Jerry Dipoto: a successful GM that failed BIG

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Jerry Dipoto‘s embattled tenure in Anaheim has come to a premature end. Dipoto leaves behind a franchise now embroiled in turmoil but also a legacy which history will likely look back kindly on. His reign accomplished most everything that he wanted it to in terms of building a long-term foundation for the ballclub, but he achieved that success and ultimately caused his own demise because the failures he had were very big failures.

If you look at what the Jerry Dipoto regime did during the three and a half years that it was in place, it is hard to be upset with what the regime accomplished. Jerry inherited a barren farm system, no international scouting presence, a roster that was old and full of holes, and a number of bad contracts.

By the time Jerry freaked out and quit, he had started the farm system’s turnaround. While still not a good farm system, it is finally moving in the right direction. Part of the reason for that is that Dipoto was able to rebuild their scandal-ravaged international scouting department.

The Halos also now boast a more complete roster that has been infused with young talent like Kole Calhoun, Carlos Perez, Kyle Kubitza, Garrett Richards, Hector Santiago, Matt Shoemaker Andrew Heaney and Trevor Gott with the likes of Tyler Skaggs, Sean Newcomb and Nick Tropeano waiting in the wings. The bullpen was an utter disaster when Dipoto first came aboard, but Jerry’s wheeling and dealing has created a relief corps that is solid and occasionally capable of dominance. The roster isn’t without flaws, like left field and the DH slot, but Dipoto has at least built out some organizational depth to try and address those flaws before being forced to turn to the trade market.

The Angels also seemed headed straight for payroll hell after Dipoto, at Arte Moreno’s urging, signed Albert Pujols. However, Jerry was able to sign Erick Aybar and Howie Kendrick to team-friendly extensions, trade for and then subsequently re-sign Chris Iannetta at a reasonable price and, above all else, lock Mike Trout into a fair extension before he even hit arbitration. The financial flexibility of the team remains limited, but Dipoto has at least carved out enough space under the luxury tax for the remnants of the front office to swing a big deal at the coming deadline.

We could go on in more detail, but the basic takeaway is that the Angels are in better shape than they were when Dipoto was first hired. That’s really all you can ask for from a GM. Well, that and winning some games. On that front, Jerry’s results were more mixed.

Jerry delivered two winning seasons (and possibly a third if things hold up this year) but just one playoff appearance that culminated in an embarrassing sweep. That’s not a bad set of results, but it was less than what was expected of the Halos. But what really did Dipoto in the eyes of many fans, and likely Arte Moreno as well, was that sprinkled throughout Dipoto’s overall success were some very big failures.

The thing about these failures is that they all (well, almost all) came from the same sound process that helped him achieve that overall success. He took all the right kind of risks and sought value in all the right places, but when those risks bit him in the butt or the value vanished, it was in a worst case scenario kind of way.

His first arguable whiff was surrendering a prized package of prospects for Zack Greinke. It was the ultimate in “win now” moves, something Dipoto never shied from, possible at Moreno’s behest. Greinke was terrific for the Angels and despite a strong rookie campaign from Jean Segura, the prospects he gave up haven’t really been missed.

What was missed, however, was Greinke, who bolted after the season when the Angels decided the bidding had gotten to expensive. This is not a decision that Angel fans remember fondly, especially since the money meant for Greinke ended up being spent on the ill-fated Josh Hamilton contract. Moreno’s meddling int he situation absolves Dipoto of some blame, but for the next several years, there won’t be an Angel fan that doesn’t rue the day Dipoto had Greinke and let him slip away.

He followed that up by dumping Ervin Santana that same offseason despite the team’s desperate need for rotation help. Santana was coming off a disastrous season and the team doctors were deeply concerned over the health of his elbow. Cutting bait on Santana seemed like the only sensible move. Only Ervin landed with the Royals, had a career season and has yet to see his elbow implode. It was the Dipoto regime in a nutshell, right process but the wrong result.

But if there is one lasting image that will forever dog Dipoto, it is this one.

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In a matter of weeks, Dipoto made four well-meaning but doomed transactions. He signed Sean Burnett to address the lack of left-handed relievers in the beleaguered Angels bullpen. Burnett had a great track record and signed for a reasonable price. There was nothing to dislike about the deal from a process and logic standpoint… right up until the point Burnett’s arm stopped working. Even with his injury history, Dipoto could’ve never seen that coming.

He probably didn’t see the arm problems that plagued Ryan Madson coming either. In a day and age where Tommy John surgery has a virtually 100% recovery rate, Dipoto managed to sign the one guy who didn’t recover. It didn’t cost the Angels much money, just some embarrassment at a prized free agent signing never actually taking the mound for the team.

In Tommy Hanson, Dipoto knew he was taking a risk. Hanson’s shoulder problems were well-documented, but he was willing to gamble that the young, team-controlled arm that was only two years removed from looking like a Cy Young candidate could overcome those issues. The price he paid was a young, promising reliever but with injury concerns of his own. While Jordan Walden has found success and the DL since being dealt, Hanson imploded immediately. There was no mechanical fix that could save him. Dipoto’s gamble came up snake eyes.

And then there is Joe Blanton. At a price of $15 million over two years, Blanton hardly broke the bank for the Angels, but he nearly broke their spirit. He was never a frontline starter, but he had the credentials of a workhorse veteran that could be counted on to hold down the #5 starter spot and eat innings without hurting the team. Only he didn’t. The underwhelming but consistent Blanton shouldn’t have been a risk at all, yet he ended up turning in one of the worst starting pitcher performances in decades and didn’t even finish the supposedly pain-free two-year contract.

Subsequent moves on seemingly little consequence found a way to blow up in his face as well. Trading the increasingly expensive Kevin Jepsen and his notoriously volatile performance for the steady bat of Matt Joyce should’ve been a no-brainer. Like the Walden-Hanson deal, anytime you can deal a middle reliever for a regular at a more important position, you have to do it. Then Joyce had to go and completely crater upon arriving in Anaheim.

None of these moves alone would’ve been career-defining for a GM, but add them all together and you can see why to some observers the stench of failure has followed Dipoto despite him pulling off several heists like the trade of Trumbo for Santiago and Skaggs or plucking Ernesto Frieri out of obscurity and then flipping him for Jason Grilli right when he started to go bad.

Dipoto took the calculated risks that so many GMs are often too afraid to take for fear of their own job security. If they had worked out just a bit better, Jerry might still have his job. Instead, he hit a run of bad luck and paid the ultimate price for it.

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