For all the good Henry has done for the sox, his desire to spend has been somewhat mercurial.
When Cherington took over, he was not allowed to spend. He had to trade Marco Scutaro just so he could bring in Cody Ross. That's a small market maneuver. Then he was allowed to spend and he went nuts with a massive spress that worked out really well (meaning we won a WS) when he brought in Napoli, Dempster, Drew, Victorino and (especially) Uehara. And then he spent poorly again with Sandoval, Hanley and Rusney. And he was not allowed to spend again - remember "no long term contracts for pitchers" - so Lester and Lackey were dealt.
Dombrowski was in the opposite camp. He was allowed to spend like mad, basically an open check book. He also lived up to his rep as a Farm Killer. And it worked for a while. But when it stopped, so did his ability to spend.
And then Bloom was brought in and was allowed to spend on some second tier players like Perez and Peraza, but nothing else.
It's like when the Sox win, Henry laments how much it costs to do so and dials back. But then realizes the losses are even worse when the Sox lose. And then he forgets all about this. Lather. Rinse. Repeat....