Root, Root, Root Against the Home Team

Still, none of it compared with the cash Epstein sunk into draft bonuses—a trend that started, it’s worth noting, only after Epstein ran off in a gorilla suit following the 2005 season, before returning a few months later with the promise of more power. Consider the case of Will Middlebrooks. Before he was Boston’s starting third baseman, the pride of Texarkana planned to be Texas A & M’s quarterback. So Middlebrooks, whom Baseball America labeled a “borderline first-rounder,” fell to the fifth round—where the Red Sox grabbed him and gave him $925,000 to ditch the pads. That was roughly “slot” money for someone drafted in the second round. But Boston paid it to Middlebrooks—and thus bought an additional elite prospect.

If you break Boston’s drafts down by signing bonuses, you’ll see the team repeatedly went over slot to turn cash into extra talent. In 2006 the Sox gave top-tier money to Ryan Kalish (ninth round) and Lars Anderson (18th round). In 2007 it was Middlebrooks and Drake Britton (23rd round). In 2008 it was Ryan Westmoreland (fifth round), Ryan Lavarnway (sixth round), and so many others that Boston became the first team in baseball history to dole out $10 million in a single draft.

Going over slot allowed the Sox to contend every year and to continue grabbing extra bigtime prospects. Some grew into good players. Others grew into trade bait. (Anthony Rizzo and Casey Kelly, the key pieces in the Adrian Gonzalez trade, both signed over slot.) Others, of course, flopped. But that was largely the point: The Sox used their money to amass as much talent as possible. The draft is baseball’s biggest raffle, and Boston always made sure to buy extra tickets.

Then Selig shut the party down. Under baseball’s latest collective bargaining agreement, which went into effect shortly after Epstein left for Chicago, the slotting rules come with actual bite. Each team, depending on the number and order of its picks, receives a set pool of money to spend on bonuses. If the Sox, for example, go just 10 percent over their pool, they now pay a hefty fine and forfeit future first- and second-round picks. In previous years, the team went about 100 percent over that figure. Put another way: If these rules had existed a few years earlier, there would be no Will Middlebrooks in Boston.

That’s a scary thought for a team in need of stars. Pedroia’s slugging percentage has declined for the past two years—which is exactly what you’d expect from a guy who turns 30 this season. David Ortiz is old and injury prone. Ellsbury is young and injury prone. And after the Carl Crawford fiasco, the team seems skittish about pursuing elite free agents. Besides, signing one could be counterproductive because, by league rules, it would most likely require surrendering a first-round pick to the player’s old team.

Boston’s farm teams don’t offer much hope, either. Minor-league experts rank the system as high as ninth and as low as 17th, but most agree that it’s heavy on solid, middle-of-the-road prospects but light on blue-chip talent. Keith Law, an ESPN analyst, sees only one potential superstar in the mix: the slugging shortstop Xander Bogaerts. “That’s a guy you build around,” he says, adding, “That’s the only guy in their system I see that way.”

A lack of stars, an increasingly suspect free-agent market, a more treacherous draft: In many ways, the future looks bleak in Boston. Which brings us back to tanking. This off-season, GM Ben Cherington spent more than $100 million on seven veteran free agents, each more of a solid contributor than a star. The moves felt straight out of Epstein’s early tenure. But this year’s Red Sox don’t need role players like Bill Mueller—they need studs like Manny Ramirez. Indeed, the team resembles the farm system: mired in the middle of the pack.

That’s why the Sox should have aimed for last place. Winning 85 games won’t make a big difference, but winning 65—and, more important, losing 97—just might. The Sox would secure a top-10 pick, boosting their chances at a star. They’d also get a bigger draft-bonus pool, allowing them to splurge throughout. They’d buy another year for players like Bogaerts to develop. And thanks to another quirk in the collective bargaining agreement—that the teams who pick in the top 10 can sign top free agents without forfeiting a first-round pick—they’d be free to sign new stars in the off-season.

But long-term planning has always been a hard sell in Boston. What Civil War general does Cherington compare to? Well, increasingly, he’s looking like an aide-de-camp. It’s an open secret that ownership overruled him in choosing Bobby Valentine as manager. The off-season spree feels equally top-down. Superficially, the direction has changed, from sexy guys (“Get me Carl Crawford!”) to scrappy underdogs (“Get me Jonny Gomes!”). But both seem driven more by worries about brand management and NESN viewers than by smart baseball strategy.

The owners’ obsession with today over tomorrow is exactly what drove Epstein out the door. But to return to the top, the Red Sox need at least one more year at the bottom. And the thing is, last year was so miserable that fans would have understood. Instead, it looks like the team has targeted 85 wins and, hopefully, an uptick in ratings. Hey, maybe the Sox will luck into a wildcard. But does anyone believe this squad can go all the way? And isn’t the only thing worse than not making the playoffs thinking that making the playoffs is good enough?