ANAHEIM, Calif. -- It all began with a simple question, posed around the middle of last summer. The Los Angeles Angels' three most important decision-makers -- owner Arte Moreno, president John Carpino and general manager Billy Eppler -- wanted to know if Mike Trout would listen to offers ahead of free agency. They asked his agent, Craig Landis, who relayed the message to Trout, who rationalized the dilemma with on-brand simplicity: Yes, he would listen, and yes, if the numbers made sense, he would consider it.
That seed finally sprouted Sunday afternoon on a makeshift stage in front of the main gate at Angel Stadium, as approximately 3,500 fans arrived early for an exhibition game to celebrate the 12-year, $426.5 million extension that made Trout the richest athlete in North America.
Trout said it "never crossed my mind" that he wouldn't return to the Angels, not even when it seemed that the rest of the world was picturing him in the Northeast. The Angels signed Trout through the 2030 season, by which point he will be 39 years old. They secured the greatest player of his generation for his entire career two years before he was scheduled to reach free agency, despite never winning a playoff game with him.
There were questions about whether Trout would inevitably sign with the Philadelphia Phillies, who reside close to his childhood home in New Jersey. There were questions about whether the Angels should entertain the idea of trading Trout if they couldn't secure a commitment. There were questions about whether the Angels had already lost Trout by failing to win with him.
Moreno, 72, tried to shove those aside.
"I'm a very optimistic person," he said. "You put me on the bottom of a mountain, I'll look over at my buddy and say, 'OK, we're going up.' He'll look at me like, 'You're nuts.' We may not get there in one day, we may not get there in a week, but we're going to climb it."
That climb reached a critical juncture on a random spring afternoon earlier this month, when Trout came out of a game and, as is his custom, walked toward the netting behind home plate to shake Moreno's hand.
"Can I have 10 or 15 minutes?" Moreno asked.
In the thick of the negotiation, with uncertainty still looming, Moreno sought a face-to-face meeting with his superstar center fielder. They sat inside the manager's office at Tempe Diablo Stadium and went over everything, from the team to the future to the fans to Trout's overall experience as a member of the Angels.
"We ended up in there an hour," Moreno said, "talking about all kinds of stuff."
Eppler called the Moreno sit-down "really big" with regard to completing the agreement. Two days later, Trout sent Eppler an early-morning text message asking if the two could meet privately, which prompted Eppler to book a hotel room in Arizona.
"At that point," Eppler said, "I started to feel like we had an opportunity to get something done."
A deal was completed only a week or so later, but there was no seminal moment that made Trout an Angel for life.
It was how they treated him over time -- how they chipped in a little extra money after his second year, how they supported him in the wake of his brother-in-law's sudden death, how they stood behind him when Major League Baseball questioned his desire to be marketed. It was the way Eppler improved the farm system and communicated his vision. It was the appeal of living in Laguna Beach and those 2,800 miles that separate his baseball life from his home life.
It was Trout, who ultimately didn't want to mess with what he considers a good situation.
"I never gave it higher than a 50 percent chance that he would be a free agent because I knew Mike liked it here," Landis said. "If the Angels really wanted to sign him, and they made him a generous offer, it was going to be very difficult for him to turn it down because I know Mike's never been about making the last dollar."
As summer turned to fall, the Angels' front office kept floating the idea of a looming offer. But Trout and Landis thought it best to wait a few months. They wanted to see who would become the new manager, who would join the roster in the offseason and, most importantly, what type of contracts Bryce Harper and Manny Machado would get.
Eppler checked in again in January, asking if Trout was still willing to listen before free agency, and the answer remained the same.
For Trout's first extension -- negotiated with Jerry Dipoto as GM -- an assortment of options were floated, ranging from short-term to long-term to even a lifetime deal. For this one, the demand was clear: Trout wanted this to be his last contract, which meant tacking on 10 years to the two seasons that remained on the six-year, $144.5 million extension he signed in spring 2014. The Angels didn't want any opt-outs, and Trout's side came around to that quickly.
When offers were exchanged beginning in late February, the Angels expressed trepidation about paying too much money deep into an athlete's 30s, fearful of reliving the Albert Pujols situation. The three or four weeks that followed revolved mostly around how the average annual value would reflect that.
"We had a gap, and it got whittled down," Landis said, unwilling to go into specifics. "They came up, we came down, and we got to a level that both sides ultimately felt comfortable with."
From the dais, Moreno laughed about how "everybody was holding on for the last 30 to 40 days." Trout joked about how he spoke more to Landis during that time than his own wife, Jessica.
In those conversations, Trout kept going back to one point: He knows he likes it with the Angels, but he doesn't know if he will like it elsewhere. Landis also reminded Trout how difficult it is to predict which teams will have the money to sign players when the price points get so high, a reality perhaps best exemplified by Machado's joining the San Diego Padres.
In the end, Trout didn't believe that the extra money he could secure in free agency was worth the uncertainty that clouded it.
"Spending your whole career with one team, I think, is pretty cool," Trout said. "That was one thing on my mind, talking to people -- if I did leave in two years, maybe looking back, I would've probably regretted it a little bit because I love it here."
The Angels are now tasked with the responsibility of building around Trout. They were aggressive early, spending nearly $450 million on Pujols, Josh Hamilton and C.J. Wilson from 2012 to 2013. The deals set them back, prompting them to navigate that awkward middle space between building for the future and trying to win in the present.
Now, as Moreno pointed out, the budget is opening up. Besides Trout, just Pujols (through 2021) and Justin Upton (through 2022) are signed beyond the 2020 season. Then an Angels farm system headlined by Jo Adell and Griffin Canning should provide low-cost production.
Moreno said the Angels will have "all kinds of flexibility."
"We're going to continue to build something sustainable here, something healthy here, and expect to perennially be one of the top teams in baseball year in and year out," Eppler said. "That's our standard."
Eppler, formerly a key executive with the New York Yankees, has gained a deep admiration for Trout since becoming the Angels' GM in October 2015. He stood at the lectern Sunday and gave an impassioned speech about how Trout is driven not just to be "special" but also to be "significant" -- a nod to Trout's ability to make others better. He was asked what he has learned about Trout since joining his team and answered the question by saying, "If the house next door to me opened up, I would really hope Mike and Jessica Trout moved in."
Later, Eppler brought up a question the late Yankees executive Gene Michael always asked in these instances: Can you trust the player with the contract?
"There wasn't somebody that I've come across that checked the boxes like Mike does," Eppler said. "You trust his intentions, you trust how he's going to take care of himself, how he's going to approach the game, how he's going to be inside the clubhouse. You trust all of those things. For us, it was a pretty easy visualization."