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Deal or No Deal? Three Keys to Makin’ Deadline Moves

With another MLB trade deadline upon us and most fantasy deadlines looming soon thereafter, it’s time to start dealing. Now is it always imperative to make a move just because some predetermined date in time says you must? No, I’ve never been a proponent of dealing for the sake of dealing.


Unless your team has been leading the pack from the word go (in which case it’d be wise to stick with what you’ve got) or been feeding on the sewage of the basement since April (in which case it’d be wise to bounce that overdue check to the commish), chances are you need to make a trade.

Of course, sometimes making a move can be detrimental. I swung a deadline swap with a buddy last year, sending him Gary Sheffield (at the time a Top-5 fantasy player) for Roy Oswalt and Placido Polanco. Oswalt went 6-2 with a 2.57 ERA in the second half while Polanco batted .348. Sheffield hit .203 before going on the shelf.

(Yes, the trade was only detrimental to him, and yes, our friendship was temporarily bludgeoned.)

Truthfully, I got lucky considering before that move I had an ultimately nixed proposition on the table with another friend that would’ve netted me Eric Gagne (you know, the Texas closer who saved 12 games with a 1.32 ERA before the All-Star break, remember him?). I can’t recall off the top of my head what I was going to be giving up for him, but I do know that it was more than Richie Sexson and a bag of baseballs.

Needless to say, hindsight gave way to elation when Gagne pitched his way into the recesses of the Boston bullpen and onto the waiver wire, sparing me the regret of having been party to the worst fantasy deal of all-time.

So you see? That’s the glory of swinging deals at the deadline, that element of the unknown. Because of that, there remains no fool proof method to deadline maneuvering. Though there are a few keys.

Without further ado…

Key No. 1 — Be thorough with assessments This is the most basic, yet most integral aspect of crafting the successful deadline deal. With two-thirds of the season on the back burner, the only direction you should be looking is forward. However, within this context more often than not that requires looking back to previous years. For various reasons, certain guys simply live for the twilight. You must seek them out, for these are the players who will bring home the most bread in the shortest period of time. Some don’t heat up until the pressure starts to mount (Bobby Abreu, Robinson Cano, David Ortiz) while others just don’t seem to find their stroke until they’re waist deep in the dog days of summer (Garrett Atkins, Mark Teixeira, Nick Markakis) So before locking in a proposal be sure to, you know, cover your bases. (Sorry, I couldn’t resist.)

Key No. 2 — Don’t be afraid to shake things up (aka the Theo Epstein Corollary) A mere four trade deadlines ago, Theo Epstein literally put his career on the line by trading away the iconic Nomar Garciaparra for Orlando Cabrera and Doug Mientkiewicz. The Red Sox were an underperforming .500 ballclub in need of an overhaul. So Theo pulled the trigger on one of the most controversial trades in Red Sox history, a deal that marked a watershed moment for a tortured franchise. My point being, if Theo was willing to assume the burden of seven generations of rabid and crazy Red Sox fans, don’t balk at the prospect of pulling something of a fantasy equivalent. If your team has been sitting middle of the pack, the time has come to part with a titan. Max out the value of a Josh Hamilton, Adrian Gonzalez, Carlos Quentin or Nate McLouth by packaging one of them and going in a different direction. It’s worked before. (And as opposed to Theo, if it all fails you won’t have to board up your windows.)

Key No. 3 — There’s no harm in asking (aka the Danny Ainge Corollary) When Ainge (the Celtics GM) sent to his buddy Kevin McHale (the Timberwolves GM) a pu pu platter wrapped in a green ribbon, not many believed Kevin Garnett would emerge in return. True, most fantasy commissioners would scream collusion if something similar happened between friends in fantasy baseball, but hey, if Ainge and McHale were able to pull one over David Stern, I say anything is possible. So for all you owners out there still stewing over the 11th pick you received in the draft, make your play for Hanley or Utley. Worst case scenario is a rejection. (Or put another way: A supermodel isn’t going to ask you out. You just gotta try your luck.)

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