It was supposed to be their year.

Coming off an 86-win 2011 season, the Angels pulled off one of the most jaw-dropping moves in hot stove history, signing Albert Pujols to a 10-year, $240 million contract. When the Halos locked up the best player on the planet and lefty starter C.J. Wilson within a matter of hours, the baseball world wasn’t merely convinced that the Angels would contend in 2012; we thought it could be the beginning of a dynasty.

The Angels responded to all of that hype by winning … 89 games, a three-game improvement that resulted in a third-place AL West finish and a third consecutive season missing the playoffs.

Things have only gotten worse since. The Angels doubled down on the Pujols and Wilson signings by inking Josh Hamilton to a five-year, $125 million contract, only to see his numbers plummet following his 2012 walk-year joyride in Texas. Amid debilitating injuries for Pujols, generally spotty pitching, and iffy performances from too many Angels not named Mike Trout, the Angels sputtered to a 78-84 finish in 2013.

Not ones to stand pat, the Angels made dramatic roster changes for the third winter in a row. In a three-team trade, they sent Mark Trumbo to the Diamondbacks, netting young left-handed starters Tyler Skaggs and Hector Santiago. Then, cashing in outfield depth to fill a gaping hole, they flipped defensive whiz Peter Bourjos to the Cardinals for veteran third baseman David Freese.

Justin Hollander has witnessed the Angels’ rise and fall from up close. Hired in January 2008 following the second season of the team’s three-year AL West title run, Hollander initially served as a player development and scouting assistant. He’s since gone from a jack-of-all-trades role that included advance scouting, data analysis, draft and arbitration prep work, and contract assistance to his current role as the director of baseball operations. He’s seen the front office evolve from a small inner circle of nine, in which he was the only person looking closely at data (and the youngest guy in the room by a mile), to a larger, blended group that includes a more balanced mix of scouting and numerical analysis.

Amid the Angels’ 2-4 start, Hollander spoke with Grantland about the Pujols and Hamilton deals, last offseason’s trades, Trout’s greatness, and more.

When word came down at the 2011 winter meetings that the Angels had signed Pujols, everyone wondered how you guys had pulled it off. He was the best player alive, and Jerry Dipoto was a new GM. Walk us through how the Pujols and Wilson deals went down.

I remember sitting with Jerry, talking about Pujols, right around Thanksgiving. We get to the winter meetings a couple weeks later, and you’ve got the pro scouts, the AGM, special assistant to the GM, the scouting director … for the first time Jerry had everyone together. It’s the first time we were all able to talk freely about ideas. It’s me, [assistant GM] Matt [Klentak], [assistant GM] Scott Servais, [pro scouting director] Hal Morris, Jerry, and we’re all sitting there, asking if was this was the right thing to do, and if so, can we get this done.

On the second day of the winter meetings, we’re working on a theoretical model for a Pujols contract. Jerry comes in and says, “I think we’re going to sign Albert Pujols. What do you think?!” All I could say was, “Wow.” It’s funny how the winter meetings work. Things can happen so quickly, but it can take forever. Maybe a half an hour goes by without hearing from Jerry, but it felt like three days. He’d been talking to [owner] Arte [Moreno], [Pujols’s agent] Dan Lozano, and Albert. And we’re just sitting there thinking, What’s going on? What’s happening?! Should we send him some food?! Finally Jerry comes back into the suite where we’re all sitting. He’s one of those guys who can be really hard to read. This time, we caught the look on his face. He couldn’t have been easier to read — it was clear he had news to share.

We didn’t actually get the deal done with Albert until the next night. We knew we were at least the front-runners by that point, but it wasn’t official. We finally got it done about 12:30, one o’clock the next morning. C.J. happened that night, too. He was there, at the winter meetings. Matt, Scott Servais, and myself walked into C.J.’s room at about 3:30, four in the morning. He was sitting there, eating scrambled eggs; we all grabbed a few fries. Some time after four, we finally got the letter of agreement done. It’s the morning of the Rule 5 draft, I’m going to bed at 5:15 in the morning. And a few hours later, our team president, John Carpino, is on a plane back to Anaheim, with letters of agreement from Albert and C.J. in hand.

It’s easy to say now, since the first two years of Pujols’s contract haven’t gone as well as hoped, but even at the time there had to be at least some concern about how he might age. How much did that factor into the decision-making process?

That was a personal project of Jerry’s. He’d been keeping copious records on how players age for years. He had lots of data, especially on how generationally great players age, the guys you’d call 80s on the scouting scale. He looked at what their career arcs were. Do they suddenly go from 80 to 40 or 50, or 80 to 60 or 70, then level off at that point, or something else? What he found, and what we found when we expanded on those studies, was that the guys who were the 80s, unless there’s a health catastrophe, it’s very rare that they just suddenly stop being great players. As they age, their prime tends to last a lot longer, and their post-prime tends to be better than most players’ prime. Players who control the strike zone and take their walks especially — Chipper, McGwire, Edgar Martinez, whose career started late but whose hallmark was controlling the strike zone and being a good all-around hitter — those players stayed productive deep into their thirties, or even beyond. Same thing for 80s from further back: Willie Mays, Hank Aaron. Overwhelmingly, what we found going back through history was that guys who are generational hitters don’t age like normal players.

