Deemed surplus to requirements in Toronto due to his salary, Eckersley became a New York Red Bull this season only to find himself derailed by an ankle injury and, to a lesser degree, difficulties adjusting to his new surroundings.
Now healthy and happy, Eckersley is contributing on the field once again. The 25-year-old from England regained his right fullback position late in the season and started both playoffs games against D.C. United.
Eckersley is likely to retain that role for Sunday's opening leg of the Eastern Conference final against the visiting New England Revolution.
"Richard came in to your team and there was a bit of an adjustment period," said Red Bulls head coach Mike Petke. "Usually you see that with a player coming over from another league or from a foreign country, it takes a while ... To his credit, he never complained. We had many conversations, him and I. He never complained, he didn't give up, throw the towel in like perhaps many people in sports would do after a while. He kept at it and he's doing well now.
"He made the most of his second chance and he's done well with it. He's done well for us and I'm happy for him. It's one of those things as a young coach that you sit back and you're happy about — to see a player like that put in the hard work and reap the rewards at the end."
Eckersley started the first four games of the season before rupturing his ankle ligaments March 30 against Chivas USA. When he returned to training some two months later, he found Chris Duvall had earned the coaches' confidence. Plus the ankle was still bothering him.
He finally got back on the pitch Sept. 28, some six months and 30 games after the injury.
"Sometimes that happens in football," Eckersley said. "You get forgotten about or whatever. You come to a new team and they don't know what your tendencies are, they don't know how you play on a regular basis because you've not that played that may games for them.
"So I just had to keep my head down, keep working hard every single day. To be fair, my girlfriend kept me grounded. ... She was instrumental in keeping me on track."
Eckersley proposed to Nicola in April, struggling to kneel while wearing a walking boot.
New York may just be a 90-minute flight away from Toronto, but Eckersley soon found himself out of his comfort zone.
Eckersley never had a car in Toronto, taking public transit everywhere. But the Red Bulls practice facility is some 40 minutes from the stadium in Harrison, N.J., so he found getting around difficult at the beginning — especially while living in a hotel.
"It was a bit unsettling at the start," he said.
Eventually he got his own place in Hoboken and a car to ease getting around, and he figured out his surroundings.
These days, Eckersley is comfortable in his new home. Manhattan is an easy train ride away.
He speaks highly about the Red Bulls organization. While Toronto is known for looking after its players, New York is "just the same if not better," he said.
He likes the big pitch at Red Bull Arena and says the club really takes care of the players' families at games with their own boxes and food.
He has savoured the playoff atmosphere, saying the away game at D.C. United was like a European contest with the Red Bulls fans singing their hearts out. The only thing close was when Toronto played at Montreal and TFC fans made the trip east.
Eckersley played 72 league games for Toronto from 2011 to 2013, becoming a fan favourite for his lung-busting runs up the flank and tenacious tackling. But he found himself left out in the cold late in the 2013 season as then-manager Ryan Nelsen opted to go with the cheaper Mark Bloom for the last six games.
Nelsen spoke highly of Eckersley as a player and person but said his salary, listed at US$310,000, was simply too rich. Bloom's salary was US$46,500.
Toronto shipped Eckersley to the Red Bulls in late January for a fourth-round pick in the 2017 SuperDraft.
Toronto declined comment at the time when asked if the club was absorbing any of his 2104 salary, which is even higher (US$373,333), thanks to a contract renegotiation to help ease Toronto's 2013 salary cap burden.
Eckersley joined Toronto on loan from English side Burnley FC in April 2011. The loan became a permanent deal in January 2012.
A class act, he holds no grudges about how his time in Toronto ended. He understands the business side of the sport and still speaks highly of Nelsen.
He also remains in touch with several former Toronto teammates and is keen to talk TFC.
As for his play in New York, he believes there is still room to improve as his bond with the central defenders and winger Lloyd Sam grows.
Then there is French icon Thierry Henry.
"He's a great guy," said Eckersley. "He wants to help. If you ask him a question ... he'll try and help you. He's not a big-time Charlie at all. He wants to help people. And he wants to win, he's a winner."
Eckersley's MLS contract runs out at the end of the season so he is unsure of his future.
In July, he was ready to leave. Now things have changed. But in the meantime, there is more football to play.
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