From homeless to pro football: What happens to the guys who never quite make it?
In an effort to land a look by an NFL team, he slept on a mattress outside of a community center, had no money, and lied his way into the tryout.
You always hear about the athlete, or entertainer, who sleeps in their car, or eats the leftovers behind the restaurant in the alley, before catching the break to realize their dream. You never hear about the people who do the same things but never reach that status.
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There are far more examples of those.
Damon Sheehy-Guiseppi is not a wide receiver you'd know. You may have heard his story as the guy who was 'homeless' before he caught on for hot minute with the Cleveland Browns, when he was 21. That was in 2019.
Today, Sheehy-Guiseppi is 30, and just completed the season with the UFL's Arlington Renegades, who missed the playoffs.
Considering where Sheehy-Guiseppi began, he should never have played a game beyond unior college. He can always say he made it as a pro football player. He was paid, and sometimes housed, to play football. It just wasn't in the NFL.
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Whether this qualifies as 'success,' or a dream fulfilled, depends not on the fan, coach, or scout but Sheehy-Guiseppi.
A high point in the football career of Damon Sheehy-Guiseppi (right) when he was with the Cleveland Browns during training camp in 2019. He just finished the season with the Arlington Renegades of the UFL.
Never quitting football
Sheehy-Guiseppi ran track in junior college before he transferred to another community college and tried out for the football team. In 2016, he was first team National Junior College Athletic Association All-American after he led the nation in kick return yards for Phoenix College.
This is the part how he became 'homeless.' After his college career ended following the '16 season, he was done with football before he decided to give it one more try. He had been given an address of an NFL free agent workout near Miami.
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'I saved enough money for a one-way ticket to Miami,' he told the Star-Telegram in an interview of his trip from Phoenix to South Beach in the spring of 2016. 'I didn't have a car. I had a cell phone. That was it.'
When he landed, he had no money. Someone spotted him at the bus stop outside the airport and gave him $5 for a one way ride that would drop him off about one mile from the facility.
When he arrived for the tryout, his name was not on an invite list with the approximately 15 other players. He knew one name to name drop his way into a workout. That part worked.
But he had no place to stay.
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'I found a Jewish Community Center that was gated, so my first night in town I found this little grass spot in the back and I thought, 'I'm going to stay here,'' he said. 'Then I found a mattress that was going in the trash. I dragged that over behind the bushes and trees. No one could see it.
'I made sure I woke up early enough to get my workout in. Then I would go to the beach. Go to a laundromat. Relax. I would just walk around with my duffle bag until it was time to lay down again.'
He ran into a familiar face at the tryout, who knew an agent, who took him to lunch. It was the first meal he ate since the Chex Mix on the plane. He ate, and took their to go boxes. Not entirely sure of the agent's intentions, he passed on the ride and instead had to call a friend in Phoenix to arrange a cab to the Jewish Community Center.
This was one week of his life, but it paid off when the Browns invited him for a tryout in Cleveland.
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No one ever caught him sleeping on that mattress behind the Jewish Community Center.
'Making it' in the pros
During his tryout with the Browns, he ran a 4.38 40-yard dash. That earned him an invite to training camp. He had turned a decimal point of an opportunity that he created by himself into a real look.
In the team's first preseason game of the 2019 season, he returned a punt 86 yards for a score. Less than a month later, he was cut.
'After that, it all gets a little blurry. I don't remember the teams but I remember the leagues,' he said. 'It was the XFL in 2020. Then it was off to The Spring League. ... I think, in all, it was 10 leagues.'
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Using Phoenix as his home base, where his mother lives, he never did stop chasing football. He signed to play with the XFL when it launched in 2020, but that ended a few months after it started because of COVID. 'The Spring League' was an actual developmental league, that folded in 2021.
He signed with the CFL but never played in a game because of injury. He signed, in 2022, with Major League Football, which closed during training camp.
Late in 2023, he signed with a team in Italy, and led his team the following year in receptions, yards and touchdown catches. He was named that league's offensive player of the year in 2024.
'Now that was super fun,' he said. 'It's the same game, but the speed of it was different.'
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After that season, he signed with the UFL for 2025, but battled injuries nearly that kept him on the sideline for most of the season.. He said playing for the Arlington Renegades is the most money he's made as a pro.
If someone had told him when he started this that he could be a pro football player, but that this is what being a 'pro player' is, would he do it?
'Tough question. I would do it because it's not over. So I feel like my end goal is still gonna happen,' said Sheehy-Guiseppi, who hopes to eventually work with young players to help them navigate a system that can crush them if they are not careful.
His end goal is one more try out. One more look by an NFL team.
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Whether it comes or not, Damon Sheehy-Guiseppi has had a career as a pro football player. He was paid to play football.
Not a lot, and it wasn't in the NFL. Whether this qualifies as 'success,' or a dream fulfilled, depends not on the fan, coach, or scout but Sheehy-Guiseppi.
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