Pedroia signed a long term deal that bought out free agent years. Bogaerts signed one also, unfortunately one that required an opt-out that he's going to exercise. I don't think the Sox have had any different luck when it comes to locking in home grown guys than other teams (is Judge really that much different a case from Betts or Devers?). We might just be a little too close to things being Sox fans that our perspective is off.
The deck is already tilted in the team's favor with young players since they come up essentially signed to dirt-cheap 6-7 year deals. There isn't a great ton of benefit to be realized for teams to lock in a young player beyond those seasons, especially early on. They might get cost-certainty (relative to going year-by-year in arbitration) but all the risk is on the team's side. It's a delicate balance to find a deal that somewhat mitigates the risk while also enticing a player to forego or delay free agency where they could earn (potentially a lot) more. Unsurprisingly, long term deals to pre-arb guys remain the exception rather than the rule.