So you signed Pujols and Wilson. The media went crazy. What did you expect heading into 2012?

We thought we were really good, that we had a chance to win the World Series, even without Mike Trout turning into an instant superstar. We traded for Zack Greinke during the season to add to all of that. So it was frustrating when it we came up short. We played so well in some stretches, but poorly in others. Oakland and Texas just played better. It doesn’t matter if we thought we were the most talented team, both going into that year and throughout that year. We did it to ourselves.

Why do you think the team fell short of expectations?

No one particular reason. We had a poor bullpen, but then we acquired Ernesto Frieri, and he’s been awesome from the time we got him up until now. The starting pitchers went through a lapse post-All-Star-break, where we struggled both with normal health and getting deep into games. We got off to a slow start, and that was a tough hole to come out of. There was nothing in the postmortem that we felt was a permanent, unfixable thing.

So what was the thought process heading into 2013?

It’s important to know who you are. You have to know your true talent level, how it plays in the [present] and how it might play in the future. I don’t think it does you any favors to think you’ll perform at a 99th-percentile level, or first percentile. Whether it’s scouting, stats, health, you have to be honest with yourself.

Let’s talk about Hamilton. He was coming off a gigantic overall season when you guys signed him, but he’d been chasing bad pitches; even though he’d always been a free swinger, it looked like he was lost at the plate at times. Did you see Hamilton as a superstar, MVP-caliber player, or were there some doubts about his strike zone judgment?

Well, keep in mind he did have a [.930] OPS that year, and almost .900 in September. He had that monster start, not a very good June [or July], then he comes back and he’s a really good player after that. Josh is unconventional. He won’t control the strike zone like Trout or Pujols does; if he started doing that suddenly in his early thirties, that would make him almost unique in baseball history. He moved from a great run environment to a much more pitcher-friendly one. We didn’t expect him to start racking up 40-homer seasons necessarily. But he has made some adjustments. He’s hit .350 before, and he’s been a damage hitter, crushing balls to parts of the park that just about no one else can reach. The talent exists for him to adjust, and to do it in different ways.

How do you see these guys performing in 2014, starting with Pujols?

The 2012 Pujols that we saw, where he put up those big numbers from May 15 on, that’s the version we think we’re going to be getting. He’s moving around great; his defense is exceptional. I don’t think people realize how much pain he was in. Even with simple things like trying to get up and down the dugout steps, he was literally on one leg. And it’s just so hard to do that, especially when you’re hitting. He takes extreme pride in being out on the field; he wants so badly to help that he thinks he can do it on one leg. If this were a lingering problem, it would be a concern. But all reports are that he’s healthy. We’re very excited to see what we have 1 through 9, to grind out at-bats, and score a lot of runs. We have a really good group when everybody’s healthy.

What about Hamilton? He experienced such a big drop-off last year, and it didn’t seem to be due to injuries.

One of the things that’s been written about this spring is that it’s a bigger, stronger Hamilton, hashtag BestShapeOfHisLife. And it’s true, he is noticeably bigger and stronger this year. Last year, he lost a lot of weight to try and stay on the field more, to impress his new team. He was 240-plus in Texas, down to 215 last year. Josh is a big person, and he probably just was not used to moving his bat through the zone at a lesser weight. Also, baseball players are very routine-oriented, and the new park and the new environment could have thrown him off. In the second half of last year, he was closer to being the normal Josh Hamilton, even at a lesser weight. Then he gained 25 to 28 pounds of healthy muscle this offseason, to get back to his old weight. And he spent a lot of time with [hitting coach] Don Baylor on the back fields, taking live BP, working on getting back to being Josh Hamilton.

We haven’t even talked about Trout yet. Did you have any inkling that he would be this good, and especially this fast?

I was one of the few people sitting in the draft room at the time who’s still with the team. I was sitting next to the East Coast scouting supervisor, and the descriptions and adjectives were so over the top. He’s this 17-year-old kid from New Jersey, and the comp that the supervisor made was Rickey Henderson. But you know what? He was kind of right! The thing that separates [Trout] from just being a talent is everything else. He has such a feel for hitting and for fielding, so much confidence at the plate, his aptitude is off the charts, his makeup is off the charts. Every box you can check is an 80: attitude, athleticism, plate discipline, power, all the physical tools — and add the mental tools to do it. That’s when guys can flip the switch and reach their peak very quickly. We did expect Trout to be an All-Star performer at some point, just not in the first 30 days of his career. Mel Ott, Griffey, Mays — so few guys become this good, this quickly.

Trout has shown a real propensity for taking away home runs and making things happen on the bases, but given the injury risk of those physical plays, is there any thought to reining him in at some point?

