Our Favorite Cubs of All Time (That We’ve Seen)

We decided that a good introduction to our readers would be our look at our favorite players that we’ve ever watched play for the Cubs. We don’t agree on too much here, but that is to be expected when looking back on two decades of surprisingly decent Cubs baseball. We may not be old enough to remember the great Ernie Banks, but that doesn’t mean these players weren’t fun to watch in their own right.


Geovanny Soto – Tommy: There really haven’t been a lot of good, or even league average catchers with the Cubs since I was born. Michael Barrett gets points for punching Pierzynski in 2006, but loses many more points for being terrible, both as a teammate and an everyday catcher. Soto’s rookie season was monstrous, and he had a couple more seasons where he was an intimidating offensive threat. Throw in his impeccable facial hair, and he’s an obvious choice for me.

Michael Barrett – Kenny: Who else do I have?  Scott Servais? Todd Hundley? Damian Miller?  This one was easy considering after Soto’s rookie year I have never trusted him at the plate….and come on Barrett punched AJ in the face.

First Base

Derrek Lee – Derrek Lee posted the best non-Sammy offensive season I’ve ever seen out of a Cub in 2005, and posted a few other very large years in his tenure with the Cubs. D. Lee strode into the batter’s box and struck an imposing, statuesque pose: open and upright, brandishing his bat high in the air, ready to unleash the full force of his 6’5” frame upon one unfortunate baseball. His beautiful swing produced all of that contact, power, and on-base goodness that makes you feel all tingly inside.

Mark Grace – Even though I was very young when I watched him I loved him.  No batting gloves and a sweet left handed swing was fun to watch. My Grandma Jo and I sat in her room when he splashed a home run in the pool in Arizona.

Second Base

Mark DeRosa – DeRosa was an integral part of a very good 2008 Cubs team. He hit for power, played competent defense, and stayed mostly healthy. I never bought into the Mark DeRosa Love Fest that the rest of the city apparently did, but I really enjoyed watching him play for the Cubs and cannot deny how important he was to the 2008 Cubs.

Mark Bellhorn Not many choices to be had it was him or DeRosa and even though Bellhorn only played 1+ year with the Cubs in 2002 he hit 27HR’s….TWENTY-SEVEN.  I was very sad when he was traded.

Third Base

Aramis Ramirez – Aramis Ramirez occasionally took swings that could only be described as reckless – his head came off the ball, the bat came through the zone with a violent, unhealthy jerking motion, and he usually missed the ball by a foot. But sometimes he made contact. Thunderous contact. The type of explosive contact that brings fans roaring to their feet as a towering fly ball soars towards Waveland Avenue.

I really miss those swings.

Aramis Ramirez – Besides RF this one was the easiest.  Aramis is the best third basemen the Cubs have had since Santo.  One of my favorite memories of him was him hitting a bomb of D-train in game 4 of the NLCS.  My favorite is the Walk off against the White Sox in 2008, I was sitting in the bleachers and received a nice beer shower.


Starlin Castro – This might be a bit premature, but Cubs shortstops have been horrendous since I was born. Besides, Castro is a fun player to watch. He has this slightly erratic nature to his swing, his throws, and everything he does on the field. He just looks like a young natural athlete scrambling to get his body in the right position at the last second. Watching Starlin continue to develop into a great shortstop is going to be a real pleasure.

Starlin Castro – First real Cub prospect that has panned out in my lifetime.  Love watching him play and he is only a few years older than me.  I was at my senior prom during his ML Debut, checked my phone and had a text from Tommy saying “CASTRO!!!”  He then told me what I was missing.

Right Field

Sammy Sosa – I don’t think I could possibly describe what Sammy meant to me when I was younger. The chase in ’98 got me into baseball. I cried as a 6 year old when McGwire broke the record first. I don’t why. I was probably too young to understand the feverish excitement that Sammy produced in 1998, but he was the guy I emulated when I swung the bat in my backyard, the guy who’s hop I used after smoking a whiffle ball over the garage, the guy who’s signature kiss to the camera I shot at random people in the hallway in elementary school. He was my sports idol through my introduction to baseball, and will always be one of my favorite Cubs.

