The Red Sox are a big problem

As nice as it was to watch Steve Pearce, a largely overlooked career journeyman, win World Series MVP, and David Price, a lovable personality attached to an unfortunate narrative, finally exorcise his playoff demons, the Red Sox are not our friends. Watching them win, even if the team features likeable players, is shitty.

This year’s Red Sox team was particularly impressive, there’s no doubt about that. They won 108 games, only eight wins shy of the 2001 Mariners and 1906 Cubs’ Major League Baseball record. They then went on to dominate the Yankees, Astros, and Dodgers, three strong teams in the own right, bombing through the playoffs with just three losses.

Once upon a time, the Red Sox were just lovable losers plagued by a horrid curse. Now that they’ve won the World Series four times in the past decade-and-a-half, they’ve become one of the most spoiled franchises in baseball. They feature a good scouting and developmental system and they have the cash to augment their core with elite talent and the ability to sweep their mistakes under the rug.

You might look at their roster, their group of impending free agents, and their mediocre prospect pool and think “this window is going to close right away” but the Red Sox of routinely navigated in and out of contention windows.

When the Red Sox won their second World Series of this era in 2007, they did so with a fairly different group than they did when they broke their curse in 2004. They had a few returning veterans like David Ortiz, Manny Ramirez, Jason Varitek, and Curt Schilling, some new talent acquired in high-profile trades and signings, like Josh Beckett, Daisuke Matsuzaka, and J.D. Drew, AND young internally developed players like Dustin Pedroia, Jacoby Ellsbury, and Jonathan Papelbon.

When they won in 2013, they did so after completely falling on their face. Soon after the Boston Globe infamously called the Sox who had recently acquired marquee players Adrian Gonzalez and Carl Crawford the greatest team of all time, the Bobby Valentine-led Red Sox imploded to a 69-win season. The next year, though, they won it all with John Farrell at the helm along with a rag-tag bunch of overachievers.

They went all-in again after that, adding marquee free agents Hanley Ramirez and Pablo Sandoval. The signings fell flat, but the Sox boasted enough financial wiggle room to sweep both under the rug, opening up room for more big acquisitions like J.D. Martinez, David Price, Chris Sale, and Craig Kimbrel. Then, in 2018, they won with a new crop of drafted-and-developed players like Mookie Betts, Xander Bogaerts, and Andrew Benintendi.

In the next couple years, Betts, Benintendi, and Bogaerts’ cheap years will come to an end, and Kimbrel and Sale will be able to hit the open market. The one saving grace Red Sox opposers have is the fact Dave Dombroski, an executive notorious for selling the farm to be good right now, is at the helm of the organization. Boston’s four championship teams are the blueprint of Theo Espstein, now with the Cubs, and Ben Cherington, now with the Blue Jays. Still, it’s easier to imagine the Sox jumping from this window to the next with some new crop of internally developed players, a few hold over veterans from the previous window, and a bunch of huge free agent adds.

None of what I’m saying should be new to anybody. Everyone knows the Red Sox have been very good over the past decade-and-a-half. Still, it’s a frustrating prospect for fans of the Blue Jays as we wait for our contention window with Vlad Jr. to finally open knowing full well that the Sox (and, duh, the Yankees, but I don’t even want to go there right now) aren’t going to make it easy.