The Boston Red Sox have baseball’s best offense. They’re deadly. They’re even more deadly at home, though, where their right-handed sluggers can take aim at the Green Monster. And they’re at their most deadly when facing a left-handed pitcher at home. Jonny Gomes, Will Middlebrooks, Jarrod Saltalamacchia and Mike Napoli have big, ugly strikeout rates against right-handed pitching, nearly 30 percent in composite. Since none of Boston’s big lefty bats have a similar split problem, the net value equation favors the Red Sox when a southpaw gets the ball.

The Tampa Bay Rays didn’t have a good way to get around sending two lefties to the mound in Boston to kick off the American League Division Series. Alex Cobb pitched the Coin Flip Game against the Cleveland Indians Wednesday, and while neither Chris Archer nor Jeremy Hellickson is inviable as a playoff starter, there’s a clear difference in overall quality between either and Matt Moore–and an even clearer difference between any of those three and David Price. The differences likely overwhelmed matchup considerations.

Price and Moore needed to be the guys, then. That was a fairly easy decision, though not an enviable predicament.

What was interesting, and disappointing, was the degree to which Joe Maddon entrusted (or attempted to entrust) those two games to those two guys. Maddon, the master tactician, aggressive handler of the entire roster and consummate manager of egos (even when he can’t stroke them), basically took the Rays out of the first two games of a best-of-five series.

The most common error smart people make when talking about managers is to understate the positive impact skippers can have, and focus solely (or very heavily) on the ways they appear to take runs or wins away from their teams. The second-most common is to underexpect mistakes, even large ones, by good managers.

I feel like the latter error has infected me when it comes to Maddon. I really found myself slack-jawed when Maddon failed to relieve Matt Moore either during or after the fourth inning Friday in Boston. I couldn’t believe he didn’t rush a short reliever into the game to get out of what became a five-run bottom of the fourth. I couldn’t believe Moore then got to face four more batters (groundout, double, intentional walk, double) before Maddon got him out of there in the fifth.

Eight runs hit the board, and the game was over. A 2-0 lead turned into an 8-2 deficit in the time it took Moore to record four outs. That was 14 Red Sox batters. Given the short leash a lefty should be on at Fenway, in October, when every game is a must-win, Moore should have faced no more than seven of those 14 batters. The game got away from the Rays, and it was primarily Maddon’s fault.

I’m not sure whether to castigate Maddon more or less for Saturday night. I can tell you, though, that he didn’t go wrong by leaving David Price in to face David Ortiz to lead off the bottom of the eighth. That decision turned out badly, and made the mismanagement glaring, but the mistake was letting Price take the mound for the bottom of the fourth frame.

Price had surrendered five hits through three, including two doubles and a home run. It was 4-1 Red Sox. Boston had Napoli, Gomes and Middlebrooks due up in the fourth—the bulk of the bunch who are so vulnerable to tough right-hander. That was Maddon’s chance to keep a lid on the game, to give Tampa its chance to get back into it. Instead, the Sox added single runs in each of the fourth and fifth innings, on two walks, a triple, a double and a single. The Rays scored two in the fifth and one in the sixth, but never did catch up.

Now, Maddon should have made these moves. I was yelling at my phone (the At Bat app lets you listen to even post-season games, live and streaming; it’s wonderful and you should buy it) even as those things were happening, so I can say that Maddon erred without the mitigation of hindsight bias. That said, though, I will offer this as a qualifier to my criticism: Maddon was in a nearly impossible position for the modern manager.

Quick hooks, as most of the game’s great managers understood them, are dead. Fifty years ago, one of every six starts ended before the starting hurler recorded a tenth out. Over the last few, it’s one in 20. (See The Hardball Times Baseball Annual 2012, “Quick and Slow Hooks,” by Chris Jaffe, for more.) The days of starts shortened by signs of ineffectiveness, even in high-leverage situations, are over. While the roster compression and schedule easing that takes place in October should and do make managers slightly more aggressive, no one pulls their starter if four of the first seven batters reach base anymore. It’s just not the way it works, and in some cases, that’s to the good.

Most of the time, though, it’s to the bad. That’s because the effort to get guys through innings, to squeeze a bit more out of him, is not the product of design, but of desperation. Roster management has gone far off the rails. Teams are committed to full five-man rotations, which disallows bringing a short-hooked starter back on short rest in most cases. Teams are loaded with short relievers—WAY TOO MANY short relievers—and have narrowed the role of relief pitchers until the long guys necessary to execute a short-hook strategy are virtually extinct. Teams refuse to let starters who are cruising, pitching really, really well, finish or try to finish outings.

We often say, and it’s often true, that a manager did not put a certain player in a position to succeed. We sometimes say, although less often, that a front office put a manager in a position to fail. In this case, 40 years of poor roster construction, devolving pitching strategy and bad managing put Joe Maddon against the wall. He still made the mistakes of inaction, but it’s not fair to discuss them without noting that he had few good alternatives, or at least few realistic ones. Because teams greedily bought into a bubble market when it came to building, acquiring and using relievers, Joe Maddon, baseball’s best active manager, basically shredded his team’s chances of advancing any deeper into October.