Cubs overlord maximus Theo Epstein was of course general manager of the Red Sox when they snapped their World Series drought in 2004 and for their follow-up act in 2007. Retired right-hander and occasional social media firebrand Curt Schilling was a member of each of those championship squadrons, which means he had occasional Business Dealings with Mr. Epstein. 

Speaking of which, Epstein recently appeared on an episode of the “Pardon My Take” podcast and at one point discussed a rather notable contract negotiation with Mr. Schilling. Via SI’s Extra Mustard, here’s the relevant transcript ... 

Epstein: So we were negotiating back and forth. He had fired his agent and he was representing himself. We were negotiating a contract extension back and forth.

PMT: That’s a mismatch. (Laughs)

Epstein: Yeah, that’s what I thought. I thought we were doing pretty well in the negotiations. So we reach a deal. We’re happy with it and we go back to print it out in his little home office. We were using his computer and his printer to print it out and there on his desk is a well-worn dog-eared copy of the book Negotiating for Dummies ... Every time he was pretending to go to the bathroom, he was running back and looking at that book.

Pretending to go to the bathroom? Curt, my man, you gotta write those notes on your hand with a Bic felt-tip pen. Everyone knows that best practices for cheating on an eighth-grade biology quiz also apply to high-level negotiations in the private sector. 

Anyhow, while Schilling got an extension before being dealt to the Sox from Arizona in late 2003 in exchange for waiving his no-trade clause, the guess here is that this particular strategy was employed during talks prior to the 2008 season. Schilling wound up not pitcing in ‘08 after undergoing surgery and then retiring, but he was under contract in Boston for that year. Via Baseball Prospectus, here some details about that final deal ... 

1 year/$8M (2008). Re-signed by Boston as a free agent 11/6/07. $0.5M one-time assignment bonus if traded. Performance bonuses: $0.375M each for 130, 140, 150, 160, 170, 180, 190 & 200 IP. Award bonuses: $50,000 for All Star starter. $0.1M each for All Star, LCS MVP, WS MVP. $0.5M for Cy Young ($0.4M for 2nd, $0.3M for 3rd, $1M for receiving one Cy Young vote (1st, 2nd or 3rd). $2M in weight clauses ($333,333 each for maintaining weight in 6 random weigh-ins, one per month, during season). Perks: use of team uniform for charity events, suite for home-game starts and charity events, day care for home games, 6 season tickets in State Street Pavilion. Retired 3/09.

It’s possible this scribe is wrong, of course, but something about those contract wrinkles bellows, “forged while pretending to use the toilets of America.” 

People, life is not an open-book test, except when it is.