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The Punto/Mega-Trade: Lessons From An Un-Dead Theo Epstein

What if Theo Epstein came back from the afterlife (i.e. Chicago). What wisdom would he pass on to us about the Nick Punto Mega-Trade?


Anyone locked in the basement over the last six months is probably dead. But, if you got out, and are a Red Sox fan you'll probably be pretty shocked to hear about the huge trade the Red Sox pulled off with the Dodgers last August. That deal, for the benefit of you unfortunate basement-dwellers, sent Carl Crawford, Josh Beckett, Adrian Gonzalez, and its namesake, Nick Punto, to L.A. for some minor leaguers and the last gasp of James Loney's career.

There's a part of the deal that doesn't often get mentioned in recaps like the one above because recaps tend to focus on the big names, the star-quality players who were shipped across the country. The two minor league (ish) pitchers who came the other way (look out the window around Kansas and you'll probably see Josh Beckett waiving back) are easily forgotten. It's not that Rubby De La Rosa and Allen Webster were unimportant, but given the starpower and the sheer tonnage of the dollars involved, it's no shame that they got lost in the shuffle.

My perception of the trade was that it was primarily done for salary relief, to reload so to speak. The Red Sox were locked in with Carl Crawford and to a lesser extent with Josh Beckett. Adrian Gonzalez was the cost to wipe Beckett and Crawford's deals off the ledger, and Nick Punto came along for humor value. The Red Sox roster, for lack of a better term, wasn't working. They wanted to start over but they couldn't do it with because they were tied to these under-performing veterans on long term, expensive contracts.

Cut to yesterday. I was attempting to jog around my neighborhood, an event which probably looked more like an old, fat blogger in comically tight fitting clothes hobbling slowly down the sidewalk because that's what it was. To keep me motivated during these public ego flogging sessions I often listen to podcasts. BP's Effectively Wild is a favorite, but on that day I was listening to an interview Theo Epstein did with WEEI (you can find it here). One of the hosts -- it might have been Alex Speier -- asked Epstein about his reaction to the MegaTrade. Epstein said the following which I've transcribed so the wording might not be exactly correct.

So much was made of the players who went from Boston to L.A... but not enough was made of the young talent that came back... Webster and De La Rosa [were] the key to that deal. The payroll that [Boston] freed up was remarkable in it's own right. ...[but] having available dollars today with this market place dynamic is not what it was 10 years ago or 5 years ago. [With] payroll flexibility you could do just about anything you wanted to... These days with TV money and what's going on in the game, there are a lot of teams with money to spend and there are only so many ways to spend it. There's a lot of teams with money to spend and fewer quality free agents available. Just having money to spend doesn't put a franchise in a great position anymore. So I think the underrated part of that deal for the Red Sox was the young pitching coming back and I think it will serve them really well for a long time to come.

To specifically highlight the important point here: Epstein thought the deal that took a quarter billion dollars and 14 player seasons off Boston's books wasn't done for payroll flexibility, it was done for prospects. It was less a tacked on portion than a significant part of the deal.

While I was staggering down the street I thought about it. And he's probably right. A quarter billion dollars sounds like a lot of money and OK it is a lot of money, but in this marketplace a quarter billion spent over 14 seasons isn't going to buy the top talent anymore. This off-season the top starter on the market, Zack Greinke signed for six years, $147 million. That's an average annual value (AAV) of $24.5 million. The top hitter on the free agent market was Josh Hamilton. Many wondered about his (and Greinke's) off season issues and his (their) ability to play in big markets, yet Hamilton still hauled in a five year, $125 million deal, an AAV of $25 million. If Beckett, Crawford, and Gonzalez were the ages they were when they signed their most recent deals right now and were free agents to boot, they'd collectively get much more than a quarter billion. I'm not saying the contracts they signed with Boston are bargains, but if those guys perform up to code (something all of them were having trouble with in Boston) they're underpaid in the current marketplace.

The end result of that is that the money Boston saved doesn't have the same value because it won't buy the same talent. OK that's a bit of a hit to take to the organization's overall talent level, so how do you replenish? One way is to do what Cherington has been doing, to hit the free agent market with abandon. But that's not enough. You can't afford to pay everyone at free agent price levels. You also need young talent and that's what the Red Sox got from the Dodgers.

Many of us have spent this off-season pining over Giancarlo Stanton (I've been a driver of that bus). The idea is that the Red Sox need to inject their system with young, high-end talent, and yet maybe, right under our noses, they already have. Webster ranks fourth in the Red Sox system according to Baseball Prospectus and De La Rosa, who has thrown too many major league innings to make the list, is ranked ahead of him on the list of Boston's Top 10 Talents 25 and Younger. Those are impressive young pitchers. That is an impressive haul.

I don't think for a minute the Red Sox made the Punto Trade just to acquire prospects. The money Boston saved in the deal is important and it will be (and has been) spent to improve the team. So, by the way, was the changing of a non-functioning clubhouse culture. But listening to Epstein's interview highlighted the importance of Webster and De La Rosa to the Red Sox system, and the Red Sox future. A quarter billion dollars is a lot of money, but even that won't buy what it used to and it can't buy young elite pitching talent. Maybe that was more of a driver in the Nick Punto Deal than we thought.