2 prospect busts that hurt the Cubs and 1 that helped them win a World Series

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It’s fun to look at prospects and expect a lot. Yesterday we posited that Pete Crow-Armstrong could do what Bobby Witt Jr. has done on his way to an 11-year $288 million dollar extension. We’ve also continued to hype former prospects in the hope of a bounceback like Nick Madrigal.

However, MLB.com recently posted an article that looked at fifteen prospects that they were woefully wrong about and there are three that jumped out to me as a Chicago Cubs fan for one reason or another.

The list was broken into two categories of failure: Whiffs and Foul Tips, with whiffs being complete misses and foul tips just not quite living up to their lofty billing.

Bobby Brownlie RHP- Whiff

Brownlie is the player that has the most obvious impact on the Cubs considering he was their first-round draft pick in the 2002 Draft. He was selected out of Rutgers University and he was paired with 2001’s first-round pick, another college righty named Mark Prior to be the future of the Cubs rotation.

He carried a career 4.28 ERA in the minors and never made it above AAA but he was ranked as highly as number 38 on the MLB Pipeline Top 100 list.

Jonathan Mayo had this to say about Brownlie:

He had a solid first season in 2003, landing in the Top 50. He followed it up with a strong showing in Double-A the following year, though he never missed a ton of bats.
Jonathan Mayo, MLB.com

The status backed that up with his career average being just 6.8 K/9.

Ian Stewart 3B- Foul Tip

This one requires a bit of extra digging to understand why this player means anything to the Cubs. He was ranked as highly as the number two prospect in baseball in 2005, so when the Cubs traded for him in 2012 some of his prospect shine had faded.

However, there was still hope. This was the first relatively important deal of the Epstein/Hoyer regime and it saw the Cubs try to help Stewart regain his footing on a rebuilding team in return for a relatively unknown soft-hitting middle infield prospect named DJ LeMahieu.

Epstein didn’t make many deals that ended up looking bad in the long run but this is definitely one of them. LeMahieu would go on to be worth 31.5 WAR over his 13-year MLB career (that’s still going), whereas Stewart would only play one season (55 games) for the Cubs in 2012 and only 24 more games in his career for the Angels in 2014.

That being said, if the Cubs had kept LeMahieu there’s nothing that says that the Cubs would subsequently make the trade for Addison Russell, or have a poor enough season to draft Kris Bryant or Kyle Schwarber (who we’ll hear about again later).

While this trade looks awful on paper, in baseball everything happens for a reason.

Tyler Kolek RHP- Whiff

Kolek was the number two overall pick in the 2014 MLB Draft. He rose as high as the 27th best prospect in baseball in 2015. There was allegedly strong consideration for Kolek at number three that season for the Chicago White Sox which could have left Carlos Rodon who was strongly linked to the Cubs available as the fourth pick.

Fortunately, the Marlins took Kolek, the White Sox took Rodon and that left Kyle Schwarber available as the Cubs target at four. They would sign Schwarber to an under-slot deal that would allow them to draft three high school pitchers to over-slot deals later in the draft.

One of those pitchers was Dylan Cease who the Cubs would go on to trade to the White Sox in an effort to keep their window of contention open.

Another of those pitchers was the Cubs’ current ace and 2023 Cy Young contender Justin Steele.

What does it mean?

Baseball is hard. Finding prospects that have all of the necessary skills to be successful is hard. But having those prospects actually put all of that together for prolonged success is the hardest thing of all.

Could the Cubs have a career 30-WAR player in their farm system?

Maybe.

But it might not be who you’d expect.

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