Ranking the last 10 Chicago Cubs first-round draft picks, from worst to best

The Chicago Cubs currently have a healthy farm system, with seven players in MLB Pipeline's Top 100 prospects list. This is partially due to the team turning a corner on evaluating young players and hitting on some of their high draft picks.

A lot of these draft picks are on the cusp of the majors or have already debuted in Chicago, contributing to the top-heavy farm. The last four drafts have yielded fantastic results, in contrast to the team's previous efforts in the 2010's, especially in the pitching department.

To highlight this turnaround, I'm going to rank the last ten first-round draft picks taken by the Chicago Cubs based on how the players turned out and their value to the team through contributions/trade value.

10. RHP Ryan Jensen: 27th overall in 2019

The Cubs selected right-handed pitcher Ryan Jensen 27th overall in 2019, and the organization seemed to project him as a starting pitcher in the majors for a while. But his small 6'0 190-pound frame and command issues hindered those chances.

In Jensen's 272 1/3 innings pitched across all levels of the minor leagues, he sports a career 4.49 ERA and a 328:188 strikeout-to-walk ratio. The high strikeout totals are nice on paper but do not make up for the insane amount of walks issued by the former Cubs farmhand.

After failing to establish himself as both a starter and reliever with the Cubs, Jensen was placed on waivers in 2023. After brief stints with the Seattle Mariners and Miami Marlins, Jensen made his way to the Minnesota Twins. In 2024, he made 44 appearances for Minnesota's Triple-A affiliate, where he again continued the high strikeout, high walk pattern.

Unfortunately, the Cubs overprojected Jensen's abilities and they were unable to cash in on a notoriously stacked 2019 draft class. Some of the players selected after Jensen that year include 2024 All-Star Gunnar Henderson (42nd), Yankees shortstop Anthony Volpe (30th), White Sox catcher Korey Lee (32nd) and current Cubs first baseman Michael Busch (31st).

9. SS Ed Howard: 16th overall in 2020

This was a pick that should have netted the Cubs a future cornerstone of the big-league roster. Jed Hoyer was on the cusp of starting a rebuild and there were plenty of quality players to choose from in the class, including Pete Crow-Armstrong.

But the team opted for the hometown kid Ed Howard, a 6'2 shortstop who was drafted out of Mount Carmel High School. Drafting hitters out of high school is fairly risky in general. But taking one 16th overall and committing $3.745 million to him, only for him to completely come up short is not a good look.

At 22 years old, Howard has failed to make it further than the High-A South Bend Cubs in his four years with the organization. Howard also features an ugly career slash line of .225/.281/.298 in 260 Minor League games, with 22 stolen bases and 46 extra-base hits. This is certainly the most disappointing first-round selection since Jed Hoyer took over the front office in 2019.