But there were some lengths he wasn't willing to go to for his then-defensive coordinator last December.
Jordan stood at a podium in Tampa, Florida, and scoffed when asked how Allen would make his case to be a head coach.
"Is he allowed to leave?" Jordan asked. "I'm going to do the opposite. What can I say bad about him? I'm not helping him leave!"
Jordan's plan of sabotage never materialized.
Less than two months later, Allen would indeed become an NFL head coach for the second time when the Saints hired him to replace Sean Payton after the longtime coach resigned at the conclusion of the 2021 season.
As Jordan might have sensed, the tide began turning that night -- when the Saints embarrassed quarterback Tom Brady and the Tampa Bay Buccaneers in front of a prime-time audience -- on the perception of Allen.
Allen's defensive unit dominated as an 11-point underdog, sacking Brady four times, picking him off once and even goading him into tossing and breaking a tablet on the sideline.
The 9-0 win also happened without Payton, who had tested positive for COVID-19 earlier in the week. Payton had selected Allen to assume head-coaching duties.
Not only did Allen get the game ball after the win, but he also largely got the credit. It was his first opportunity to be a head coach after he was fired four games into the 2014 season by the then-Oakland Raiders.
"That was a huge win," said John Fox, who hired Allen for his one-year stint as Denver Broncos defensive coordinator in 2011 before Allen went to Oakland in 2012. "Everybody on the planet knew it was a huge win. To come up big on defense like they did at the end of that, it was one of those moments you don’t forget."
Allen's 8-28 record in Oakland largely appeared to scare off teams. He barely got more than a passing interest for years and was never a top candidate in any coaching cycle. Allen interviewed with the Philadelphia Eagles and Miami Dolphins over the past two years, but he wasn't offered either head-coaching job.
After this performance, however, things began to change.
"When you have as much success as a D-coordinator as he's had in, let's call it the last five or six years ... the resume starts to look real shiny and real good," Jordan said. "Someone in there was going to throw one of those offers you can't pass up on [him]. Luckily, it was us."
Payton previously had promoted Allen to secondary coach in 2008 after hiring him in 2006 as an assistant defensive line coach, but Allen left for Denver in 2011.
The Saints weren't going to let him get out of the building again, so they created a senior defensive assistant job to help defensive coordinator Rob Ryan with his struggling unit.
But those inside, and outside, the building knew he was positioned to become Ryan's replacement if the defense didn't turn things around. The defense was top five in scoring and yards allowed in Ryan's first season but fell to the bottom quarter of the league in both categories in 2014. Another struggling season paved the way for Allen to take over.
Ryan was fired and Allen was promoted 300 days later after a 47-14 loss to Washington. Allen took over the unit and built it back up. The Saints were last in scoring defense in 2015 but improved to No. 10 in 2017 and were a top-five unit in 2020-21. They improved from 31st in yards allowed in 2015 to fourth in 2020 and No. 7 overall in 2021.
Allen was named the Saints' head coach on Feb. 8, two weeks after Payton retired, following the conclusion of a coaching search that included internal candidates such as assistants Pete Carmichael and Darren Rizzi.
It felt almost certain from the start that they would go with Allen. He had considered what he might do if he was ever given a second chance, and the Saints had the things he coveted: a stable environment with a longtime general manager in Mickey Loomis, a solid roster and an owner he trusted.
He probably remembered the advice Fox gave him before he took the Raiders job: Getting the right job is more important than simply obtaining the title.
"When you've done it once before, regardless of how people view your success or not, I was in a position where I was going to make sure it was going to be the right job for me," Allen said. "There's a lot of variables that go into that. ... It just so happens that it all fit here, and that's why this was the best job for me."
Allen has spoken glowingly of the culture the Saints built since he was hired by Payton. It's probably why he largely kept the staff intact instead of making sweeping changes, even bringing back former assistant Doug Marrone to coach the offensive line.
One notable difference is Allen intends to call defensive plays, a change from his belief in Oakland that the head coach needed to be more of a game manager.
Allen also differs from Payton in his attitude on practice vs. game day. While he's had his share of sideline blowups, most famously going toe-to-toe with former cornerback Brandon Browner in 2015, Allen prefers to channel a lot of his energy into practices.
Payton famously had a "game-day Sean" nickname for his antics on Sundays. Most of Allen's ire can be seen in practice, where he tossed out multiple players for fighting this offseason.
"Probably on the practice field, [I] am a little more aggressive," Allen said. "Sean was a little more laid back teaching on the practice field. But yet Sundays was the day that he really got on guys, and I kind of have always been the opposite.
"I kind of try to put the stress on them during the week and then kind of try not to be a distraction for them on game day."
The other changes are more subtle. Allen admitted he's softer around the edges than he was early in his career. He said he believed he had to be tough as a young coordinator and head coach, keeping distance from his players and seeing things only in "black and white."
"It's probably something I didn't do as good of a job of early on," Allen said, "and I've tried to work on that.
"As I've gotten older and more experienced, I understand that there are shades of gray."
Allen also said he drew a "hard line" when he was first named a coordinator, trying as a young coach to figure out how to gain respect.
"A lot of young coaches go through that," Allen said. "And it's really not until you've got a bunch of skins on the wall that you kind of realize, I can just kind of sit back and be myself, and it's much easier when you're able to do that."
Some of that edge will always be there, said Saints assistant Zach Strief, who played right tackle in New Orleans from 2006 to 2017. Strief said he has seen assistants quickly make it clear they weren't ready for a promotion, but he has never felt that with Allen.
"I think he always felt like there was more there, more meat on the bone, so to say, in terms of what he was gonna be capable of. I think that is in people early," Strief said. "And that's probably why I don't feel like there's been a huge change, because I think that is innate."
There were major hurdles in Oakland for Allen to overcome in his first year of 2012: salary-cap issues and lack of draft picks (and assets). There was also a lack of experience at the coaching, general manager and ownership level after the death of franchise icon Al Davis the year before.
But Allen hasn't had to worry about those things in New Orleans considering his long-standing relationship with Loomis and owner Gayle Benson. It has given him time to focus on the day-to-day issues of coaching, and several of those have already come up since he accepted the job.
He had to smooth over feelings with quarterback Jameis Winston after the team's pursuit of Deshaun Watson. He described that relationship as "a work in progress," like all of his relationships with the offensive players.
"I think he's got a lot to prove. And I think he's excited about doing that," Allen said of Winston. "[In a way we're] very similar. Tampa Bay got rid of him and Oakland got rid of me, so why not join us together and see if we can't make something happen?"
He also flew out to meet wide receiver Michael Thomas, who was rehabbing an ankle in California after missing the 2021 season. Allen and Thomas had to get to know each other after Thomas was away from the team for large portions of the past two years after injuring the ankle in the 2020 season opener.
Thomas, whose previous two seasons involved a public feud with the team over his ankle injury and a one-game benching by the team for a fight with former teammate C.J. Gardner-Johnson in 2020, looked happy, healthy and potentially ready to return in the days leading up to Sunday's opener against the Atlanta Falcons.
"Being a head coach is a difficult job," Allen said. "Every day you come into the office, there's gonna be two or three things that you don't expect. And you have to figure out how you're gonna deal with it. So one of the things that I've learned is, expect it.
"Something's gonna come up. Used to, when things like that would come up, you'd get all, you know, pissed off about it. And you now realize, 'Hey, look, these things are gonna happen. Let's deal with it.' And it's all about how you look at it."