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Courting Controversy: Jerry Dipoto's Boldest Moves

Hired by Arte Moreno in October 2011, Jerry Dipoto wasted no time implementing his ideas. Let's look back at some of his more noteworthy moves.

Fix that cowlick, Jer, you've got job interviews to schedule.
Fix that cowlick, Jer, you've got job interviews to schedule.
Kirby Lee-USA TODAY Sports

1. Bye bye, Jeff! And safe travels, Mickey!

Within six months of assuming the helm of the Angels' front office, Jerry Dipoto traded Jeff Mathis to the Blue Jays for Brad Mills and axed hitting coach Mickey Hatcher after a disappointing start to the 2012 season. These moves were a direct message to manager Mike Scioscia: I run this team, and I decide which toys you get to use. It was the Hatcher canning, though, that irked Scioscia the most. A guy normally known for his close-to-the-vest strategy of media interaction, Scioscia has been an open book (stuck on the same page, ironically) regarding the topic of his friend and former teammate getting the ax. Just a couple days ago, in the midst of the front office shakeup, Scioscia brought it up:

"The one real issue … was when they let Mickey go," Scioscia said. "But we moved past that. Moved way past that."

Yeah, and if you believe that was the only real issue during Dipoto's three-and-a-half years with the Angels, I have a bridge from Philadelphia to Los Angeles to sell you. I also have a hard time believing they've moved "way past that". It was three years ago, Sosh, and, as of July 1, 2015, you won. Get over it.

2. Let's sign Albert Pujols and C.J. Wilson. ON THE SAME DAY!

If the first move on this list was a message to Mike Scioscia and the world of Angels baseball, this move was a message to the entire world: We're signing the best free-agent pitcher on the market and, oh yeah, we're going to sign the best player of the last 10 years. Get ready, world, here come the Angels.

Now, the Pujols signing was reportedly 99% Arte Moreno, and this is where Dipoto's tenure as Angels GM starts to get interesting, for he quickly realized that he wasn't the main man when it came to personnel decisions. Arte negotiated with Albert, Arte wooed Albert, Arte included a 10-year personal services clause in an already ridiculously long contract, Arte gave him almost a quarter-billion dollars. But C.J. Wilson was Dipoto's call. As far as I'm concerned, Arte Moreno doesn't even know why pitchers are such a big deal, so I think it's fair to say that Dipoto pulled the trigger on this one.

3. We need pitching? Get me Hambone!

Whoo, boy, do I need to elaborate? We all know how it ended. Oh, man, do we know how it ended. And we all know how it middled. Oh, man, do we know how disappointing Josh Hamilton's on-field play and taking-him-off-the-field injuries were. But how did this story begin?

Following a trade deadline move in 2012, where the Angels shipped off the farm in exchange for the services of Zack Greinke, the team made it known the following offseason that they probably weren't going to be very involved in the bidding for the mercurial, yet incredibly gifted, hurler. Reports were that Greinke wanted the maximum amount of money. Reports were later confirmed. So, okay, that's fine. It happens. Many Angels fans questioned trading as much as the Angels did for thirteen starts of Zack Greinke not only when the trade occurred, but also after Greinke signed with the Dodgers. Why would you  give up so much if you weren't sure you could re-sign him in the offseason? Again, it happens. It's disappointing, but it happens. And, I mean, that money! $150M for six years of a pitcher? No way. The Angels needed pitching desperately, but that kind of money for a guy who plays, at most, 32 games a year is just ridiculous, many of us rationalized. Let's set our sights on a more reasonable alternative, like Anibal Sanchez. Good idea, right?

So, on December 14, 2012, the news came down that the Angels signed Josh Hamilton for five years and $125M. Huh? An outfielder added to the talented group of outfielders the Angels already employed? Many of us wondered if he could pitch. He couldn't. And he could barely hit. Or field. Or stay on the field.

Remember how Dipoto got a wake-up call about who really made the personnel decisions when Albert was signed? Well, the Hamilton signing may have been another reminder, just in case Dipoto wasn't sure. To be fair, opinions are still divided as to how much influence Arte wielded over this signing. We've had commenters on this very site offer some insider info that suggests it was a Dipoto signing. Some reports point to Arte. I'm inclined to agree with the latter. After all, it's a classic Arte move. Who cares about pitching when you can sign a guy who hits dingers and got an MVP Award once? And the added benefit of "sticking it" to your division rival? That's good stuff.