At this point in his career, it’s probably up to the player. He’s 22 years old, so it’s not like he needs a break from the wear and tear. Plus, everyone’s always talking about hidden value — Trout is the best baserunner in the league. He steals all those bases, of course. But he also cuts corners incredibly, gets great reads, and knows when to go for the extra base. At 22, I don’t know that anyone wants to have a conversation about toning that down. Look at it like this: Trout gets on first, steals second, Pujols hits a single, Trout scores. That has real value. If he weren’t so good at it, if he were running into outs, fine. But obviously he’s not doing that.

The biggest change this offseason was trading Trumbo, which netted two young starting pitchers in Santiago and Skaggs. What was the thinking behind that deal?

You always have to be mindful of the future, of what your team will look like for the next three years, the next five years. We needed to get more sustainable. We knew that signing veteran starting pitchers to fill the last two spots in the rotation wouldn’t work long-term. You want the last two or three guys in the rotation to be guys coming up the ladder, rather than down the ladder. For us, that’s [Garrett] Richards, Santiago, and Skaggs. Santiago and Skaggs are bat-missers. Richards has that heavy curve and slider, he’s already a big groundball guy, and we think he’ll miss more bats as he gains more experience. When you have guys like Pujols, Hamilton, Wilson, [Jered] Weaver — guys making real money — you need guys you can control. It’s very hard to get two players in the same deal where they have real ability, and you can keep them for multiple years. That’s rare. It wasn’t easy to give up a good homegrown player, especially someone like Trumbo, who’s from Anaheim and is very popular here, but these were two pitchers we really wanted.

One move that drew a lot of criticism in analytical circles was trading Bourjos for Freese. Critics said Bourjos was a more valuable player overall, and Freese was older and more expensive. What was the rationale for that deal?

It was a matter of having the right assets in the right places. Having two center fielders is great, but when your best outfield is Hamilton, [Kole] Calhoun, and Trout, your other asset can’t play. To turn that into someone who can play every day for you makes a lot of sense.

Was Bourjos as attractive on the trade market as a stat like WAR indicated he might be?

Like the arbitration market, defense is often undervalued in trades. There are teams that value defense, but it’s much easier to trade a great hitter than someone who’s a prime contributor defensively. Sometimes FanGraphs value doesn’t translate into what other teams value. With Freese, we feel like we got really good value. Third base has not been an easy position for the Angels to fill. I looked up this nugget: Freese’s career OPS+ is 115. Only once since 2002 has the primary third baseman for the Angels hit that well.

Was Freese’s playoff experience a factor?

That was something we looked at this offseason: What players bring to the culture of the team. What kind of people are they? Are they adders to our environment, or are they neutral or negative? You would never say you want an unproductive player who happens to be good in the clubhouse. But if you have players of similar [ability], this is something you want. We want to create a culture of winning and accountability.

Are there other ways to build that culture?

We brought in Don Baylor, Dave Hansen, and Gary DiSarcina to supplement our club with some of that good culture. We want to provide every resource we can, give the players everything they need to go out and win games. It’s a really talented group, with the coaching staff to get the most out of them.

Baylor has been one of the best hitting coaches for a long time. [Baylor is currently sidelined after breaking his leg while catching the ceremonial first pitch on Opening Day.] He brings a great presence. Dave Hansen is a nice complement to Baylor’s demeanor; as an assistant hitting coach he’ll be in there helping with the little things every day. With DiSar, we’re getting a different perspective, since he’s bringing information over from somewhere else, having been the Red Sox Triple-A manager last year.

Then we’ve got Rick Eckstein. He’s our eye in the sky, our seventh coach, our self-scout. He’ll sit in scout seats, go through pregame work, sit with Nick Francona and Jeremy Zoll in advance scouting meetings, look at defensive positioning with Nick and Jeremy. Are we tipping pitches? Is the infield lining up in right spot? How are our secondary leads? He’s advance scouting our own team. Several other teams have this; the Padres and Rays were early adopters. We feel like the combination of Rick, Nick, and Jeremy — it’s data combined with coaching, and that helps the process go more smoothly. A big goal of ours has been to answer the question, “How do we translate information from the front office to the field?” There’s so much data on the field. You can’t just drop a 200-page packet in a player’s hands, then say, “Go get ’em!” That’s really hard! We’ve tried to help that process along by ripping up our advance scouting approach and starting over with these new ideas.

What’s the team outlook for 2014?

We’re absolutely optimistic that we can and should contend. We probably don’t have the team that we’ll have late in the year; guys grow into roles and change, and we have the flexibility to make additions. If we need to supplement our roster with something, we have the ability to do that. For now, it’s about making the smartest decision, not the impulse decision. The smartest thing we could do was let Skaggs go out and have an opportunity to develop into a really good major league pitcher. To let Calhoun play right field every day for us. To give Santiago a chance. We’re a better organization if we let those guys play and grow into roles than if we don’t find out what we have.

This interview transcript has been lightly edited for clarity.