Sammy Sosa – Do I really need to explain this one?  “Move over Big Mac, you’ve got company!”

Center Field

Corey Patterson – I went back through all of the CF’ers the Cubs have had since I was born, and could not decide which replacement-level scrub to write about here, and I was disappointed in myself. I loved Corey Patterson when he was a Cub, and he had a couple of big seasons with the club. I have vague memories of him hitting home runs and destroying his knee at 1st base, but Patterson has really drifted out of my mind over the past few year. I truly wish I could recall what good Patterson looked like, but the past 8 years of futility have painted him as a free-swinging waste of 25-man roster space.

Jim Edmonds Hate to admit it but I loved Jim Edmonds even when he was on the Cardinals.  There is something about CF’s who play elite defense that I just love.  In his short stint with the Cubs he played great.  Also that upper cut swing was something beautiful.

Left Field

Moises Alou– I pretty much avoid talking about Moises Alou nowadays. Dude was a fantastic hitter. However, every time his name pops up, Steve Bartman is brought up a few seconds later, and I still just can’t handle those feelings. Maybe someday…

Moises Alou – Well his batting stance that made it look like his ligaments were going to tear apart was pretty unique.  I liked him simply because he could flat out rake.  The lineup with Sosa, Alou and Aramis was super sexy.

Utility Guy

Reed Johnson – I considered so many names for this role, but I just had to mention Reed. He exemplified what you want out of your bench players – he played his ass off on every play and actually posted a few seasons with good numbers for the Cubs. And then he was traded as part of a package for a top prospect. Ultimate team player.

Derrek Lee – Until he injured his wrist he was one of the best Cubs I had the pleasure to watch.  ’05 Derrek Lee was one of the better performances I have ever seen.

Kenny Lofton  Part of the Aramis deal I fell in love with the man I share a name with.  He played the game the right way and although he only played a year with Chicago he was my favorite player on that ’03 team.


Mark Prior

Hate when people say he is a bust.  If he did not have injuries he may have been one of the best.  He was so good when healthy and 2003 was real fun.

Mark Prior undressed batters and dominated in ways that should not have been possible at his age. He threw powerful stuff with near-elite command for 7/8/9 innings a game. He had that competitive drive that allows #1 pitchers to remain effective late into games. He often hit pitch counts that could be deemed abusive, but that was overshadowed by the abuse he was doling out to opposing hitters. I really hope he catches on for a few more MLB innings.

Kerry Wood

Another injury guy but he was good in every role for the Cubs, as a fan we should all appreciate what he has done for the team.  Imagine a 10-year run of Prior and Wood as 1 & 2 in the rotation.

Kerry Wood is probably my favorite pitcher of all time. He possessed electric, overpowering stuff that most pitchers can only dream of throwing. His 2003 duel with Roger Clemens is one of the better pitched games I have ever watched. His Game 7 home run in 2003 was possibly the highest moment in all my baseball-watching life. It’s unfortunate that he will always be associated with injuries and unfulfilled potential, but to me Kerry Wood always embodied the hopes and dreams of the Cubs. He always returned to the team, whether after injury or being traded away, with the promise that the 20 strikeout Kid K stuff might return with him.

Carlos Zambrano 

I wish I knew what happened to him, in his early years he was so good.  When he was a #3 I loved to watch him pitch.

I love Carlos Zambrano. I know you don’t, but that’s fine as long as you acknowledge he’s one of the best pitchers in Cubs history. He’s 10th in fWAR and 9th in rWAR, he posted a 3.60 ERA in 1826 IP with good strikeout numbers. But I love him for more than his production. He was insane, possibly clinically so, and always on the edge of losing his mind on the mound. When I played the game, I had a few of the same issues on the mound, and I think I related to how he constantly talked to himself, how he had trouble with over-throwing, and how he always looked a little too big for the uniform he was wearing. Big Z pitched with a fire I’ve rarely seen, and was incredibly enjoyable to watch on the mound because of it. I know you don’t agree with that. I don’t care.

Matt Clement I used to watch him pitch with a brown piece of paper taped to my chin.  He would take the ball and compete, was very durable and real fun to watch.

Jeff Samardzija His personality is great and boy he sure can chuck it.  Glad we get to see him take the ball every fifth day.  Another guy that loves to compete, I hope all other fans appreciate guys that love to compete.

