baseman played in 20 games and showed off his elite high school hit tool. Across those 20 games, he hit .297 and walked twice as many times as he struck out. He even added five doubles to his early career resume in his first taste of pro ball.

Before Jackson Holliday's MLB debut, Holliday was considered the top prospect in all of baseball , even ahead of the aforementioned Paul Skenes. Since then, Holliday has dealt with a plethora of injuries during his career. He's in his third season and will likely eclipse the 110-game mark once across those three seasons. When he's on the field, he's produced more power than many expected. Unfortunately, the hit tool is not what others expected. He doesn't walk often and doesn't track out more than many scouts expected. If Holliday can put together a fully healthy season, he will turn 23 before next season, and we could see his potential on display.

Main Photo Credit: Patrick Gorski-Imagn Images