Picking up the option is EXACTLY the kind of mistake that this FO has typically avoided, and should avoid.
I think that Manny is frustrated because he thinks the team should show him "respect" and just pick up his option. The idea of making carefully considered, rational financial decisions is probably foreign to him...he's a flighty free spirit who has more money than he probably ever dreamed of and doesn't need to think carefully about what he does with it. He probably sees this primarily a personal issue...the team is dissing him by not picking up the option or signing a long term deal when he's playing well.
Boras is probably stirring the pot...he likes to take a hard line with teams and encourages his players to do so, and always emphasizes how valuable the talented players are to the teams. He's pushing to get Manny as much money as possible while he's still playing well, before decline really sets in.
I think that it's hurt that Ortiz has not been around, as well...I think that Papi helps keep Manny calmed down and under control a little more. They're good friends and Papi is a more reasonable and responsible person...any influence he has on Manny can only help.
If the BoSox pick up the option, they'll either be paying a lot for what will most likely be falling performance from Manny, or they'll eat a lot of that money in a trade. I think they need to punish him when he acts up and hold out the lure of picking up the option if he has an oustanding stretch run...and then say goodbye, unless he goes totally insane at the plate and hits .330 with 40 jacks. If Manny is able to force the team to do their bidding, they'll end up doing the same with other players down the road, and the team will be weaker.
I don't think that Holliday is a bad option for the future...overrated, but a decent hitter on the road, and Fenway is a nice place to hit, too. There might be better options, but I don't reject him out of hand as a Coors hitter. Lowell is a Fenway hitter, and we like him, right?
Dunn as a future option worries me a bit now...the plummeting average bothers me, but he is hitting a gob of jacks and still walking. I worry about him aging early and hitting .190 soon, though. I still like him more than JP does...