Matt Garza plays the game with a light-heartedness that is rare nowadays. He’s an extraordinarily competitive guy, but he always appears to be having fun in the dugout during games, and says all the right things after games. I hope the Cubs are able to keep him in Chicago at a reasonable price for the next 5 years or so, as he is just way too much fun to have on the team.

If I allow myself to look past his ugly departure and his horrendous and unfunny Will-Ferrell-doing-an-impersonation-of-Harry Caray impersonation, I realize that I really enjoyed watching Ryan Dempster start for the Cubs. His 2008 was fantastic, leading a very good Cubs team to the playoffs. He was a mostly consistent pitcher who racked up a good number of strikeouts without sacrificing too many walks. He was a great person on and off the field, and I would love any rotation with a Ryan Dempster type in it.

Closer – Carlos Marmol 

A few years ago he was as lights out as it comes with a slider that buckled the best hitters knees. 

Marmol used to sling the filthiest slider/slurve ever thrown, and pitchers with nasty stuff are my main attraction to the game. The slider/slurve was mid-80’s from a funky arm slot and broke what looked like a yard to his glove-side. In its prime, it broke a full horizontal 12”, and was lethal when compared with a mid-90’s heater that had 12” of arm-side run. Both pitches came out of the most unnatural looking delivery and were near impossible to pick up, meaning batters often had to guess what was coming to have a chance at making contact. And if they guessed wrong, they missed by two full feet horizontally and 10-15 mph. Filthy stuff.

Who did we leave off of the list? Let us know your favorites in the comments below!

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18 Responses to Our Favorite Cubs of All Time (That We’ve Seen)

  1. TWC says:

    Maybe it’s just *my* age, but the lack of the names “Sandberg” and “Dawson” and “(Lee) Smith” on this list are pretty glaring. I’m right with you though on many of the rest of these.

    • Tommy says:

      Hah, I maaay have made a mistake in the title, which has since been amended. This is only players we’ve seen in our lifetime, but yeah the lack of some of the more legendary players in team history is a bit jarring, for sure

  2. Cookie52 says:

    Yes, 21 is young. Sandburg was a joy to watch. Also, at the risk of being called an old curmudgeon, he played the game the right way. No ego, no bragging, no talking-just let his glove and bat do the talking.

  3. Cookie52 says:

    OK, this is not easy. Let’s give it a shot. I welcome the feedback from some of the older guys. Like Tommy, I was at Wrigley Field in diapers. Not surprising when your grandfather was a fire captain at the Waveland Fire Station. So I start in the early 60’s.

    Catcher. Randy Hundley here. Caught nearly everyday. Caught double headers in 90 degree heat. Decent hitter. I actually like Joe Girardi over Barrett or Soto.

    First Base. So many good choices. In my 21 year old mind, it should have been Leon Durham. He should have been the Derek Lee of his time. Never quite put it together. Ernie Banks was mediocre by the time I started to really care so I will pass on the obvious choice. Bill Buckner was GREAT when he was here. Loved his gritty style. A few bats around him and he may have topped this list. Andre Thornton was great-after he left the Cubs.

    Ultimately, your 2 choices are very fair. Do you side with longevity and greatness, or outstanding years over a shorter period of time? I go with Derek Lee. Until he hurt his wrist, he was the closest thing to Frank Thomas that I had seen in awhile. Nowhere to pitch him. He and Grace both had great gloves, hit for average, but Lee had power and drove in runs.

    I have to give a slight nod to Lee.


  4. Cookie52 says:

    Second Base. Easy, Sandberg. However, Manny Trillo was a very good ball player. Honorable mention for him.

    Third Base. This is a very difficult one. You would expect me to pick Santo because he is a HOFer and I knew him personally. Loved the guy. However, Bill Madlock was a tremendous hitter and pretty good glove. Typical of the Cubs, they didn’t want to pay him and ended up with Bobby Mercer at the end of his career. I’m going to give the nod to Madlock.

    BTW, a column on the Cubs giving guys away because they didn’t want to pay them would make a good column-Trillo, Bruce Sutter, Madlock, Kenny Holtzman. Alternatively, guys they gave away at bottom value rather than pondering if this was just an off year-Lee Smith, Fergie Jenkins.

