How Theo Epstein Can Learn from Peter Chiarelli and the Boston Bruins

They play in buildings separated by less than three miles, but in terms of their general managers’ attitudes to free agents, the Red Sox and Bruins are worlds apart.

In the last few years, while the Red Sox have waved goodbye to players who reach free agency, the Bruins have given them shiny new deals and extensions.

The Bruins were never renowned for being big spenders. Quite the opposite, in fact, with many blaming the team’s reluctance to bring in more big players for their Stanley Cup drought.

When the NHL introduced a salary cap five years ago, however, that changed. The Bruins have been near the cap every year, and it is difficult to call a team like that "cheap."

One gets the feeling the B’s are close to reaching the Stanley Cup Finals and just need that little spark to send them there, be that a big acquisition, a Hart Trophy-calibre season from someone or a stroke of luck.

Over in the Back Bay, one is not instilled with the same optimism. Only four hitters who were starters for the 2007 World Series campaign remain so, and it is possible the team will be almost unrecognisable when they open the 2011 season in April. This is because it is difficult to see GM Theo Epstein bringing back the players who are already on their way to Logan Airport.

Some examples of this are obvious. Johnny Damon is, naturally, top of the list (although it is impossible to outbid the Yankees), and four years later Jason Bay followed a similar path to the Empire State.

Alex Gonzalez left Fenway Park without a new deal twice in four years, when Epstein should have been begging him to stay after his first stint in Boston.

Entering this offseason, the general assumptions about the fate of many players speak volumes about public perception of Epstein’s attitude to free agents.

Victor Martinez, Jason Varitek, Adrian Beltre, and David Ortiz could have played their final game in a Red Sox uniform. They all should be brought back.

The Red Sox will probably pick up Ortiz’s $12m club option, and then, barring another monster year, he’ll be gone.

As for the other three, chances are they’ll leave—or, more accurately, be allowed to leave. Martinez was offended by the Red Sox’ first offer, and Beltre will command a huge contract after his offensive resurgence in 2010.

Epstein may stun everyone and bring both Martinez and Beltre back, but it would be staggering given the precedent he has set.

Of course, there is one noticeable exception to all this, and it's one Epstein probably already regrets.

Josh Beckett was given a very handsome extension in April, at four years and $68 million. In return, he gave the Red Sox the worst season of his career. Beckett does have a tendency to alternate good and bad years, however, so it’s not fair to judge the deal just yet. It doesn’t look good, though.

It may all work out for the Sox, and everyone might feel good about a return to the playoffs when spring training rolls around. Right now, however, it is far easier to get excited about the structure of the Bruins.

That is because the front office realises that if you are to compete in a conference which houses Sidney Crosby, Alex Ovechkin and Nicklas Bäckström, you need to keep your best players.

Captain Zdeno Chara was signed to a new seven-year contract extension, keeping him in the black and gold until he’s 40. Seven years is a long time, especially for someone who has been around a while, and he might well have signed for five years, so at first glance, the contract is a touch scary.

However, he’ll make $6.9 million for six of those years and $4m for one, a substantial drop from the $7.5 he will make this season.

Patrice Bergeron’s new deal (three years, $15 million) will only bump his cap hit by a quarter of a million a year and safeguard against his demanding a big contract, or leaving entirely, should he have a career year in 2010-11.

This year will see Milan Lucic’s extension kick in too. He is the fourth biggest dollar sign against the cap, at a tick over $4 million, behind Chara, Tim Thomas and Bergeron. Also, he scored only 20 points last season.

Bear in mind, however, that he missed over 30 games and was immense in the playoffs. The way he can play at times, four million for Lucic is more than acceptable.

Not that GM Peter Chiarelli has gone mistake-free. The Thomas contract was a poor decision. His cap hit is $5 million this year, which is simply ludicrous for an ageing second-string goaltender.

The Beckett contract feels oddly similar, but one can only hope it does not follow the same path.

Looking at both teams, one would be hard pushed to claim the Red Sox were better prepared for a title run any time soon. They have great young talent in the minors in Lars Anderson, Josh Reddick, Ryan Kalish and Casey Kelly, but a lineup of rookies and minor leaguers failed to beat the Yankees and Rays this season; it will be no different in 2011 if Epstein doesn’t strengthen this team with free agents.

He should look at Chiarelli and the Bruins.

The Boston Bruins are built for the future. One can only pray it’s a future that eventually sees Chara lifting the Stanley Cup.