Thinking Back on Some Cubs Prospects Who Broke My Heart

My history as a Cubs fan dates back to the Kerry Wood Game, and my history as a minor league baseball fanatic dates back to 2000.

My Dad and I went on a baseball trip that summer, including a stop in Peoria for a Chiefs game. The Chiefs third baseman had a good game, and my Dad wrote in my scorecard he liked his swing. Just a year later, I watched as that third baseman won the Rookie of the Year, terrorizing the Cubs in the process.

I was hooked. There was a way to anticipate stars before they were stars??? This is my own origin story, and I tell it to give you an idea of the timeline of today’s article: the Cubs prospects who broke my heart along the way.

Corey Patterson was the first one, but my introduction to him was really once he’d already debuted in Wrigley. He was my first example that, yes, the can’t-miss sometimes do for a variety of reasons. But it didn’t really sting in the way that others in the last 20 years have.

So step into my own not-so-pleasant memory lane, and here’s who those guys were for me.

Bobby Hill. My Dad was a White Sox fan, and a Baseball America reader, and so he pushed Bobby Hill hard after the Cubs signed a guy the White Sox couldn’t.

Hill had used the then-popular Scott Boras tactic of playing independent ball, with an 81-steal, 101-walk season for the Newark Bears in 2000 (on a roster that also included Joe Borowski, oddly enough). The idea of the Cubs getting a quick guy with actual on-base skills was so great as Patterson began to flop. What’s so interesting to me about what happened to Hill is that it wasn’t the skills he lacked that held him back, it was that his plus traits just didn’t translate. Just 48 walks and 6 steals in 249 games. I still can’t believe that was it it.

But hey, he brought us Aramis and Kenny. So maybe it wasn’t that heart-breaking after all.

Justin Jones and Andy Sisco. I saw the 2oo3 Lansing Lugnuts in Kane County, and I can’t remember which of these two I saw, but I remember being enamored with both.

They were my first examples of raw pitching prospects with big strikeout rates, and especially the first example of how you dream a little more when it’s a left-hander for some reason. When the Nomar trade happened, I was happy, but I remember being disappointed Jones was included. Sisco became my introduction to the Rule 5 Draft; oh I was apoplectic after he was lost and had that good 2005 season.

Brian Dopirak. Dan Vogelbach before Dan Vogelbach.

Dopirak’s 2004 season has to be one of the great ones in Midwest League history. I mean, who hits 39 home runs in that league?! At that point, I was writing about prospects in tiny Internet corners, and I’m quite sure there’s me putting an 80 Grade on Dopirak’s power somewhere. I hope it’s been deleted. Dopirak’s 2005 season, a .671 OPS in the Florida State League, is one of those Great Disappointments that you get when you follow prospects enough, and one that even in hindsight I can’t completely explain.

Josh Vitters. I always had some bit of healthy skepticism when it came to Vitters, I recall, but he had a habit of winning you over. The big 2009 in Peoria, that 2011 performance in the Arizona Fall League. I remember thinking in Iowa in 2012 that the walks were starting to come. But boy was he lost in Chicago that fall. It’s hard to believe that was it, those 36 games, none with more than a single hit. By this point Aramis Ramirez had ended the Cubs third base drought, and yet, Vitters being another failed hot corner prospect hurt more.

We only recently learned that an undiagnosed medical condition may have been a huge reason Vitters never flourished. Damn.

I think you just kind of need to end with Vitters. There were other guys I could point to – Hak-Ju Lee, Brett Jackson, Josh Donaldson, Donnie Veal – but I’m not sure we need anymore negativity. The good news is the 2010s weren’t littered with so many disappointments!

[Brett: Can I just throw in a mention of Angel Guzman and Juan Cruz? Each had some big league success as relievers, but man, they were supposed to be THE GUYS in the rotation in the mid-2000s. Also, I’m glad you mentioned Brett Jackson, because I was CONVINCED that being so tooled out was going to make him, at the absolute worst, an extremely good 4th outfielder, despite the extreme contact issues. And surely a prospect isn’t doomed as a future starter just because his AAA contact rate was nightmarish ….]

written by

Bryan Smith is a Minor League Writer at Bleacher Nation, and you can find him on Twitter at @cubprospects.

more cubs news

Chicago Cubs Lineup: Pete Crow-Armstrong Gets a Start

CUBS LINEUP — The Cubs won again last night, which means they've already won the season-series against the still-struggling Astros. Justin Verlander will be on the bump for today's finale, but he'll have to go up against the mighty Javier...

The Leadoff Role, Cubs Front Office is Not Particularly Well-Liked? And Other Cubs Bullets

It's a pretty big day for the Chicago Bears, eh? For the second year in a row, they own the No. 1 overall pick in the draft. Only this time, they actually plan to use it (and on a quarterback,...

Chicago Cubs Sign Brazilian-Japanese Pitcher Daniel Missaki Out of Mexican League

That's a geographic mouthful right there, and it underscores what an interesting signing this is. Stray signings throughout the year are not uncommon, particularly as injuries accumulate down on the farm and the Chicago Cubs have the ability to take...

Do the Cubs Have a Scoring-Late Problem?

Once a month since August of 2016, my friends and I get together for "Supper Club." It's like book club, but instead of reading books, we go to a different restaurant in the city. Last night, we hit our 77th...

Enhanced Box Score: Cubs 4, Astros 3 – April 24, 2024

The Cubs did all their scoring in the first, and made it stand up for the win with generally good pitching and generally good defense. Jameson Taillon looked solid again in his second start, locating well, giving up no barrels,...

