Latest News: Cubs’ Greatest First-Round Pick?

As Major League Baseball’s Draft season takes center stage, Chicago Cubs fans are once again reflecting on one of the organization’s most intriguing historical questions: Who is the greatest first-round draft pick in franchise history?

The discussion was recently highlighted in BCB After Dark, the Cubs’ popular late-night community forum, where fans were invited to debate which first-round selection has made the greatest impact on the organization. While there is no shortage of memorable names, the answer is far from straightforward, especially when balancing individual accomplishments with contributions made specifically while wearing a Cubs uniform.

The conversation comes at an appropriate time as MLB Draft Week generates renewed interest in the importance of amateur scouting and player development. For every future superstar selected, teams hope they have found the cornerstone of their franchise, though history shows that drafting successfully is often easier said than done.

For the Cubs, the MLB Draft has produced mixed results over the decades.

The amateur draft was introduced in 1965, and for much of its early history Chicago struggled to consistently identify elite talent. Those draft shortcomings played a significant role in the franchise’s prolonged championship drought, as the organization often failed to build a sustainable pipeline of homegrown stars.

Fortunately for Cubs fans, the club’s drafting strategy improved dramatically beginning in the late 2000s. Many of the players selected during that period eventually became key contributors to the team’s historic 2016 World Series championship, either by starring on the field or serving as valuable trade assets that helped complete a championship-caliber roster.

Determining the greatest first-round pick, however, depends largely on the criteria being used.

Looking strictly at career value, several names immediately stand out but not all of them actually built their legacies in Chicago.

Hall of Fame slugger Rafael Palmeiro, selected by the Cubs in the first round, ranks as one of the most accomplished players ever drafted by the organization. However, he appeared in only 258 games for Chicago before being traded away, with the overwhelming majority of his Hall of Fame-caliber career taking place elsewhere.

A similar case can be made for Josh Donaldson.

The former American League MVP was also a first-round Cubs selection but never appeared in a regular-season game for the franchise before eventually developing into one of baseball’s premier third basemen with another organization.

Because of that, many fans believe those players should not qualify when discussing the greatest first-round draft pick in Cubs history, since their greatest achievements came while wearing different uniforms.

Even Greg Maddux, arguably the greatest player ever drafted by the Cubs, presents a unique complication.

Maddux was actually selected in the second round rather than the first, immediately removing him from consideration despite eventually becoming one of baseball’s greatest pitchers. While he began his Hall of Fame career in Chicago, much of his legendary success came after leaving the Cubs in free agency.

Likewise, longtime Cubs standout Rick Reuschel also falls outside the discussion because he was selected in the third round rather than the opening round.

That leaves several modern Cubs stars as the strongest candidates.

Among the most compelling names is Kris Bryant, the second overall selection in the 2013 MLB Draft. Bryant quickly developed into the face of the Cubs’ rebuilding project, winning National League Rookie of the Year honors before capturing the 2016 National League MVP Award. Most importantly, he helped lead Chicago to its long-awaited World Series title, ending the franchise’s historic 108-year championship drought.

Many fans view Bryant as the greatest first-round selection because of both his individual accomplishments and his enormous role in the club’s championship run.

Another popular choice is Kerry Wood.

Selected fourth overall in 1995, Wood remains one of the most electrifying pitchers in franchise history. His legendary 20-strikeout game against the Houston Astros remains one of the greatest single pitching performances baseball has ever witnessed. Although injuries prevented him from reaching his full potential, Wood spent much of his career with Chicago and became one of the franchise’s most beloved players.

Javier Báez also receives strong support.

Chosen in the first round in 2011, Báez developed into one of baseball’s most exciting and entertaining players thanks to his dazzling defense, powerful bat, and unmatched flair on the field. He played a major role during the Cubs’ championship era and became a fan favorite because of his spectacular athleticism and memorable postseason performances.

Current Cubs veterans continue climbing the franchise rankings as well.

Ian Happ, selected in the first round in 2015, has quietly built one of the most productive careers among recent Cubs draft picks. His versatility, consistency, and leadership have made him one of the club’s longest-tenured players.

Meanwhile, Nico Hoerner, the Cubs’ first-round selection in 2018, continues establishing himself as one of baseball’s premier defensive infielders while providing steady offensive production and outstanding versatility.

One notable omission from many discussions is Kyle Schwarber.

Although Schwarber delivered one of the most iconic performances in Cubs history by returning from injury during the 2016 World Series, his overall value during his time in Chicago was limited compared to several other first-round selections. His defensive struggles also reduced his overall statistical value despite his tremendous power.

Ultimately, the debate has no universally accepted answer.

Some fans prioritize career statistics, while others place greater emphasis on championships, longevity, leadership, or unforgettable moments.

Whether the choice is Bryant for delivering a World Series title, Wood for his electric peak, Báez for his excitement, or one of the current stars still building their legacy, the discussion highlights just how important successful drafting has become to sustained success in Major League Baseball.

As another MLB Draft approaches, Cubs fans can only hope the organization’s next first-round selection eventually earns a place alongside those franchise-defining names—and perhaps one day becomes the next answer to this enduring debate.