The potential Santana deal-&-sign (wherever he winds up) and the rumored years/dollars involved got me thinking about how these long-term turn out with pitchers.
L-T deals for pitchers shirley didn't get off to a good start when Wayne Garland signed for 10 years w/the Indians (and was released halfway through) during the first wave of free-agency at the then unheard of sum of $2 million (total) IIRC.
Trying to stay a little more recent than that one, the ones below are the 5-year or longer deals that happened to jump to my head first. Feel free to add more if you find them. Each of these also paid the FA at (or close to) the top $$ level at the time. There doesn't seem to be any pattern as to predicting which ones would bomb and which would succeed.
Randy Johnson: 1999 with Arizona (5 years I believe) 35 y/o in year 1 of the deal - How it worked out for the team ... Great! 4 consectutive CY awards leading to the deal being extended before it ran out. (That he then foreced a trade to NY which he parlayed into another extension that didn't work out so well and then forced a trade back which he parlayed into another extension which isn't working out so well shouldn't sully the original signing)
Darren Dreifort: 2001-2005 w/Dodgers .. 29 y/o in 1st year - One of the worst signings EVER! Approx $57mil for a total of 26 starts and 9 wins
Mike Hampton: 2001 w/Colorado for 7 years .. 28 y/o - Only Dreifort keeps this from being worst EVAH! More or less .500 pitcher over 6/7ths of the deal with two different teams and numerous trips to the DL including at least one entire lost season.
Mike Mussina: 2001-2006 w/NYY .. 31 y/o - Winning pitcher in each season, 30+ starts in 5 (27 in the other), and a better than lg avg ERA in 4 of them MFY fans like to disparage this one, fingering Mussina's failure to go undefeated in October as one of the reasons they never won a WS over his time -- but a sober look at this deal shows it worked out reasonably well for both sides.
Pedro Martinez: I believe this one was for 5 years, signed when he was 28 (two years after being traded to Boston) - 4 terrific years plus one injury-shortened one
Kevin Brown: 7 years at age 34 - The three complete seasons (30+ starts) he managed of the seven were all good to very good ... but the other four (two in LA, two in NY) were injury-shortened mediocrities or worse Barry Zito: 7 years at age 29 - Not off to a very good start is it?
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