Boston Red Sox

In an exercise of reflection, chief baseball officer Chaim Bloom was asked to list one thing he regrets and one thing he's most proud of in his few years ...

I think we have a good team for 2023, a team that should be able to compete in our division, to make it to the postseason, and hopefully play deep into October. But the only way to do that is to have that talent coming through the pipeline.” Some have compared it to the team in 2013, when Cherington signed a bunch of veterans on short-term deals. “It doesn’t mean we’ll be right all the time,” Bloom said. Instead of hoping against hope now, as Red Sox fans did for 86 years, there seems to be, for at least the angriest fans, sadistic pessimism; it can feel satisfying to root against a team that surely won’t be good enough. The Red Sox signed David Price to the richest pitching deal in MLB history at the time, emptied the farm system for Craig Kimbrel and Chris Sale, and signed J.D. “In some ways,” said general manager Brian O’Halloran, a fixture in the front office through all four regimes. “And dating back to the beginning of this ownership group (in 2002), our goal from the very beginning was to build what Theo referred to as ‘The Scouting and Player Development Machine.’ We talk about it now, the pipeline of talent that comes through to form the core of your team. But I am proud we did that and I think I sleep better at night when I lead a decision-making process that results in us doing that. Taking flak isn’t new for leaders in the Red Sox front office. “There’s a ton of things in both categories,” Bloom said in a phone conversation this week. “I think we haven’t been afraid to do things that were controversial or might not make sense to people at first glance when we believed they were right.”