Jerry Dipoto is a man with a vision. He’s among the most detail oriented executives in all of baseball. It’s generally how his mind works, he’s analytical and calculating. Some call it diligence, others, obsessive. He’s also proven to be a risk-taker, which can be a very good thing or bad thing in this business. Before becoming the General Manager of the Los Angeles Angels, he was the interim GM of the Arizona Diamondbacks, filling in until Kevin Towers would be hired. At the time he had an underperforming ace in Dan Haren on the trading block. Dipoto would later be blasted by the media for not trading Dan Haren to the New York Yankees when they were offering a package of Jesus Montero, Ivan Nova and more.

He instead traded Haren to his future team, the Los Angeles Angels in return for relatively unknown LHP prospects Tyler Skaggs and Pat Corbin and inexpensive inning eater LHP Joe Saunders. The deal was described as a heist for the Angels. Three years later however, it appears Dipoto knew what he was doing. Nova is a backend starter and Montero is a weaker hitting DH, Tyler Skaggs would go on to post an ERA under three in the minors with a high K/9, emerge as a Top 15 prospect and make it to the majors by age 20. Pat Corbin would climb the ladder steadily and make it to the majors as a 22 year old at the backend of the D-Backs rotation. Saunders would provide the D-Backs with two full years in the rotation and an ERA in the low 4’s/high 3’s.

But the controversial moves didn’t end with his tenure in Arizona. When Jerry Dipoto was given the reigns to the Los Angeles Angels before the 2012 season, he inherited a minor league system flushed with Top 100 prospects and a team coming off an 86 win season. Still, he felt a complete makeover as needed. He saw an over-performing team and an over-rated farm system. Dipoto replaced the entire front office of the Angels, fired most minor league scouts, coaches and coordinators, hired new ones, and even replaced a major league pitching coach that had been with the Angels since Dipoto was still a pitcher in the Rockies organization.

But it appears Dipoto’s moves were not unwarranted. GM Tony Reagins and his front office were developing a bad reputation in the league and were responsible for debacles such as the Vernon Wells and Scott Kazmir trades. But after Dipoto’s house-cleaning, perception of the Angels changed. You’d think this would take a wildly successful 2012 season and a farm that’s the envy of every team in baseball, but quite the contrary. The Angels missed the playoffs again last season and now have a farm system that very well could be ranked dead last in all of Major League Baseball. So how did they become regarded as one of baseball’s new powerhouses in an increasingly Western shifting power structure?

Simple really, it took risk, and a lot of future money.

November 30, 2011 – Angels trade 76th ranked prospect Tyler Chatwood for catcher Chris Iannetta. Iannetta had one year left on his contract and was coming off a season in which he hit .238 playing for the Rockies at Coors Field. Chatwood was coming off a season in which he made it to the major leagues at the tender age of 20.

December 7, 2011 – The Angels sign a TV deal with Fox Sports that will pay the team upwards of $3 billion over 20 years. That’s a lot of money, but the new TV deal does not kick in until 2016. So the Angels would probably best be served not spending this money for another five years.

December 8, 2011 – The Angels sign 32-year-old Albert Pujols to a ten-year, $254 million contract with an additional 10 years of service following his playing career. Never mind on the “wait five years before spending the money” plan. In order to afford such a deal, the Angels backloaded Pujols’ contract so he won’t get expensive for quite a few years.

December 8, 2011 – The Angels sign 30-year-old LHP C.J. Wilson to five-year $75 million contract. Wilson, formerly the ace of the rival Texas Rangers returns home to Southern California. Despite being 30 years old, Dipoto believes that Wilson’s years as a reliever significantly cut down the mileage on his arm and is confident Wilson will remain productive for the entirety of the contract. Once again, Dipoto opts to backload a contract in an effort to keep payroll down until the TV deal kick in.

May 3, 2012 – The Angels acquire reliever Ernesto Frieri from the San Diego Padres in return for 2B/SS Alexi Amarista and RHP Donn Roach. Frieri was a HR prone middle reliever, so I imagine the Padres were surprised to see anyone so interested in such a replaceable piece. Frieri went on to seize the Angels ninth inning role and posted some eye-popping numbers (54 IP, 80 K, 2.32 ERA).

The following season (2012), as many of us realize, the Angels fell short of their goal, winning 89 games and failing to reach the playoffs. The season was defined by the emergence of Mike Trout as the greatest player on the planet and a complete collapse of the Angels rotation, with awful seasons from Dan Haren and Ervin Santana hastening that collapse. To make matters more complicated, Haren and Santana were former all-stars with expensive options, the bullpen was left in shambles and Torii Hunter was set to hit free agency. Midseason acquisition Zack Grienke cost the Angels three of their top prospects and appeared to be headed for a record contract, despite not being a record-breaking pitcher. For a brief moment in time, the Angels' future under Dipoto appeared bleak.

