On January, 6, 2019, in his first NFL playoff game, the Baltimore Ravens rookie quarterback had been restricted to under 200 yards passing by the Los Angeles Chargers, he was sacked seven times and the offense he led failed to score a touchdown until midway through the fourth quarter, at which point the game was gone.
Boos from his own fans ringing in his ears; critics questioning whether he could make it as an NFL quarterback.
He told his personal quarterback coach Josh Harris he needed some time off before they reconvened for their offseason work.
When they did, two weeks after the New England Patriots won Super Bowl LIII, the aim was to get back to basics.
"This is going to be a very slow offseason and it's going to be boring," Harris told Jackson.
Sometimes they would spend an hour mimicking the basic action of the throwing motion. Some days that was all they did.
Other days Harris would swing a broom at Jackson's legs, abdomen and head to replicate the pressure he feels in the pocket.
"He hates the broom drill," Harris told Omnisport.
"I always do this after he frustrates me to scare him. 'If you don't listen to me, I will hit you with this broom!'"
The mantra all offseason was "finding your rhythm" and Harris preached it for four days a week. It was supposed to be five but Jackson "always found a way to get out of Fridays".
On September 8, 2019, in his first NFL game of the season, Jackson got the chance to put the lessons he had learned with Harris just 26 miles away into practice.
He threw for 324 yards, torched the Miami Dolphins in their own stadium with five touchdown passes and had a perfect passer rating. It was the start of a campaign that would end with the MVP award, given to him in the same city on Saturday night.
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Harris has known Jackson since his college days at Louisville. Jackson's mother, Felicia Jones, and his youth football coach, Van Warren, believed Harris could take the quarterback's game on. They were right, he won the Heisman Trophy later that year.
"He never acted like a person that was this gifted at football," Harris said.
"He's very teachable. He's a perfectionist, he gets frustrated when things aren't going well."
And if Harris wants the perfect rep out of Jackson, he knows just which buttons to push.
On his iPhone Notes app are a series of criticisms pundits have levelled at Jackson. Comments from the people who didn't think he could throw. Those who, like former Buffalo Bills, Carolina Panthers and Indianapolis Colts general manager, Bill Polian, thought he should change position.
"You can see when you give him a criticism, it turns into fuel," Harris explained.
"I've had other players, they wither under it. It motivates him, he's seen that [criticism] every step of the way."
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The critics did not think Jackson, unquestionably an elite talent with his legs, would ever be able to lead the NFL in touchdown passes - as he did in 2019 with 36 scores.
So when Harris was designing Jackson's unique pro day before the 2018 NFL Draft, the aim was to prove to those in attendance that he could win from the pocket. Jackson took every snap from under centre and threw to multiple receivers instead of just one.
Pittsburgh Steelers head coach Mike Tomlin was there and so was Baltimore's quarterback coach James Urban, who impressed Harris by showing a keen interest in his drills.
When it came to draft night, Harris wore a purple tie, hoping it would prove a lucky omen and that his pupil would be selected by the Ravens.
One by one the players on the tables next to Jackson that night in Texas were drafted. Saquon Barkley to the New York Giants. Josh Rosen to the Arizona Cardinals. Jaire Alexander, Jackson's college team-mate, to the Green Bay Packers.
Soon only one pick remained in the first round. Amputee linebacker Shaquem Griffin was in the green room, though he was never going to be selected that high, as were running back Derrius Guice, and Jackson, whose entourage had flights booked back for the following morning thinking he would be chosen in the first round.
All-Pro cornerback Jalen Ramsey had stuck around too, an interested observer in Jackson's fate.
When Guice's phone rang with the Philadelphia Eagles on the clock, Harris figured he knew what that meant. But there was another call coming into that room, to Jackson's phone.
"Everybody's in a daze," Harris said.
"He's just sitting there. I slapped him, 'Man, pick up the phone!'"
It was the Baltimore Ravens. They had traded up to select Jackson with the final pick of the first round, a move that would look incredibly shrewd less than two years later when he led them to an NFL-best 14-2 record.
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Harris was a little worried as Jackson continued to compile an MVP-calibre campaign. The sensational 47-yard touchdown run against the Cincinnati Bengals. The ludicrous touchdown pass to Mark Andrews when off-balance in Cleveland. The accumulation of yards on the ground (1,206) that would see him break Michael Vick's single-season record for most among quarterbacks.
"He's the media darling now," Harris thought.
Where then was he going to find the criticism to fuel Jackson?
Then came the shock 28-12 Divisional Round playoff loss to the Tennessee Titans, which happened despite Jackson producing over 500 yards of total offense.
Not only did the Titans' defensive scheme give Harris and Jackson something to mull over this offseason, it also provided the coach with some new entries for his iPhone Notes.
"They're saying you're 0-2 in playoff games," Harris intends to tell Jackson when they next meet.
"They were even critiquing your precision passing in the Pro Bowl skills challenge.
"I know it's silly but cool, I can use it."
Jackson will trot back out onto the practice field in Pompano Beach in two weeks' time as the freshly crowned MVP - the best player in the entire NFL.
But Harris will be ready, with his iPhone Notes, and his broom.
"I already know how to motivate him," Harris concludes.
"I've got a couple of bullets in the chamber for the MVP!"