Dansby Swanson with a First Inning Three-Run Homer

For the second straight night, the Cubs are jumping all over the Astros in the first inning. After a couple hits from Nico Hoerner and Ian Happ to get things going, Michael Busch hit a sac fly, Christopher Morel walked,...

Welcome Back to Iowa, Brennen Davis: Rocket Homer in His First Game Post-Rehab

What a road it's been - continues to be - for Cubs outfield prospect Brennen Davis. The former top prospect was on a rocket ship to Triple-A in 2021, and then mostly lost the last two years to various injuries....

CRAAAAAP: Cody Bellinger to the Injured List (UPDATES)

So much for all those words of optimism and negative X-rays. After colliding with the outfield wall last night, Cody Bellinger fractured his rib (Update: It's actually TWO fractured right ribs) and will hit the injured list today. Chicago Cubs...

Chicago Cubs Lineup: What is it, June 2023?

CUBS LINEUP — The Chicago Cubs took Game 1 against the Houston Astros in convincing fashion last night. So tonight, they'll go for the quick series win against Spencer Arrighetti at Wrigley Field (it'd be a good idea to win...

Bellinger Optimistic Post-Injury, Busch’s Defense, Almonte Stock Rising, Tauchman Slugging, and Other Cubs Bullets

Ed. Note: Since this article was published, a CT scan revealed a rib fracture for Cody Bellinger, who is now on the Injured List. You can find all the details of that news in our most recent article right here....

Latest News

76ers vs. Knicks: Start Time, Streaming Live, TV Channel, How to Watch

The Philadelphia 76ers and New York Knicks are playing in the opening round of the NBA Playoffs, with Game 3 up next.The Knicks beat the 76ers 104-101 on Monday when they last met. Jalen Brunson led the Knicks in the...

Donovan Mitchell Player Props: Three-Pointer Props and Odds vs. the Magic – NBA Playoffs Game 3, Thursday, April 25, 2024

At 7:00 PM ET on Thursday, in Game 3 of the opening round of the NBA playoffs, it'll be the Cleveland Cavaliers against the Orlando Magic, with Donovan Mitchell needing four trifectas to beat his 3-pointer over/under.Donovan Mitchell's Three-Pointer Prop...

Caris LeVert Player Props: Three-Pointer Props and Odds vs. the Magic – NBA Playoffs Game 3, Thursday, April 25, 2024

On Thursday at 7:00 PM ET, the Cleveland Cavaliers play the Orlando Magic in Game 3 of the opening round of the NBA playoffs, and Caris LeVert's 3-pointer over/under for this matchup requires just one trey.Caris LeVert's Three-Pointer Prop Odds...

Josh Hart Player Props: Three-Pointer Props and Odds vs. the 76ers – NBA Playoffs Game 3, Thursday, April 25, 2024

To beat his 3-point prop, Josh Hart needs to make two from downtown on Thursday, when his New York Knicks meet the Philadelphia 76ers in Game 3 of the opening round of the NBA playoffs, tipping off at 7:30 PM...

Jalen Brunson Player Props: Three-Pointer Props and Odds vs. the 76ers – NBA Playoffs Game 3, Thursday, April 25, 2024

The New York Knicks face the Philadelphia 76ers on Thursday at 7:30 PM ET in Game 3 of the opening round of the NBA playoffs, and if the Knicks' Jalen Brunson drains three 3-pointers, he'll beat his over/under.Jalen Brunson's Three-Pointer...

Donte DiVincenzo Player Props: Three-Pointer Props and Odds vs. the 76ers – NBA Playoffs Game 3, Thursday, April 25, 2024

To beat his 3-point over/under, Donte DiVincenzo needs to make four from downtown on Thursday, when his New York Knicks play the Philadelphia 76ers in Game 3 of the opening round of the NBA playoffs, beginning at 7:30 PM ET.Donte...

Joel Embiid Player Props: Three-Pointer Props and Odds vs. the Knicks – NBA Playoffs Game 3, Thursday, April 25, 2024

To beat his 3-point prop, Joel Embiid needs to make two from beyond the arc on Thursday, when his Philadelphia 76ers meet the New York Knicks in Game 3 of the opening round of the NBA playoffs, starting at 7:30...

Tyrese Maxey Player Props: Three-Pointer Props and Odds vs. the Knicks – NBA Playoffs Game 3, Thursday, April 25, 2024

The Philadelphia 76ers play the New York Knicks at 7:30 PM ET on Thursday, in Game 3 of the opening round of the NBA playoffs, and one of the 3-pointer over/unders available for this matchup requires four trifectas from Tyrese...

Franz Wagner Player Props: Three-Pointer Props and Odds vs. the Cavaliers – NBA Playoffs Game 3, Thursday, April 25, 2024

Franz Wagner needs to make two 3-pointers to beat his over/under when the Orlando Magic meet the Cleveland Cavaliers on Thursday at 7:00 PM ET, in Game 3 of the opening round of the NBA playoffs.Franz Wagner's Three-Pointer Prop Odds...

Tobias Harris Player Props: Three-Pointer Props and Odds vs. the Knicks – NBA Playoffs Game 3, Thursday, April 25, 2024

At 7:30 PM ET on Thursday, in Game 3 of the opening round of the NBA playoffs, it'll be the Philadelphia 76ers against the New York Knicks, with Tobias Harris needing two trifectas to beat his 3-pointer over/under.Tobias Harris' Three-Pointer...

more cubs news

Latest News