The Cubs took another big step in their lengthy rebuilding plan yesterday, reportedly signing first baseman Anthony Rizzo to a seven-year, $41 million extension that could keep the 23-year-old in Chicago blue until 2021.

While there is of course some risk involved for the team here, reporters, analysts and fans have been largely supportive of the deal, praising the Cubs for locking up a core young player at a time when fewer and fewer stars are reaching free agency. And even if Rizzo tanks and his best days are behind him (which is unlikely), $41 million over seven years is a loss the Cubs can absorb with ease.

Anthony Rizzo: the one who got away. Photo by Kelly O'Connor,

Anthony Rizzo: the one who got away. Photo by Kelly O’Connor,

You can argue that the connection to the Red Sox here is somewhat tenuous, but I disagree. Rizzo used to be a Red Sox prospect. The men who just signed Rizzo to an extension, Theo Epstein and Jed Hoyer, have both played integral parts in Rizzo’s career to this point as well, holding positions in Boston, San Diego and Chicago: the three
organizations in which Rizzo has played.

But in a more abstract way, this deal is important to the Red Sox because it represents something they no longer have: young players worth locking up to long-term deals.

It’s easy to criticize trade that sent Rizzo, Casey Kelly and Reymond Fuentes to San Diego for Adrian Gonzalez in 2010. In some other ways, it’s easy to dismiss it, as the Red Sox have been freed from the burden of A-Gon’s contract. I don’t think either approach is right.

The Red Sox gave Gonzalez a seven-year, $154 million deal before the 2011 season: a potentially disastrous contract given that it’s now at least reasonable to question whether Gonzalez’ best days are behind him. There’s a temptation to say “no harm, no foul” since the Sox are no longer on the hook for that money, and since the talent we received in return for A-Gon – Allen Webster and Rubby De La Rosa – is pretty remarkable. But you can’t sign players to bad deals and assume you’ll be able to trade them later. Epstein and the Red Sox should not get a pass for the deal.

It’s also easy to shrug the trade off since Kelly hasn’t developed as expected, Fuentes is basically a non-prospect at this point and Rizzo was flipped to the Cubs for Andrew Cashner in what looks like a legendary head-scratcher. But this isn’t right either: Perhaps the Sox knew things about Kelly or Fuentes that led them to view such players as expendable, but without evidence that’s a tough argument to make.

I’m not trying to suggest that the Red Sox should not have pulled the trigger on the A-Gon trade: I loved the move at the time, and I thought A-Gon would be the next great hitter to anchor the Sox lineup. What I am trying to point out, though, is that it’s been quite a while since the Red Sox have developed and retained a young player who looks like he’ll be a difference-maker for a long time, and that is not a good thing.

The Red Sox do not currently have a player of Rizzo’s caliber to whom offering a Rizzo-like extension is even close to reasonable. Dustin Pedroia, Jacoby Ellsbury and Will Middlebrooks are the only offensive starters who are home grown, and the first two are not at analogous points in their careers with Rizzo. Pedroia once signed a team-friendly long-term deal, and we’ve been reaping the rewards ever since. Ellsbury did not, and it’s likely we’ll need to see him play for someone else in 2014. Middlebrooks is the closest thing the Sox have to a Rizzo-like player, but we need to see if he can make adjustments before cementing him as a big part of Boston’s future.

Deals of this nature for pitchers are even riskier than for their position-playing counterparts, but the Red Sox don’t have a strong fit there either. FelixDoubront is in some ways the pitcher equivalent of WMB – talented but clearly flawed – and isn’t worth the gamble. The other four starters in Boston’s rotation are older, and Webster hasn’t done enough to prove he should stick in the rotation, never mind deserve an extension. Your mind might jump to the likes of Junichi Tazawa or Andrew Bailey, but long extensions for relievers of any kind – never mind injury prone or non-elite ones – are never a good idea.

If we revisit this conversation in a year, we could be looking at a few more reasonable candidates – I’m looking at you, Xander, and you, Jackie – but we’re getting ahead of ourselves there.

The Red Sox have a ton of money to play with after dealing A-Gon, Carl Crawford and Josh Beckett (and Nick Punto) to the Dodgers last season, but we’ll likely find ourselves in a similar hole if we continue to use all that cash on older free agents. I have no problem with the strategy the Sox took this offseason, as they didn’t give out any deals that compromise the long term financial stability of the organization. But such an approach can only work for so long.

We’re getting close to having a crop of young players worth locking up for a long time again, and breaking up that crop is a mistake. My hope is that Rizzo’s deal can serve as a reminder of that to those who are growing impatient.