Reviewing Jerry Dipoto’s trade deadline history

The trade deadline draws nigh and Angels fans are quite eager to see what it has in store for the Angels. Already trigger-happy GM Jerry Dipoto has pulled off two deals to improve the Angels’ chances at breaking their post-season drought, but it would seem that more might be in store. Rumors abound of the Angels making just one more minor deal or going full-blown Colletti and making a blockbuster trade or even two. The truth, as always, probably lies somewhere in between. With the rumor reporters spreading so much information, much of which is conflicting, there is no real way to tell what is going to happen. The best we can do is look to the past to see what Dipoto has done at previous deadlines to see if there might be a pattern to his machinations.

Jean Segura, Johnny Hellweg and Ariel Pena for Zack Greinke
This trade may live in infamy for quite awhile. Part of the reason is that Segura went on to have a stellar 2013 (though he has dropped off considerably), but the bigger reason is that the Angels so badly misread the free agent market with Greinke. You just don’t give up such a big package to rent a player unless you are going to at least try to re-sign him, but the Halos backed out of the Greinke bidding almost immediately because the bidding opened at a level that was already above the maximum they were willing to pay him.

OK, fine, we get it. The trade kind of sucked, but it is the only time that we’ve seen Dipoto operate as a buyer at the deadline. We could spend all day debating the wisdom of this trade, but the goal here is to learn from the trade. Specifically, what motivated him to do it?

Going all in on Greinke, at least from my perspective, was a move made by Dipoto not to just qualify for the playoffs, but rather to do some real damage when the Angels got there… which they kind of forgot to do. Oops. That unfortunate result aside, Dipoto threw down a “Flags Fly Forever” move to try and win the World Series. The Angels actually find themselves in that same position now. They are all but a lock to make the post-season, but a lot of people believe that their rotation isn’t quite qualified for a deep playoff run, especially if C.J. Wilson continues to stink up the joint. That certainly makes a run at David Price make a lot of sense.

But will Dipoto be gunshy after getting burned by Greinke? He certainly could be as that trade is oft levied against him when people talk about his job security. However, the real sin there was less what they gave up in the deal and more that they failed to re-sign Greinke. That won’t be quite the same problem for Price since he is under team control in 2015. That’s a lot more value for the Angels to get if they decide to go all-in and also a lot more time to convince Price to sign an extension. So, historically speaking, Dipoto seems the sort to at least try to land Price. The Angels still don’t look like they have the assets, but a lot of people said the same thing before the Greinke trade.

Frazier Hall for Barry Enright
I don’t even really know if this counts other than it was made in late-July of 2012. But, hey, a trade is a trade, right? This was simply a depth move for the Angels who were a bit shy on arms at this point. I only mention it because I can’t believe that the Angels gave up anything for Barry Enright. Frazier Hall is a non-prospect, but it does illustrate that Dipoto is willing to give up assets for even the most short-term and most marginal of gains. It also shows that Dipoto is not blind to the idea of roster depth, which is a good thing.

Alberto Callaspo for Grant Green
Honestly, I don’t see how this one applies to the current deadline situation. This was a straight up sell move to exchange an older asset for a younger asset. The only thing it really tells us is the value Dipoto placed on Green at the time and presumably still places on him. Since he might be a trade piece involved in talks with San Diego, that is worth something. Not much, but something.

Scott Downs for Cory Rasmus
This was quite the disappointing trade for Dipoto. It was hardly an egregious offense, but most expected the Angels to get more for Downs. To be fair, Downs was clearly no longer his old self, he was just old. But he had the reputation of a pretty good LOOGY and all the Angels got was a big league ready reliever with a 7th inning ceiling.

What does it mean to the Angels at this deadline though? Two things, actually. First, this is yet another example of Dipoto (or perhaps Dipoto’s underlings) liking to do business with certain clubs as this was the second trade the Angels have made with the Braves during JeDi’s tenure. Again, that’s not uncommon, but it is a factor worth considering. The more important aspect is that it shows that Dipoto may not have a great grasp on the way relievers are valued around the deadline. Here he got a pretty meager return for Downs. Fast forward a year and Dipoto paid a fair amount more to get Joe Thatcher. You could make a decent case that Thatcher is better than Downs, but not that much better. Yet Jerry gave up two prospects to get Thatcher. Neither guy is big league ready like Rasmus, but Zach Borenstein is a guy with a ceiling that could make the Angels regret moving him to rent a LOOGY. He’s far from a sure bet to realize that ceiling, but at least it is there whereas Rasmus has nothing resembling that kind of ceiling. Plus there is Joey Krehbiel, who probably has a similar ceiling to Rasmus, though he is a long way off from ever coming close to realizing it.

The improper valuing of relievers on the market and the willingness to rent and the willingness to trade for a guy with October in mind all adds up to Dipoto being more than willing to overpay for a high-end reliever. Or at least he was once, again, we aren’t working with a big sample here and market trends do change. Still, if I were the GM for the Padres, which I probably have a shot at given how many people have turned down the job, I’d be asking for a ton to give up Huston Street and I probably wouldn’t back off my demands.

Oh! I almost forgot. Dipoto did have a few months as the interim GM of the Arizona Diamondbacks. In that time, he engineered something of a fire sale, including the Dan Haren deal. He made a few smaller trades as well, none that I am familiar enough with to dare assess them. Even the Haren deal seems like a stretch since being an interim GM of a fire sale team is such a different dynamic than being a full-time GM of a contending team.

All in all, we don’t know anything for certain with what Dipoto will do just because he’s only been in the “deadline buyer” position once. We’ve seen that he is willing to make daring moves, take risks and overpay, but we don’t know if he learned from those experiences and course corrected. So, in summary, we don’t really know. Totally worth the 1200 words, right?

Garrett Wilson

About Garrett Wilson

Garrett Wilson is the founder and Supreme Overlord of and editor at The Outside Corner. He's an Ivy League graduate, but not from one of the impressive ones. You shouldn't make him angry. You wouldn't like him when he is angry.