  5. Cookie52 says:

    Shortstop. Easy, Castro. I am tired of the nit-picking this guy gets. There is a history of young shortstops who make a lot of errors early and settle down to be great shortstops. Castro has things you can’t teach, a great arm and very good range. Plus he can flat out hit. He is going to be fun to watch this decade!

    Right field and Center field. I am going to cheat a little here. Andre Dawson came up as a CF and played a handful of games there for the Cubs. So I am going to give Dawson CF with honorable mention going to Rick Monday. Rick did a lot more than just save a flag in LA. RF then goes to Sosa. However, if you ask me to choose, it would be Dawson over Sammy. Dawson did EVERYTHING well and played with an intelligence lacking in Sammy. Plus, The Hawk brought superior intensity to the field everyday.

    LF. Guys, Dave Kingman was a lot of fun to watch play. You stopped everything you were doing when he came up. Too bad he was an a-hole otherwise who hit for a low average. Honorable mention. The easy winner here is Billy Williams.


  6. Cookie52 says:

    Utility Guy. Always thought this should have been Brooke Kieschnick. He was a high first rounder who pitched and hit a ton in college. I envisioned him as an emergency arm and a back-up infielder. Alas, he was lousy at both. Bet you haven’t heard his name in years!

    I’ll go way back and take Paul Popovich. Utility infielder who would have started on a lot of teams but was blocked by Glenn Beckert.

    BTW, honorable mention in LF to both Alou and Rafael Palmeiro. Couldn’t believe when they traded Palmeiro. He hit everywhere he went-Witchita State, and the minors. He “only” drove in 65 runs his first year and the Cubs management lost patience with him rather than respect his track record.

  7. Cookie52 says:

    Starting Pitcher. I get to throw Fergie Jenkins into this mix. Fergie was a great pitcher with 6 straight 20 win seasons for the Cubs. He had an off year and in typical Cubs fashion, off to another team he went.

    Rick Ruschel and Kenny Holtzman also deserve as tip of the cap.

    Wood and Prior are 2 of my favorites. Wood had the best “stuff” and was a fierce competitor. Prior had great stuff but less than Wood. However, he was the better “pitcher.” The precision he had and the ability to keep a hitter off-balance, was the best I had seen in my life.

    However, for longevity and production, Jenkins deserves this honor.

  8. Cookie52 says:

    By the way, of the other guys you mentioned at starting pitcher, only Zambrano merits a mention. I know you are talking favorites, but only Zambrano touches on the elite category.

  9. Cookie52 says:

    Closer. This is actually a bright spot for the Cubs in my lifetime. The “Vulture,” Phil Regan in ’69. Bruce Suter and his split-finger fastball. Lee Smith and his intimidating presence/fastball. Carlos Marmol and the wicked things he does with a baseball.

    I give the nod to Suter. Watching the bottom drop out when he threw that pitch and the hitters looking absolutely helpless, was so much fun. Traded him for an unproven Leon Durham. Not enough for a lock for the HOF still in his prime.

  10. Lots of good stuff Uncle Bill. Us 21 year olds are still very young in the baseball world and our teams will most definitely change throughout the years

  11. Cookie52 says:

    I think I gave you my “best” players, which are still my favorites in many cases. One more list.

    1B-Bill Buckner-clutch
    CF-Corey Patterson. Had all the tools, was having an all-star season and tore up his knee. Unfulfilled potential-sad!
    LF-Billy Williams. I was always him or Santo in the backyard. When he came to the plate, he would spit in the air and take a practice swing at it. Sure my Mom loved me mimicking that!
    Utility-Reed Johnson
    Starting Pitcher-Mark Prior. I was SO excited with his 18-6. I thought we had a 1, 1A, and 1B with him, Wood, and Zambrano. If healthy, we probably did.
    Closer-Bruce Suter. Wish you young guys could have seen him pitch.

  12. I hope as I get older I’ll have guys to compare to Santo, Williams, Sandberg and Dawson to tell kids about

  13. Cookie52 says:

    Thanks for getting me to do this exercise. It was a blast writing this while listening to the ocean. I could get used to this.

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