The first time was 2014, when Carr was the second-round pick (No. 36 overall) of the Oakland Raiders and Allen, now the New Orleans Saints coach but then the Raiders' coach, made Carr the first opening-day rookie quarterback in Raiders franchise history.
"He's a very mature individual," Allen said. "He's highly intelligent. He's very competitive. And he can spin it. When you put all those things together along with a tireless work ethic, I just felt like the upside of the player was what we needed to do at that time."
Those characteristics haven't changed, which made the unrestricted free agent the top option for the Saints to solidify a position that has seen five players start 34 games since Drew Brees retired following the 2020 season. Carr officially signed with the Saints on Saturday.
"How I feel about this man, hopefully, me sitting here tells you what I think about him," Carr said Saturday, sitting alongside Allen at his opening news conference. "You gave me my first opportunity.
"Every time we played y'all since we weren't on the same team, I would always tell you, 'Thank you.' In the press conference leading up to that game, I'd say I was always thankful for D.A. because he gave me my chance. He trusted me with the keys to an organization, and to be that quarterback there for nine years, thank you for that. We're just getting started, though."
Carr had nine record-breaking seasons with the Raiders before being released this offseason.
He started all 142 regular-season games he played, and set franchise records for completions (3,201), attempts (4,958), completion percentage (64.6), passing yards (35,222) and touchdowns (217), with 99 interceptions. Last year, in 15 games he completed 305 of 502 passes for 3,522 yards and 24 touchdowns, with 14 interceptions.
He was selected to play in the Pro Bowl following the 2015-17 and 2022 seasons, and never has thrown more than 14 interceptions in a season.
"We were the first ones to reach out," Allen said, noting that New Orleans received permission from the Raiders to pursue a trade for Carr, and Carr visited the Saints, prior to his release. "We were the first ones to show interest.
The newest Saints free-agent roster addition
"Derek was a guy that obviously I knew, but when our personnel people watched the tape and then our coaches watched the tape, he was clearly our No. 1 target in terms of what we wanted to do at the quarterback position. We wanted to be first out there and make sure that he knew he was the No. 1 option.
"I really felt like, and I think we all felt like, when we had a chance to sit down and visit with Derek and he told us what was really important to him, and what was really important to him was going and winning and trying to win a championship, I felt all along that this is going to be the spot that was going to be the best fit."
At least one former and one current Saint helped smooth the path. Brees connected with Carr while Carr was vacationing.
"I sent Drew a text, it was early in the process," Carr said. "He called me and I just asked questions. I asked questions about the organization, I asked questions about (Executive Vice President/General Manager) Mickey (Loomis), (offensive coordinator) Pete (Carmichael), the city, everything. He answered a lot of questions for me.
"A lot of what he said is probably why I'm sitting here today. When someone you respect so much, that you've competed against – I'm not coming here to be Drew Brees, that man is a Hall of Fame quarterback – I'm coming here to be Derek Carr. (But) I have so much respect for him as a player, I have so much respect for him more as a person and a Dad. I watched him at the Pro Bowl, sitting there with his kids and the way that his kids admire him and talk about him. You can tell he's a genuine person, so a lot of what he had to say was going to carry weight with me. A lot of what he said is probably why I'm sitting here today."
And Carr also hooked up with receiver Michael Thomas.
"First time I talked to him on the phone, I don't think he wanted me to get off the phone," Carr said, smiling. "I really enjoyed talking to him. I told Mickey, 'You talk to Mike Thomas and feel like you two could go out there and face the world.'
"I told my wife when I got off the phone, she was like, 'Why are you smiling?' I was like, 'I love this guy.' He's so competitive and I think just the energy he brings, it would be a very exciting time to throw him the football. He wasn't even trying to recruit me, he was just like, 'When are we getting to work? We're wasting time.' I was like, 'I feel the same way.' I think that our relationship has grown through this process and I look forward to hopefully making that relationship grow even stronger."
Carr said the Saints made a significant impression because the team was willing to trade for him even with the likelihood he would be released.
"That meant something," he said. "Not just something, it meant a lot."
But, too, it was meaningful that he believes the Saints' offense will play to his strengths.
"Just the background of the offense, where it's come from, the terminology," Carr said. "It gets back to what I thought were my most productive and successful years. Similar concepts, different ways of getting to certain things and all that kind of stuff.
"As soon as they started talking football and particularly how Drew wanted to play and how seasons went when Drew was here and how that style and that kind of stuff, that was intriguing to me that they can do so many different things no matter who was quarterback.
"They fit. Like when Taysom (Hill) plays, they fit what Taysom can do. When Andy (Dalton) plays, they fit what Andy can do. When Jameis (Winston) plays – all those guys are super talented, but they all do things differently. So I think the intriguing thing to me was whoever was playing quarterback, Pete and his staff was always putting them in the best situation possible for them as a player."
The best situation for Carr, and his family, was New Orleans.
"We chose New Orleans," he said. "We chose this city. We chose the people here."