Club Roots is an ongoing series that examines the people, philosophies, and pathways that have shaped the Portland Timbers player development pipeline.
In part 1, we spoke with Portland Timbers Technical Director, Jack Dodd. He spoke about the principles that define the club's development and aligning those principles across all levels of the organization. In part 2, we spoke with Timbers Academy Head Coaches Darren Back and Fernando Pessoa. They spoke about laying the foundation for the next generation of Timbers players and preparing those players for the next phases of their careers as players.
In part 3, we speak with Timbers2 Head Coach Jack Cassidy. Jack has the unique role of leading Timbers2, which serves as the developmental bridge between the academy and first team.
Cassidy arrived in Portland in January of 2026 and brings nearly 15 years of experience across the academy, professional development, and first team environments in Sweden, the United Kingdom, Denmark, and the United Arab Emirates. Most recently, Cassidy was a first-team assistant coach and head of individual development at Aalborg BK in the Danish Superliga.
In our conversation with Jack, we talked about his coaching career, the differences between senior and academy player development, working with his fellow staff, the American player development system, and what he wants Timbers supporters to get out of Timbers2. Enjoy Stumptown Footy's conversation with Timbers2 Head Coach, Jack Cassidy.
STF: You’ve coached across the academy, senior developmental, and first team environments across Europe and the Middle East. Each of your previous stops offers various opportunities for you to grow as a coach. What thread runs through each of these experiences that you are now bringing to Timbers2?
Jack Cassidy: I think the demands of the game are similar wherever, wherever you go, in terms of what's required to sustain a career in the professional game. And I think that it's such a difficult jump that final hurdle between whether it will be B team, second team under 21's, depending on what country and context you're in. But some of those things are really important in terms of any country you're in. Those characteristics going from second team to first team don't really change, to be honest.
STF: Before coming to Portland, your most recent role was first team assistant coach and head of individual development with Aalborg. How does the first team lens shape the way you approach a developmental role like this one?
Jack Cassidy: I think you can help support the players in terms of what the demands are like. I know what the demands are because I've been on the other side of the fence, where your job is to win football matches. Now we want to win like football matches as well, of course. But of course, you've got less pressure.
I was involved in a relegation battle last year, so tensions are high. People's jobs are on the line. I know relegation doesn't exist here, but when you get relegated in Europe, people from the office lose their jobs, not just the football side. So there's a lot at stake. So young players need to understand the pressures that come with stepping up into a first team and the demands and the things that they need to do to win the trust of a first team head coach.
STF: T2 serves players who are at various stages in their Football careers. Some of these players are getting their first tastes of professional football, while others have been in their careers for a few years. How do you balance coaching players with such varied needs of professional development?
Jack Cassidy: We take an individualized approach with the group, really. So the first thing we speak about is that connection. So, trying to build really strong relationships with the staff and the players to really understand them and their needs. Our aim really is that when they leave us, no matter what the duration of a contract is, that they're more prepared for senior football, hopefully internally. But of course, it's not going to be everybody, so that could be an external opportunity as well. But no matter what, our aim as a staffing set is to make sure that they leave here better prepared for that, and then we have individual development plans for all the players so we can make the different tweaks, the different nuances, just to ensure that we're meeting the individual needs of all the players.
STF: You and the Timbers2 program serve as a bridge for many, connecting the gap between academy and first team football. How do you work together with the academy and first team staff to ensure players are reaching their maximum potential?
Jack Cassidy: Just communication, I would say. Phil's been really good with me, just in terms of initially welcoming me to the club. Then went away with the first team. When I first arrived in the country, I was in Orange County for a few days, which then enabled me to establish really good relationships with all the first team staff. So then that made it really easy. And then I worked closely with Darren from the under-eighteens, just to make the transition between those players nice and easy. So I just think the more communication, the better that we have.
I think if it's better to over-communicate than under-communicate. So it's just making sure that, for example, if we're taking under-18s players, and they're going to be in our roster, but they might not start for us. Are we having conversations to make sure they're getting enough minutes for the under eighteens? And the same goes when I'm communicating with Phil, because obviously the likes of Gage [Guerra] and Sawyer [Jura] have got minutes with us when they haven't maybe got the minutes that they desired with the first team. So we just communicate regularly on these things just to make sure that the players are getting the best program possible.
STF: You're coming from Europe and the Middle East into MLS NEXT Pro. What surprised you most about the American development ecosystem compared to what you've seen elsewhere?
Jack Cassidy: To be honest, I wouldn't say it surprised me, because I don't tend to have a bias about different countries or underestimate the quality in different countries. But the level of the [MLS] Next Pro league is good. There are some really good young players, both here and elsewhere, when we're playing against different opponents. And I just think maybe due to the distance in terms of where the United States is on the map. Sometimes that might be slightly undervalued by people looking from afar in Europe, but it certainly wasn't something that I underestimated before I came.
STF: Finally, overseeing the program bridging youth and professional football within the Timbers organization is a unique opportunity for a coach in terms of club development. For supporters who haven’t come out to see T2 play, and it should be said that home matches are free to watch at Providence Park, what should they expect from your team?
Jack Cassidy: I think what we've seen so far is that we're an extremely hard-working team. I think that's the element that's pleased me the most. I think it's an element that gets slightly undervalued. I think that in Academy and development football, there can be such a large emphasis on tactical development that we sometimes forget that you have to run, you have to work hard, you have to do all the things that a first-team manager would want you to do in order to get into his team. And that's something that I think the players are brought into terrifically.
There's a great shot in terms of video, right at the end of our game on Sunday, where Alex Bamford blocks a shot in, like the last kick of the game, we're already three nil up, and that desire, and then the final whistle goes straight away after that, and you've got five, six players just collapsing to the floor just through exhaustion. And I think like that, that we pretty much played that to the players today. I think that captures exactly how we've approached these first seven games, and it's something that we won't let up on.
We speak about performances a lot, rather than the outcome of matches. And I think we can always, you can't always control the outcome of a football match, because you've got referee decisions, you've got the bounce of the ball one way. Bounce the ball the other way, but we can control how hard we work, and we have certain metrics, which we call our world-class basics, and we aim to beat the opponent on those metrics every single game, and that's what we focus on. And I think that's a brilliant starting point for young players, because young players now, they can have all the ability in the world, but if they're not going to do the basic things, well, they won't get anywhere near first team football, not for a sustained career, anyway, and that's from my experiences, and that's something that the players have probably got, got on repeat in their head already, even after three months.
