Timing is everything for Leon Bailey and, with Bayer Leverkusen back in the UEFA Champions League, the 2019/20 campaign could be a prime time for the Jamaican to take the next step in a career packed with potential.
Whether it be his dazzling footwork, blistering pace or career choices, Bailey’s game revolves around decision making both on and off the pitch.
Discussing his move to Germany, he told bundesliga.com earlier this year: “I chose Leverkusen because I thought I needed to take the next step in my career.
"Leverkusen is an awesome team. They’re always in the Champions League, always doing well in the Bundesliga. Basically, they always want to help their players go a step higher. I think this was the perfect choice for me after Genk."
Watch: Leon Bailey's Bundesliga Mixtape!
The 21-year-old got his first taste Champions League action shortly after joining Die Werkself in January 2017, featuring for a grand total of 15 minutes in a 4-2 aggregate loss to Atletico Madrid in the last 16.
Since then, Bailey has had to be patient in waiting for another chance to test himself against the continent’s elite and it hasn’t always been smooth sailing.
After some initial teething issues, the Jamaican captured the imagination of Bayer’s fans in his first full Bundesliga season, notching nine goals and laying on a further seven assists. However, an inferior goal difference would ultimately prove Leverkusen’s downfall in their bid for a top-four finish.
Just when it looked like his career was about to take off though, Bailey stalled somewhat in 2018/19. The Jamaican made 16 Bundesliga appearances under Heiko Herrlich in the first half of the 2018/19 campaign, but only eight of those came as a member of the starting line-up. By the winter break, he had just a one goal and one assist to his name.
Watch: Relive Leon Bailey's stunning 2017/18 campaign!
Herrlich managed to rekindle the club’s burning ambitions in the lead up to Christmas, but after failing to save his job it was Peter Bosz who doused them in gasoline when he took over as head coach.
Bosz’s brand of eye-catching attacking football saw the goals flow freely, with only Bayern bettering Leverkusen's tally of 43 goals in a memorable Rückrunde that saw them snatch fourth place on the final day to punch their European ticket.
Kai Havertz, Julian Brandt and Bailey were all major beneficiaries of ‘Bosz-ball’, as it is fondly known, and plenty of column inches were dedicated to the trio's role in the Dutchman's revolution - something the youngster foresaw when Bosz first took over.
"I’d say Peter Bosz being here is a big thing for me because he has a different style of play, and I didn't feature much in the first part of the season," he told bundesliga.com back in January. "It’s perfect for me because he likes my style of play and I like how he wants us to play. I think it’s going to help the team a lot and it’s also going to help the way I play."
In the first half of the season Bailey was involved in 50 shots on goal, a figure that rose to 77 under the Dutchman as the element of risk returned to the youngster’s game.
While he didn’t quite hit the heights of his jaw-dropping performances from the 2017/18 season, it was clear for all to see that Bailey’s new lease of life on Leverkusen’s left flank had restored his confidence. Reference his free-kick against Bayern Munich from Matchday 20 if you need proof.
The stunning set-piece was one of four goals he added to a tally that may have risen had a hamstring injury not ruled him out for the high-scoring affairs against Augsburg, Eintracht Frankfurt and Hertha Berlin at the business end of the season.
Bailey did recover in time to feature at the CONCACAF 2019 Gold Cup as part of the Jamaica side that got knocked out by the USA in the semi-finals though. In four outings he didn’t get on the score sheet, but having got his first taste of a major international tournament, now another prestigious competition will capture his focus
The 15 minutes of Champions League action from 2017 wasn’t enough to quench the Jamaican’s thirst for an opportunity to demonstrate his capabilities on the continental stage. As he looks to take the “next step” in the 2019/20 campaign, Leverkusen have reason to believe that the Bosz-Bailey connection can grow even stronger and, with Brandt now on Dortmund's books, the Jamaican has a chance to unlock even more of his potential.
Bailey believes the Champions League is where Leverkusen are “meant to be” and under Bosz’s tutelage, next season is the perfect time to finally prove the same goes for him.