Personally, since Tony is older, his window to earn money is smaller than Ishe, Peter and Jesse's window.Add to that the fact that Tony is not married and does not have a wife that has an option to work if needed.
There is a possibility that they could dissolve the teams in the second round and have challenges that could be won by one single fighter who could in turn box anyone they wish.
If you figure that two of Jimmy, Tarick, Joey, and Juan are going to make the second round, Tony could beat any of them. Tony would love to have the chance to beat Peter (since the fight will be on neutral ground) but I doubt he could do it.
Realistically, Tony could easily beat 2 of the 7 other fighters in the 2nd round. If each fighter wins the challenges for himself, Ishe, Jesse, and Alphonso couldn't "throw" a challenge. They would need to compete. Jimmy, Tarick, Joey or Juan may actually WANT to fight Tony in the 2nd round since they wouldn't have a prayer against any of the "Big 4".