Playing Catch: 10 Biggest Trades in Rockies History

We’re kicking off a new weekly column where one of our editors, Isaac Marks, tosses around an idea with one of our staff writers. For the inaugural edition of Playing Catch, Logan Bannon joins to discuss the ten biggest trades ever made by the Rockies.

Top 10 Trades in Rockies History

Isaac Marks: So we’ve both made our lists of biggest trades. What criteria did you use to rank them?

Logan Bannon: I went through multiple layers. First, I went through the master list and cut out the trades where I never heard of anyone in the transaction. Let’s be real. I’ve followed Rockies history enough to where if I don’t know who you are, you don’t matter and your trade is irrelevant.

This left maybe half to 2/3 of the trades left. My second round was me cutting out the trades of guys who I have heard of but before they mattered. I could write a whole rant about the “what if” players that we have traded away (Brad Ausmus, Jermaine Dye, Chone Figgins to name a few), but I can’t say they were impactful because they weren’t big-time players when the trade happened. In other words, I tried to separate what could have been from what it was at the time. We can sit here and rack our brains about trading Figgins when he was in Double A, but did that really impact the major league team at all?

From there, it got really tough. I basically had to step back and become a fan. What trade changed the most? Being the Rockies, these mostly ended up being sell-offs of our best players (Ubaldo, Tulo, Holliday) but also acquisitions of guys that ended up being game-changers (Fuentes, De La Rosa). I realize this is a bit of a double standard since these were the same types of “what if” trades that I discounted. It’s my list and I do what I want. Sue me.

I also took the timing into account. Trading away a good player in 1999 didn’t make a huge difference because we sucked either way. Trading Holliday when we still looked like contenders seemed like a bigger deal than trading Castilla at the back-end of the Bombers era.

Finally, except for Fuentes and Ubaldo (arguably our best starter and reliever ever), I discounted pitching trades. There were simply too many. Every reliever in Rockies history was apparently acquired via trade. I am not going to sit here and rank all of our relievers. They’re very interchangeable. They’re out.

The same thing, to a lesser extent, with starters.

As you can see, I really retreated to the research lab to do what amounted to cutting and pasting a word document. What did you do?

IM: I started the same way. Eliminated the guys I couldn’t remember, didn’t give them a second thought. I then made two lists; biggest trades and best trades, ranking them by shock factor/players given up or received and best value, respectively. Since this is the Biggest Trades in Rockies History list, I went with the first list.

I picked out the fifteen top trades in no particular order and then moved them around from there. I also discounted “what if” players because they didn’t make much of an impact for the team and, let’s be honest, many of those trades would be on a Worst Trades list instead.

The biggest difference between our lists was that I didn’t count timing. I took them at face value.

Let’s jump right in; what was your first trade?

LB: The biggest trade in Rockies history is, in my eyes, is the Holliday trade. There are probably 3 trades that could realistically be in contention for #1 depending on your perspective. I chose Holliday because to me, it seemed like the end of the Rocktober Rockies and the start of the next generation. Trading your best player from the 2007 team for one of the best players on the 2009 team seems like a huge deal. Plus, we got Huston Street out of it, which was a good piece to extend our window a little bit.

Not to mention, it also seems like a key battle in the ongoing War on Boras.

IM: Yeah I went with the Holliday trade as well. We basically matched Holliday’s output with CarGo’s future and added a closer that helped with the 2009 playoff run. The trade definitely made the team better in the long run and set the team up with two perennial All-Stars, when healthy. Key part there.

The War on Boras is a never-ending battle, my friend.

Trade number two on my list was the Tulo trade. Jeff Bridich finally made the hard call and started to “rebuild”. Or, at least, so we thought. The guys the Rockies got back have looked good in very short stints but I still have high hopes. What’s your number two?

Apr 29, 2015; Phoenix, AZ, USA; Colorado Rockies shortstop Troy Tulowitzki (2) looks on during the first inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Matt Kartozian-USA TODAY Sports /

LB: The war always seems to end with our best player leaving. I think that means that we are losing, right?

My second trade was the Tulo trade as well. I don’t think there is much arguing with either of these first two. Obviously we don’t know the full outcome yet with the value on our side still not doing anything in the bigs, but like you said, it seemed to be a sign that we are starting over. Then we went and signed Mark Reynolds and Gerardo Parra. Go figure. Anyway, it’s hard to argue that trading the face of the franchise for the last 5 years should be anywhere but the top end of this list.

We got the first two spots out of the way. Now I think things will get interesting…

For number three, my guess is that you have Ubaldo. I don’t like that one at 3. I’m going to take you back to 2002. We traded a washed-up Mike Hampton and a young Juan Pierre to the Marlins for Preston Wilson, Charles Johnson, and a couple of guys who are forgettable. I picked this trade for a few reasons. First of all, Juan Pierre was the prototype of a leadoff hitter for like a decade after we traded him. He was already good when we got rid of him, but he sustained it and could have been our guy at the top of the order forever. Getting rid of Mike Hampton was basically admitting that the signing didn’t work out. We still haven’t recovered from it. We are too scared to give anything near that amount of money to another pitcher.

