Lets drop the "he downt wike da presha" argument. These guys are going to take money and yrs over environment and if its close, then they will go with the better environment for them.
Lets start with Holliday:
He turns 30 this offseason
His career line is .318/.387/.545 for a .932OPS
His 2009 line was .313/.394/.515 for a .909OPS
His 2009 line was brought down by a dismal experience in the expanse in Oakland while languishing in last place. Since being infused into a playoff race, he put up a .353/.419/.604 line for a 1.023OPS.
he can play both OF positions well (minus that one big error) and brings speed with his other skills (80SBs in 5 seasons).
So, this guy is a top tier performer who brings 5 tools to the table and is entering the prime of his career. The last guy with his resume at a young age to hit the market was Teixeira, and you saw what he fetched. JD Drew prior to his deal with Boston was a similar performer, albeit his exodus from the dodgers and his durability made his situation a bit more dicey.
Magglio Ordonez was also very similar when he signed, but durability was also an issue since he was coming off an experimental knee surgery. He signed for 5yr 75 mil with 2 options that will make it a 7yr 105mil contract, and both options are likely to vest.
So, if we consider JD Drew as the low point as Drew is the cheapest of the three and had issues come up on his physicial, then 5yrs 70 mil should be the low point. Then consider that Holliday will be younger than both Ordonez and Drew, AND he has much more speed and has no durability issues and you are probably looking at Ordonez's AAV being the minimum salary here.
Then consider one other confounder, the Soriano signing in 2006. He signed for 8yrs at 136mil at the same age. Now Soriano was more of a speed threat, but is much worse in the OF and has been a worse hitter (OPS wise) than Holliday.
So, where does that leave us? Tex is the better player when compared to Holliday mostly due to Tex's insane patience, better power, switch hitting, and age (he was a yr and a half younger at the time of his FA compared to Holliday's).
So maybe Tex's contract is a ceiling at 8yrs 180million dollars. I would say that JD Drew's 5yrs 70 mil is a starting point AAV wise. And Ordonez's 7yrs 105mil contract and Soriano's 8yr 136million dollar contract are good middle points. I would have to say that Boras is going to get 7 yrs out of someone with a likely vesting option for an 8th since he is only 29 (turns 30 in 3 months). So lets say that, to sign Holliday, the sox would need to offer 7yrs $112mil with a vesting option for 18 mil on yr 8. Would that be too much? Too little? I dunno, but that is where I put his figure at.