Since then, Trout has turned himself into a man Skaggs can confidently say is "definitely the best player in the game today by far."
"I saw it when we lived together," Skaggs said. "I saw it all the way back then that he was going to be a superstar."
Skaggs, reacquired by the Angels on Tuesday in the three-team trade that also brought in former White Sox pitcher Hector Santiago, still has his room in Santa Monica, Calif. Heck, Skaggs still has the same old worn-out Halos poster hanging from his wall -- of Darin Erstad, Tim Salmon, Troy Glaus and Ramon Ortiz rocking the periwinkle uniforms under the words: "It's All About Baseball With the Angels."
Skaggs was a true Angels fan -- just like the guy he was traded for, Mark Trumbo -- and he's hopeful that a return to the organization he always wanted to play for can help take his career to the next level.
"It's just funny growing up, watching all these guys, wanting to be on the Angels and then getting drafted by them, and now coming back to them, and hopefully getting to the big leagues with them," Skaggs said in a phone conversation. "Everything's kind of coming full circle. It's a blessing."
At 17, Skaggs was plucked out of Santa Monica High School in a 2009 First-Year Player Draft that might one of be the best in Angels history. With its first four picks, the club selected Randal Grichuk (24th), Trout (25th), Skaggs (40th) and Garrett Richards (42nd).
"And don't forget about Patrick Corbin," Skaggs said of his ex-D-backs teammate, who was taken in the second round.
Like Santiago, Skaggs -- 22 years old with an athletic, 6-foot-5 frame -- is young, throws left-handed and has an option year left. Unlike Santiago, who is almost assured a spot on the 25-man roster either as a starter or a reliever, Skaggs will to have to earn a rotation spot out of Spring Training, with the Halos expected to add a free-agent starting pitcher.
Skaggs' surge through the D-backs' Minor League system took a drastic hit in 2013, when he lost a Spring Training battle for the fifth spot in Arizona's rotation, struggled in Triple-A (4.59 ERA, 3.4 walks per nine innings, 1.47 WHIP) and got hit around during another short stint in the Major Leagues (5.12 ERA in 38 2/3 innings, after a 5.83 ERA in 29 1/3 innings the year before).
Most concerning of all, though, was a drop in fastball velocity.
"[Skaggs] went to [Triple-A] Reno and the velocity was of some concern to us; it went down from mid-90s to 88 or 89 at the end of the year," D-backs GM Kevin Towers said at the Winter Meetings. "He did not have the confidence in his fastball command that he had in the past. It may be a mechanical adjustment, who knows?"
And if there's anyone who could figure it out, it's probably the current Angels GM.
Dipoto isn't just the man who has traded for Skaggs twice in 40 months; he was part of the D-backs' front office that wanted to take Skaggs with the 41st pick in 2009, right after the Halos ultimately took him off the board.
Dipoto called Skaggs' Minor League progression "perfectly normal," noted he's been young for every level he's played at and said the Angels "saw roughly the same pitcher" in 2013, except "with a greatly improved changeup."
Dipoto admitted there was a "slight drop-off in velocity, but only at the big league level late in the season when ordinarily guys are tired." Skaggs, Dipoto added, "is not built on power." He's at his best when he's sitting somewhere between 88 to 92 with his fastball, using it to play off his plus curveball and changeup.
But Dipoto did notice a mechanical flaw, one he believes is very fixable: In an effort to kill velocity and create more dive with his changeup, Skaggs has developed "a little bit shorter stride length," which may have diminished some of his other stuff.
"We think that a 22-year-old with a clean bill of health and a good performance history as a Minor Leaguer and the kind of physical stuff that he has really bodes well for us," Dipoto said.
Skaggs believes his struggles last year were "more mechanical," but didn't want to get into specifics. Asked what he took away from last year, Skaggs said, "Everything."
"You just grow with every start as a pitcher -- especially me, having just a handful of starts in the big leagues," he added.
"I'm definitely working hard on getting my velocity back, lifting weights and really just kind of getting back to my old self. And I think coming back to the place where it all started will really help me out."