You should use Free Agency to build a Farm. Not to build a Major League Team year after year. Dodgers and Yanks have spent, but their Farms are some of the best in talent.
Our number 1 weakness is consistent Pitching talent in the lower levels. We had to flip our Positional Talent, for this glaring weakness.
If I was Henry, I would re-evaluate the whole Scouting Dept. They do not produce, in the most important Position in baseball, Pitching, and it's costing him, money and Prospects.
We've only hit the Tip of the Iceberg with the Yankees, I made sure to go to both Double AA Teams games, last year to compare the Sox and Yanks talent. It's not even close. Yanks got some talent coming up, and what's worst, their A+ Team was evaluated as the best in the Minors, at their level. These young arms are coming, and the Sox wont have the answer.....except money, and the few good Prospects we have.
This is the problem, going forward. Money, is money, easy to spend, hard to produce talent.