Chicago Cubs: Best first round picks of the past 25 years

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Chicago Cubs, Jon Garland (Photo by Ron Vesely/MLB Photos via Getty Images) /

Here we look at the top five first-round draft picks of the Chicago Cubs since 1995.

With the MLB Draft set for this coming week, it might be a good time to look back on some of the Chicago Cubs‘ best draft picks in recent memory. Here, we’ll look at five of their best first-round picks of the past 25 years.

Chicago Cubs: Jon Garland

Jon Garland was the Cubs’ first pick, and tenth overall, in the 1997 draft, out of Kennedy High School in Granada Hills, CA. Though he was not a superstar in the major leagues, he put together a very respectable 13-year major league career, and thus his inclusion on this list.

As we know, Garland never actually threw a pitch for the Cubs’ major league club. In 1998, he struggled with the Cubs’ Rockford club in the Class A Midwest League, putting up a 5.79 ERA in 19 starts. On July 29, with the Cubs in the middle of a pennant race, the team traded Garland to the Chicago White Sox for reliever Matt Karchner.

Karchner wasn’t particularly great for the Cubs in 1998, posting a 5.14 ERA in 28 innings, and he also pitched for them a little in 1999 and 2000. Garland, meanwhile, made his major league debut in 2000 and was a dependable starter for the White Sox. Between 2002 and 2007, he made at least 32 starts for them every year. His best year, by far, was that magical 2005 season on the south side, as Garland posted a 3.50 ERA while setting a career-high with 18 wins and 221 innings pitched.

Garland also pitched for the Los Angeles Angels, Arizona Diamondbacks, and Los Angeles Dodgers before last appearing with the Colorado Rockies in 2013. Overall, he collected 136 wins.

Chicago Cubs: Kerry Wood

To this day, Cubs fans lament what might have been had Kerry Wood not had to deal with so many injuries throughout his career. Still, he had a distinguished career, most of which was spent with the Cubs, and that’s why he still deserves to be on this list.

With the fourth overall pick in 1995, the Cubs selected the big right-handed pitcher out of Grand Prairie High School in Texas. As many fans remember so well, he made a big splash right away when he arrived in the majors in 1998, throwing a complete game one-hit shutout while striking out a record-tying 20 batters against the Houston Astros in just his fifth major league start.

It was part of a 1998 campaign in which he won Rookie of the Year, winning 13 games while posting a 3.40 ERA and leading the league in hits allowed per nine innings and strikeouts per nine innings. Unfortunately, he then had to sit out the entire 1999 season due to injury.

When Wood came back, he was a trustworthy and reliable starting pitcher for a few years, including that incredible 2003 season in which he led the league in strikeouts. However, injuries started taking their toll again shortly after, and by 2007 Wood had to reinvent himself as a reliever. He was the team’s closer during the team’s 2008 NL Central Championship season.

Wood left for the Cleveland Indians in 2009 and also made a stop with the New York Yankees before finishing his career back on the north side of Chicago in 2011 and 2012, again as a middle reliever. Injuries aside, it was already an excellent career and ended up being a great draft choice.

Javier Baez, Chicago Cubs (Photo by Rich Schultz/Getty Images) /

Chicago Cubs: Javier Baez

Javier Baez was the last first-round draft pick of the Jim Hendry era when the Cubs selected him ninth overall in 2011, out of Arlington Country Day School in Jacksonville, FL. It’s hard to imagine now, but for years Baez was at the center of trade speculation. Would he fit into Theo Epstein’s plans?

This was especially true after Baez made his debut with the big league club at the end of 2014, and he struggled to make contact at the plate. With Addison Russell and Starlin Castro already available to play middle infield, many thought Baez would be the odd man out. Instead, it ended up being Castro, who is a good hitter in his own right. Yet the decision to hold onto Baez has paid off.

Baez tore up the Triple-A Pacific Coast League with Iowa in 2015 before spending a little time with the big league club again. He got a chance to play regularly in 2016, showing improvement at the plate and constant highlight-reel defense. The 2016 postseason was primarily considered to be a breakthrough for him on the national stage. He then continued to show improvement in 2017 before putting in all together in 2018, finishing second in NL MVP voting.

Baez’s skills on both offense and defense have made him a fan favorite, and he has seemed to become a smarter player each year. It remains unclear whether Baez and the Cubs will be able to get a long-term contract extension done, though most Cubs fans are pulling for it to happen, as he still figures to have many solid years left.

Chicago Cubs: Kris Bryant

Building a championship team takes a lot of hard work and requires some good decisions. In many cases, it also requires things to align in your favor. One of the Cubs’ most important pieces of their 2016 championship team came because of that.

Kris Bryant was the Cubs’ first pick – and second overall – in the 2013 draft, from the University of San Diego. The Houston Astros, instead of selecting one of the most hyped bats in a long time, decided to go with pitcher Mark Appel with the first overall pick. Appel was a colossal bust, never making it to the majors.

Bryant, meanwhile, quickly made his way through the Cubs’ minor league system and, in the eyes of most observers, earned a spot with the big league club out of camp in 2015 (though we know the story behind that). Still, Bryant arrived early in 2015 and had a tremendous rookie season that earned him NL Rookie of the Year, batting .275 with 26 home runs and 99 RBIs.

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Bryant had an even better offensive season in 2016 and, mainly on the strength of his willingness to play the outfield along with third base, won NL MVP honors as the Cubs won the World Series. Though he didn’t hit for as much power in 2017, Bryant improved his OPS that season from the year before.

Bryant was slowed by injuries in 2018 but bounced back to have an excellent 2019 season still. He was the subject of daily trade rumors this past offseason, but the club decided to hang on to him for now. If Bryant does stay with the team long-term, he has a chance to be an all-time great hitter in team history. For now, considering all he’s accomplished with the Cubs, he has to be considered among their best first-round picks in recent years.

Chicago Cubs: Josh Donaldson

Josh Donaldson owns the highest career WAR of any Cubs first-round draft pick since Rafael Palmeiro from the 1985 draft. Unfortunately, his success has come elsewhere. Still, he has to be considered among the Cubs’ best first-round picks.

Donaldson was a supplemental pick, 48th overall, in 2007. It was a pick that the team received as a result of losing Juan Pierre to free agency. Donaldson was drafted as a catcher out of Auburn University, though he hasn’t caught much in the majors, eventually becoming a third baseman primarily.

Seeing a significant opportunity to win it all in 2008, Donaldson was part of a four-player package that the Cubs sent to the Oakland Athletics on July 8 for pitchers Rich Harden and Chad Gaudin. Harden was the big prize in that trade, and he was great for the Cubs down the stretch, posting a 1.77 ERA in 12 starts.

However, Harden’s career quickly fizzled after that while Donaldson’s took off, making this trade one that Cubs fans lament to this day. Donaldson signed with the Minnesota Twins this past offseason but has seen time with the A’s, Toronto Blue Jays, Cleveland Indians, and Atlanta Braves. He won the AL MVP award with Toronto in 2015 and overall has had six seasons of at least 24 home runs and five seasons of over 90 RBIs.

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At age 34, Donaldson remains a reliable offensive force and, when play resumes, figures to do a lot more damage in that dangerous Minnesota lineup. Though he never did anything with them, Donaldson is among the most successful first-round picks the team has ever had.

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