Dave Dombrowski and the Dangers of Free Agency

There’s a scene in the movie The Princess Bride that involves the Sicilian criminal genius Vizzini, who has captured the princess and Dread Pirate Roberts who hopes to save her. In a battle of wits to the death, Roberts puts deadly iocane powder into one of two glasses of wine. Then, he asks Vizzini to deduce which is the safe glass and drink it while Roberts drinks the other. Vizzini complies and they both drink. Vizzini falls dead. The princess asks Roberts how he knew Vizzini would pick the wrong glass. He says he didn’t know. He poisoned both glasses because he’s immune to iocane powder.

The baseball season is over, and as it falls into history, the new season steps forward to take its place. This process is essentially instantaneous. The Red Sox went from nothing during the playoffs and World Series to the center of the baseball world in a single click of a second hand. Boston is in the unique position of having a stacked farm system, a talent-laden roster, and a GM who had no part in assembling any of it. As such, he’s not nearly as attached to the players in Boston now, thus making it much easier for him to make them players who used to be in Boston. Dave Dombrowski is here to shake things up.

While there is likely to be much wheeling and dealing, the free agent market hangs over Boston’s head like an axe at a beheading. The reason is simple: the last two Red Sox general managers (generals manager?) lost their job due to their failures in the market.

In 2011 John Lackey was coming off his first season in Boston, a 2010 season that saw him throw 215 innings of 4.40 ERA baseball. His strikeouts dipped and his walks jumped. But improvement was expected! It was then not delivered. In fact, Lackey was even worse, throwing 160 innings with an ERA of 6.41 before getting shut down for Tommy John surgery. Lackey had been GM Theo Epstein’s big addition to the pitching staff and now it looked like the Red Sox would pay Lackey three seasons worth of top-of-the-rotation money for a bit under two seasons of awful pitching. What’s more, had Lackey been anywhere near good the Red Sox would have made the playoffs instead of missing in excruciating fashion on the last day of the season.

Then there was Carl Crawford. Crawford showed up to Boston with a new seven year $142 million contract having forgotten how to hit and field. In April Crawford hit .155/.204/.227 and there was no looking back. He wasn’t exactly horrible with the bat after that though he wasn’t fantastic either, but he the overall appearance was a shell of the player who had played All Star-caliber baseball in Tampa just the season before. This was Theo Epstein’s big addition to the offense. Then Crawford got hurt, which, purely from an on-field standpoint, was probably for the best. It was those failures along with some others that signaled the end of Epstein’s time in Boston and with him fellow 2004 hero manager Terry Francona.

Epstein was the GM who had ended the curse not once, but twice. He’d bested the Yankees, he’d built the team and franchise he’d set out to build, and he’d made the Red Sox the greatest organization in baseball from the time he’d taken over to then. But after Crawford and Lackey showed up and sucked horribly, he was gone. That’s a bit of a simplification of course, but it’s roughly correct. Without Epstein’s failures in the free agent market, it’s entirely possible he might still be here.

Time waits for nobody, and in fact, it speeds up like hell when you’re a GM who just gave $90 million to a guy who can’t hit or field.

But he left and was replaced by assistant GM Ben Cherington. Cherington’s Red Sox finished in last place in his first season in charge. Then he hit the market hard. He brought in Stephen Drew, Mike Napoli, Jonny Gomes, Shane Victorino, Mike Carp, David Ross, Ryan Dempster, and Koji Uehara. That team won the World Series. Cherington didn’t hit fully on each player, but he got something productive out of each, and in the world of free agency that’s no sure thing. Cherington had turned to the market, supplemented the talent on hand with free agents, and won a World Series. Then 2014 happened and the team failed on the field once again.

Following that failure, for the 2015 season, Cherington decided he needed to upgrade the talent on hand. He went back to the free agent market to bring in Hanley Ramirez, Pablo Sandoval and Justin Masterson. As it turned out, all were horrific failures on a scale that seemingly couldn’t be predicted (maybe Masterson could have). The team cut Masterson mid-season but Sandoval and Ramirez were and are on long term contracts. And they were and are both awful. And the Red Sox finished last again. And that was it, the GM lost his job. Again. Less than two seasons removed from mastering the market and winning a World Series, Cherington had been given the boot hard.

Like Epstein before him, that was it. Unlike Epstein, there wasn’t really any other reason. Epstein squabbled with team president Larry Lucchino, had recently failed in the draft, and a few of his contract extensions were looking like expensive busts. Cherington had no such baggage. He was put out on his backside mostly because Pablo Sandoval went from above average hitter and above average fielder to downright awful at both as soon as he put on a Red Sox uniform. Hanley Ramirez, beyond April when he crushed homer after homer, stopped hitting and put on a display of fielding in left that would make little league teams look away.

Over the next few weeks and months you’re going to hear the Red Sox connected with just about every free agent there is. There will be David Price rumors, Zack Greinke meetings, Johnny Cueto whisperings, anonymous mentions of Jordan Zimmermann, and outright discussions of Chris Davis, Darren O’Day, and anyone else who plays baseball and has no contract. Dombrowski has his preferences and he will try to remake Boston’s roster in that image over the off-season and as he’s already said, that image includes a top-of-the-rotation starting pitcher. He may want to upgrade the offense with something more certain at first base than Hanley Ramirez, who it just seems like the Red Sox would rather pay to explore water on Mars than to play first base for them next season. It’s possible Dombrowski can do all this through trades but that seems unlikely. He’s probably going to have to sign a free agent or two. Or six.

If Dombrowski is going to give $200 million to David Price or $150 million to Johnny Cueto or whoever or whatever, he had better be certain. No, scratch that. He’d better be whatever word means three times the power of ‘certain’ before doing so. He just got here, and guys who just arrived typically get some time before being held to the fire, but Ben Cherington won a World Series two years ago. Two years ago! Two! And he’s now a visiting professor at Columbia University. Time waits for nobody, and in fact, it speeds up like hell when you’re a GM who just gave $90 million to a guy who can’t hit or field.

If Dombrowski wants to remake the roster and win now at the expense of tomorrow, he’d better be sure about the choices he makes when it comes to free agents. What I’m saying is Dave Dombrowski had better be immune to iocane powder.

Photo by Mark L. Baer/USA Today Sports Images