The Two Ryan Dempster Trades, and How We'll Remember the Man

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The Two Ryan Dempster Trades, and How We’ll Remember the Man

Chicago Cubs

Unfortunately for the Chicago Cubs, baseball players are human beings.

That’s why, when you try to trade them, some tricky things can happen. So it was with now-former Chicago Cub starter Ryan Dempster. Yesterday, at the non-waiver trade deadline (with five minutes to spare), the Chicago Cubs sent Dempster to the Rangers for third base prospect Christian Villanueva, and pitching prospect Kyle Hendricks.

But that might not be the Dempster trade that you remember 10 years from now. You might, instead, remember the Dempster trade that didn’t happen.

That trade, of course, would have netted the Cubs 22-year-old pitching prospect Randall Delgado, a pitcher who might not have single-handedly taken the Cubs to the promised land, as hyperbolists like to joke. But he would have been a heck of an incredible return for two months of Ryan Dempster.

Circumstances dictated that the deal was not to be, and, unfortunately, also dictated that a comparable deal wasn’t to be found. Considering that no other team needed the Cubs to include cash in the deal quite like the Braves did, it’s understandable that the Cubs were never going to match, overall, the return they would have gotten from the Braves. Ultimately, they probably didn’t come all that close.

But that doesn’t mean they didn’t make a good deal, particularly when you consider that the failed Atlanta deal forced all sides to show their hands. When the dust settled, teams knew Dempster didn’t really want to go anywhere but L.A., knew that the Cubs very much wanted to move Dempster, and knew that Delgado-for-Dempster wasn’t just acceptable, it was dream-worthy.

From there, picking up a kid who was a fringe top 100 prospect going into the season (Villanueva) and an arm who was a top 30 prospect in a very good system (Hendricks) was a pretty good deal. If you’re like me, you would have been very happy with that return if you’d never heard the name Delgado mentioned days before.

Still, the trade wasn’t without its downsides.

The Cubs had hoped to deal Dempster far in advance of the deadline, if for no other reason than they wanted to create space between the time they were shopping Dempster and Garza. Why? It’s not an issue of effort or manpower. The Cubs can handle both things at once. Instead, it’s a simple issue of economics – perhaps the only one I still understand from a college class I only barely passed: if you have two commodities you’d like to sell, and the buying base for those commodities is the same, all things equal, you’d rather sell the two commodities at different times so that you can preserve scarcity. Sell ’em both at once, and the price will necessarily go down, because the market has more options. The two products will, in essence, be in competition with each other.

And that’s exactly what happened. We learned yesterday that the Cubs were deep in discussions with the Rangers, among other teams, about Matt Garza. But the Rangers explicitly chose Dempster because they preferred (1) his health situation, and (2) that he came with a lower price tag.

Had Dempster been traded a week or two ago to a team other than the Rangers, what happens yesterday with Garza? We’ll never know, but it’s always going to be fair to wonder.

Unfortunately, I can’t hang that on the Cubs’ front office. They got the deal they wanted for Dempster, and they got it more than a week ago. Why that deal fell through and who is to blame has been discussed ad nauseum since that time. I have learned enough since then, including some things I cannot share, to know that I’ll probably never pin the blame on anyone for how this played out. Just as I believe the Cubs’ front office did the best they could on the information they had, I believe the Braves did the best they could to wait on Dempster and then to force the issue, and I believe Dempster did the best he could to balance the Cubs’ interests and his own. Not only did Dempster have a right to ask the Cubs to keep trying to work something out with the Dodgers, he had good reasons to ask.

Theo Epstein discussed the failed trade with the media a few hours ago, and he confirmed – at least, in terms of what he was willing to say publicly – that events played out as we’ve suspected. The Braves were a team Dempster said he would consider, and the Cubs consummated that deal after alerting Dempster that it could be coming soon, and after the Braves game them a window to get Delgado. Dempster felt he needed a few additional days to think things over (and, let’s be honest, to hope the Dodgers came around), but the Braves imposed a deadline. Dempster wanted to wait until the last minute, on the hopes that the Cubs could work something out with the Dodgers. When it became clear – at the last minute – that it wasn’t going to be possible with L.A., Dempster relented, and took the deal with the Rangers.

It will be easy, in the years to come, to vilify Dempster by pointing to the vetoed Braves deal, and the ultimate Rangers deal, as evidence that Dempster screwed the Cubs. He didn’t go to L.A., after all, so why didn’t he just go to Atlanta? Why did he say back in June that he wanted to do right by the Cubs? Why did he tell the Cubs he would consider going to Atlanta? After they informed him that things were getting hot and heavy with the Braves, why didn’t he tell them he had serious reservations? Maybe, if he had a do-over, he would have done things differently. But I’m not sure I can, with good conscience, say that Dempster is the villain here. At worst, he had an ill-timed change of heart. At best, the Cubs were a bit too aggressive, and Dempster still tried to do right by the organization. The truth usually lies somewhere in the middle.

Unfortunately, when it comes to assigning “blame” for how things played out, I can lay it only at the feet of bad luck. The timing of things – the deadline, the other teams involved, personal issues involved, the Cubs’ desires involved, the reporting involved – conspired to form a perfectly bad sequence of events, and the Cubs paid the price in a reduced return on Ryan Dempster. It was no one’s fault, and the Cubs’ front office did the best they could to salvage a quality return for Dempster on July 31.

And let’s be clear on one thing: even if the Cubs had completed the Dempster-for-Delgado swap, we don’t know how the rest of the deadline plays out. Maybe the Cubs still can’t move Garza for a whopper (he is injured, after all). Maybe no other team wants Maholm nearly as much as the Braves did, and the Cubs can’t move him, either. Or maybe they move him for substantially less than Arodys Vizcaino, who, when healthy, was preferred by many prospect gurus to Delgado.

All we know for certain is that Ryan Dempster allowed himself to be traded, and so ended his days in Chicago.

Maybe you didn’t think he was funny. Maybe you hated his Harry Caray impression (which was actually an impression of Will Farrell doing a Harry Caray impression). Maybe you didn’t like his zingers in the media. But at least the guy was interesting.

Dempster gave his fair share of stock answers, and did a lot of the standard things you expect of a big league player, but he also occasionally surprised. As much as baseball is about the performance of the players on the field, personally, I like to see a little bit of who they are off the field. Dempster showed us a little bit of that, and I thank him.

On the field, it’s impossible not to recognize his accomplishments with the Cubs. Dempster was the most consistently good starting pitcher the Cubs have had since 2008. Before that, he was a decent reliever.

Remember when the Cubs converted him into a closer? Remember how that seemed like a risky idea? Remember how he dominated as a closer? Well, for that first year, anyway.

Remember when the Cubs converted him back into a starter? Remember how that seemed like an absurdly risky idea? Remember how he dominated as a starter?

There are good things to remember about Dempster’s time with the Cubs. Will the failed Braves trade, and resulting Rangers trade, always be a part of the story? Yes. Will there always be a little sting, and a little frustration when calling to memory the days leading up to his trade? Yes. But I’m going to do my best to remember the good, as well.

But it wouldn’t hurt if Randall Delgado fails to make it back to the big leagues.

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Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.