Editor’s Note: In the linked article above, the NY Times author called Colorado “The Bermuda Triangle for pitching”. Nice.

On the other side of that, we got back our starting center fielder and catcher. People always seem to forget, Preston Wilson was one of our 2 or 3 best players for a year and a half. I picked it mainly because of who we gave up, but it’s not like we didn’t get anything back.

More from Rox Pile

IM: Yeah I have the Ubaldo trade at three. It got a top three ranking because of the drama Ubaldo caused throughout that tumultuous 2011 season. The amount of grief that entire situation caused that season was unbelievable. I was so mad that I wrote a 2500-word rant on Facebook about how freaking pissed I was and how it was going to bite us down the road. Well, Ubaldo hasn’t been as good as I thought he would be, but I was right about the return. Not a single player from that trade is in the organization anymore.

I just don’t consider a top player on our terrible 2003 team as a win…

LB: Yeah that drama got ridiculous. Everyone lost from that one. I have Ubaldo’s trade at #4 cause of all that. Everything from that entire thing was stupid and I hate it. But hey, at least we didn’t end up paying him.

I agree. Like I said though, giving up Mike Hampton was a huge deal in my eyes! He was supposed to be our first legit pitcher. The trade was us throwing in the towel.

IM: My fourth biggest trade in Rockies history is a little nostalgic; the Larry Walker trade to the Cardinals. I didn’t understand why it happened until I was business-savvy enough, but I was NOT happy. This got a personal boost in the rankings for an otherwise small impact return.

One of the few good choices Dan O’Dowd made (BURN)

More from Colorado Rockies All-Time Lists

LB: Yeah I have that one further down my list. Definitely a lot of sentiment there. I always felt like Larry had a lot more in the tank when we traded him. When I looked at it for our podcast the other day, it didn’t really seem that way anymore. In the end, I didn’t feel right ranking it higher because we traded a dude in the twilight of his career for a few guys that didn’t matter. If we made that trade like 2 years earlier, it would probably be up here for me.

Did you see the other day, Dan O’Dowd said of all the trades he made, his biggest regret was trading a minor league Chone Figgins? Really? That’s the one that keeps you up at night?

IM: Looking back at these rankings, this pick will likely be my Dan O’Dowd moment. Oh well…

THAT WAS MY FIRST THOUGHT. Of all people you regret giving up its Chone Figgins?

Anyway, this is turning into our podcast on paper and I like it, but let’s stick to the schedule for once. What’s your five?

LB: I’ll go back to one of our first trades ever. We got Dante Bichette from Milwaukee for some guy named Kevin Reimer. This got the ball rolling. Dante to the Bombers was like Ringo to the Beatles. This trade set the tone for the early Rockies, and baby Logan is forever grateful that they brought in one of his idols.

IM: Good choice, it’s coming up on my list. I went with the 2001 Jeff Cirillo trade. We got back Brian Fuentes, Jose Paniagua and Denny Stark. Man, Denny Stark….Maybe it’s my 9-year-old memories, but wasn’t Cirillo a big deal to give away?

Plus, Fuentes was a nice addition. Apparently a “good return” in my book is a reliever.

LB: Ahh yes. Denny Stark, the key piece to that trade. What a professional.

Yeah Jeff Cirillo was super good. Didn’t hit mad dingers, but had a great average and a lot of RBIs. It’s funny you say that after knocking my Preston Wilson comment. They seemed to be pretty similar levels in terms of skill. Jerk.

When most of our trades have a list of minor leaguers who are never heard from again, I’ll consider Brian Fuentes a good return 8 days a week. I also have that one coming up later as well.

Moving on to the lower half of the list, what do you have for #6?

IM: True, Cirillo only played two seasons in a Rockies uniform like Preston but one of those was an All-Star season, so that’s major points.

Remember Jason Jennings? We traded him with Miguel Ascensio (?) for Jason Hirsh, Taylor Buchholz and Willy Taveras.

LB: Yeah I remember Jason Jennings. Rookie of the Year. Future Cy Young winner. You could say I was hyped about him.

IM: And he hit a home run in his major league debut to go with a complete game

LB: What a solid trade though. I loved Willy Taveras when he was here. Sooo fast. He probably hit .300 at some point, and I swear it was solely based on bunt hits.

IM: Honestly this should be higher. We sold high on Jennings and got three major contributors for a few years.

Also, Jason Hirsh was solid before he broke his leg.

What’s your six?

LB: Yeah definitely got the most out of a guy who didn’t really do anything in Houston. I still remember Jason Hirsh through probably his best game in Colorado after getting hit with a comebacker. He went all Greg Jennings, sat people down after he broke his leg. Buchholz was a forgotten guy too. I think he was a TJ guy, but he was good for a year or two. Probably one of the bigger “win” trades in Rockies history.

