To give context to Sylar's point Ramsey's contract at Juventus is worth £400k a week and he received a £8m signing on bonus. He basically got to absorb most of the transfer fee the club would receive if they sold him under contract into his wages.
If Spurs try to push Rose to sign for a club they want to sell him to his contract negotiating position is severely weakened.
If he leaves on a free he's in complete control to cash out in a big way or play for a club that appeals to him lifestyle wise or ideologically.
I understand the principle of that, but doesn't Rose's age of his contract being up throw a big spanner works there from his side of things?
If Juventus wanted to buy a 28 year-old midfielder with Ramsey's ability he's probably going to cost a bit so they might think they're better off, or at least no worse off by going for him and giving him the money they would otherwise have paid as a fee for a different but similar player.
What do 31-year old full backs go for? I'd say little to nothing so it could make it quite different. He'll have absolutely no re-sale value (not that Ramsey will have much either in his example). We also know that clubs are often reluctant to offer anyone over the age of 30 more than a 1 year extension because they fear them suddenly declining so in theory the same should apply for offering over 30s fat contracts when you sign them on a free.
It could work out for him financially, but I think it's a bigger risk from his from perspective than Ramsey if that's a big consideration for him.
Edit:
Just pulling some numbers from my backside, so not about Rose as such:
-Player is 29, has 2 years of his contract left at £100k/week
-A team wants to buy him, would offer £150k/week on a 4 year deal
- If he stayed and left on a free he'd need to be offered a £200k/week 2-year deal at 31 to equal what he'd have got in total if he left now, and more than £200k/week if he wants to come out on top - might be a bit much for interested parties?
Signing bonuses not included in the above.