4. The Dipoto Four

Gross. One of Dipoto's big-time misses. And he's had his share too. I don't want this article to come off as too Dipoto-rific. As a GM, like every GM ever, Jerry Dipoto took some risks and whiffed on several of them. The Dipoto Four, though? Ugh. Just a bad idea, pretty much from the start. Being the Pollyanna that I am, I thought, "Hey, Sean Burnett is a great reliever, Tommy Hanson is totally going to be a diamond in the dumpster, Joe Blanton Ks a ton of guys, DURR, and Ryan Madson was good before he went down with an ELBOW INJURY."

A family tragedy, way too many dingers, an injury and one complete no-show later, the Dipoto Four had spoken: "We stink."

Now, to be fair to Jerry, these moves were necessitated by Arte's meddling. Hamstrung by a somewhat arbitrarily imposed salary cap in response to the league's luxury tax threshold, Dipoto had to go dumpster diving. However, in my experience from what I've heard, dumpster diving usually results in some meat on the T-bone from last night's dinner.

5. You may like their hustle, but I got a job to do.

This is truly a mixed bag. Getting rid of fan favorites is always a tough way to go as a GM. But that's a GM's job, to make the hard moves behind the scenes so that the play on the stage goes off without a hitch. And, for the most part, the play has gone on. In return for three franchise faves, the Angels received David Freese, Fernando Salas, Hector Santiago, Tyler Skaggs and Andrew Heaney. On the negative side of things are David Freese and Fernando Salas, plus the fact that Randal Grichuk, one of the only power-hitting prospects the Angels still had on the farm, was sent out alongside Peter Bourjos. The outfield depth took a serious, near-fatal hit, especially when you consider the fact that Matt Joyce is playing in left field as I write this very piece. And we got a perfectly average third-baseman and a completely mediocre middle relief pitcher in return.

However, turning a high-strikeout, low-OBP masher into Hector Santiago (our current staff ace, as unbelievable as it is to write that) and Tyler Skaggs, an extremely promising young lefty with a devastating bender, was a clear win for Jerry Dipoto and the Angels. Don't get me wrong, I love Mark Trumbo. His work ethic, his demeanor and those absolute bombs were so easy to cheer, but the return was too good to deny.

Now, the Kendrick-Heaney trade is, I think, a positive one all the way around. One year of Howie Kendrick for six years of a young, cost-controlled and excellent pitcher is a pretty nice move. But I do miss Howie. I loved cheering for him and I loved the opposite-field doubles he would rope. And he sure could flash the leather at the keystone. Perhaps because the 2015 Angels are so disappointing on the offensive side of things, this trade is a harder one to score a clear win. If Heaney keeps turning in starts like the ones he's thrown so far, though? We'll all be asking, "Howie who?" sooner than later.

6. Huston, we have a bullpen.

The most glaring problem with the 2014 Angels was the bullpen. "Was" being the operative word. As the 2014 trade deadline loomed, Jerry Dipoto pulled off a six-player deal with the San Diego Padres. The Angels got Official Closer Huston Street and prospect Trevor Gott, a hard-throwing reliever, in exchange for two of their remaining infielder prospects, Taylor Lindsay and Jose Rondon, hard-throwing reliever R.J. Alvarez, and low-minors pitcher Elliot Morris. Huston Street has logged quite a few innings for the Angels and done very well so far, impressing Angels' brass enough to earn a three-year contract extension. And Trevor Gott has looked magnificent in the very small sample size of innings he's logged this year.

Of the four players we gave up, only R.J. Alvarez has seen major-league action, with the Oakland A's. He was part of the package that Oakland received in the Derek Norris trade before the 2015 season, but he hasn't done a whole lot for the A's, pitching to a 13.00 ERA over nine innings. SSS caveat definitely applies; this kid is super-talented and I wouldn't be surprised if he makes us regret the trade in a few years' time. Taylor Lindsay, Jose Rondon and Elliot Morris are all having rough 2015 campaigns, but they're young, so who knows? As of the writing of this article, this bold move is a win for the Angels. In two or three years, though? I'm not so sure.

7. It's me or him. Who you gonna choose?

Talk about being forced into a decision by Arte's meddling. After three-and-a-half years of win-now moves, modest farm-building, almost no presence on the international market and a, ahem, tense relationship with his on-field counterpart, Dipoto went to Arte Moreno with an ultimatum: Get a new manager, or get a new GM. Well, Arte chose Mike Scioscia. To be fair, Arte tried to broker a peace between Scioscia and Dipoto, but Dipoto stuck to his guns and cleaned out his holsters desk. If a man ain't got principles, he ain't got nothin', I suppose.

This bold move, however, came on the heels of doing something rather reckless: dragging the players into the drama. Calling out the coaches, whether they were at fault or not, in front of the players was not a good move, nor was the decision to send scouting reports directly to the them.

Jerry Dipoto. Bold 'til the end.