My #6 was trading reliever Ramon Ramirez to the Royals for a player to be named later who ended up being Jorge De La Rosa. I know what I said about trading for people before they were big, but I’m making an exception here. George of the Rose ended up being a huge piece for us over the last decade, and I can’t leave that off the list.

IM: That’s my seven! This is by far O’Dowd’s shrewdest move of his tenure as GM. De La Rosa has continued to be an anchor for a sinking ship recently, but has produced some of the best pitching seasons we’ve seen in recent memory AT Coors Field. Something that’ very hard to do. Remember when George Frazier called him George on broadcasts? Ha.

LB: Easily. Sneaky good deal. Good work, Dealin’ Dan. Try to forget I ever said that.

I think Frazier was referring to himself. I don’t remember the specific time you are referring to, but I remember the thousands of times he talked about his own playing days. There’s no need to have the audio on during a game. It’s just Huey and Frazier talking about themselves for 3 hours.

Sorry if you sense the bitterness. Back to the focus. What trades do you have left that haven’t already been talked about? I only have one left that I have ranked at #9.

IM: Already forgotten.

Frazier definitely couldn’t pronounce “Jorge” so he just called him George. The fact that it was allowed to go on for as long as it did was both hilarious and terrifying.

I’ve got two; the Bichette trade was my 8. At nine I have the Ian Stewart/DJ LeMahieu trade.

I ranked it this low because of the lack of fanfare surrounding it. It was one of those trades that the Rockies didn’t want people to know about because they didn’t want to give up on Stewart. He could hit the ball so freaking far.

The best part is that DJ LeMahieu is by far the best player out of the four involved. Casey Weathers has made a few appearances here and there and Tyler Colvin is in Triple-A purgatory.

LB: Yeah, it’s funny how that worked out. I have that trade as my number 9 as well. I remember when it happened, I was so disappointed that we got to the point where we gave up on Stewart. I thought he would be our cleanup hitter for a decade. Then when we gave up on him, I said, “well, at least Tyler Colvin is really good.”

Wrong again.

I knew nothing about LeMahieu. I didn’t think he was anything special. Now here we are.

Overall, my bottom 4 round out like this:
7. Jennings for Taveras/Buchholz/Hirsh
8. Cirillo for Fuentes/Stark
9. Stewart for LeMahieu
10. Walker to the Cardinals

Casey Weathers was an injury casualty, if I remember correctly. Stewart got drunk and tweeted out how much he hated the Cubs. He then got traded for nothing. That’s the worst way to sour your reputation outside of when Shawn Chacon choked out his GM in Houston.

IM: Ha. Former Rockies doing crazy things to end their careers, like Miguel Olivo biting a guy’s ear off Mike Tyson-style.

My last trade was from the Summer of 2009 *In Summer of 69 tune* involving one Connor Graham and the legend, Rafael Betancourt.

Keeping in line with my apparent love for late-inning relievers.

LB: Good call. “The Human Rain Delay” was definitely a big pickup.

IM: Now there’s two trades on here that still have a chance to make this list in the future; Chris Iannetta to the Angels for Tyler Chatwood and Dexter Fowler to the Astros for Brandon Barnes and Jordan Lyles. Care to comment?

LB: These trades actually seem fairly similar to me and I would say the same thing to both: It depends how the starting pitchers turn out. We both had De La Rosa on this list because he ended up being a solid pitcher for us for a long time. If either Lyles or Chatwood end up sticking around as a long-term rotation piece, that pushes their trade up this list, especially since we gave up significant major league pieces to get them. If neither of them works out, I throw them in the same category as the Hammel and Guthrie acquisitions. Forgettable short-term rotation trades.

IM: The Guthrie Era was darker than the Kyle Kendrick Era, so that’s not even close to Chatwood and Lyles. If one of them can stay on the mound for a full season, they’re both talented enough to make a difference. Or maybe we should just combine them into a superhuman and hope that their combined stamina resists the urge to be injured.

LB: Fair point. I suppose not playing at all is better than what Guthrie or Kendrick did.

Maybe if they have two UCLs, their elbows wont rip apart like wet newspaper. Anybody who can throw 200 innings in a season and keep an ERA under 4 deserves a statue out on Blake Street. Tydan Lywood could do just that.

IM: Now that we’re going into human splicing I think it’s a good time to end…

LB: If you insist. I’m just getting started though. I’ll get back to you if I have any other ideas.

Next: Christian Friedrich is No Longer a Rockie

Former Colorado Rockies First Round draft pick Christian Friedrich was claimed off of waivers by the Los Angeles Angels following his designation for assignment on January 28th. Friedrich, the casualty from the Corey Dickerson/Jake McGee trade from the 40-man roster, has posted a career ERA of 5.81 over 167.1 innings, including 19 starts.

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