October 5, 2012 – Angels extend Iannetta for three years and $15 million. Dipoto clearly wasn’t interested in putting Iannetta on the market and bidding for his services.

October 31, 2012 – Angels exercise $11 million option on Santana and trade him immediately to the Kansas City Royals for LHP Brandon Sisk. Another example of Dipoto’s unique approach to the offseason. Rather than simply choosing to decline or exercise a player’s option, he reads the market, decides the player has value to another team and trades the expensive pitcher in return for a much needed depth arm for the bullpen.

November 30, 2012 – Angels trade RHP Jordan Walden to the Atlanta Braves for RHP Tommy Hanson. Hanson’s fastball velocity has plummeted the past two seasons due to various injuries, mostly related to his shoulder. But the Angels have the best doctor in the business on their side in Dr. Lewis Yocum. Yocum informs Dipoto that Hanson’s shoulder checks out and the Angels gamble on Hanson’s ability to return to form (he once was a top of the rotation type of starter). With three years left of control on Hanson, it appears the Angels landed a high risk-high reward starter in return for a former closer with triple digit heat.

December 13, 2012 – Angels sign 31 year old OF Josh Hamilton for five years and $125 million. This deal was more of a “right place, right time” circumstance for Los Angeles. Texas seemed averse to extending an expensive contract to the slugger and face of the organization. The usual suspects of the Yankees and Red Sox were involved in their own little world of avoiding the luxury tax in future seasons, and the new super power Los Angeles Dodgers had no openings in their outfield, leading to Hamilton sort of falling into the Angels' laps. And once again, Dipoto opts to heavily backload Hamilton’s contract. But curiously, the Angels already had too many outfielders. Adding another to the mix just meant they’d be forced to trade. But given their need for starting pitching and Dipoto’s reluctance to pay market value for mediocre starters, this appears to be a strong, yet creative play for the Angels and Dipoto.

December 19, 2012 – Angels trade DH Kendrys Morales to the Seattle Mariners for LHP Jason Vargas. Morales is a solid middle of the order hitter, but the fact remains, the Angels pitching staff is anything but proven, and adding another 200 inning starter to the mix, especially a left handed one, isn’t a bad way to go. This also opens up an outfield defense of Mike Trout in LF, Peter Bourjos in CF, and Hamilton in RF, which most fans will admit is probably the best defensive alignment major league baseball has seen in a while.

In essence, here’s the transformation that’s taken place…

Jeff Mathis to Chris Iannetta

Mark Trumbo to Albert Pujols

Vernon Wells to Mike Trout

Torii Hunter to Josh Hamilton

Bobby Abreu to Mark Trumbo

Dan Haren to C.J. Wilson

Ervin Santana to Tommy Hanson

Jordan Walden to Ernesto Frieri

Tyler Chatwood to Joe Blanton/Jason Vargas

$143 million payroll to $155 million payroll

Considering payroll has only gone up approximately $12 million, this team has improved by leaps and bounds in slightly over one year.

It truly is a fascinating study of how Dipoto went about destroying and recreating a successful Major League organization in only one year. He sold high on prospects, targeted under-appreciated veterans, back-loaded contracts of expensive free agents, read the free agent market and waited until a $3 billion TV deal kicks in. It may seem risky, but consider this. Every Angel position player is under contract for at least three more seasons, the pitching staff allows for prospects Garrett Richards or Nick Maronde to step into the rotation in a year and the bullpen has a steady flow of projectable arms arriving all within the next couple of seasons thanks to a creative draft strategy that involved the Angels investing in low-cost collegiate relievers in the middle rounds while most other teams focused on raw but projectable high school position players. As far as payroll goes, they’ve kept it in check by maintaining a core of inexpensive players (Bourjos, Trout, Trumbo, Iannetta, Callaspo, Hanson, Frieri, Burnett, Madson) until the TV money kicks in and they have a chance to retool the team with prospects or free agents.

A few seasons from now, Dipoto may be heralded as a genius or a fool, depending on how his plans work out. But you have to admire his fortitude. He's attempting to destroy and recreate an entire organization from the ground up (Latin American scouting all the way up through the big league squad) without sacrificing any years as a "rebuilding phase" at the major league level. I'm not entirely sure if that's ever been accomplished, at least not at this magnitude.