Game Time: The Caballo Chronicles, Volume 2: A Look at MLB's 20 Biggest Contracts Ever

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This is my second go round living in Houston. Prior to moving back here in the summer of 2007, the last time I was an H-town resident was between 1994 and 2001. As an Astro fan, that means I was here when the Bagwell/Biggio nucleus finally broke through in 1997 and made the playoffs, I was here when they added Randy Johnson and bowed out disappointingly to San Diego in 1998, and I was here when they moved into the new ballpark in 2000.

I moved to Denver in 2001, but I never stopped liking the Astros. However, unless it's your team you rooted for growing up (for me, the Boston Red Sox), as an adult when you move away from a city, you generally leave those teams behind, at least in terms of feeling any acute pain when they lose. You still follow them, you still hope they win, but the day to day grind of being a fan in their backyard just isn't there.

I wasn't in Houston in 2004 when Carlos Beltran almost carried the Astros to the World Series, and I wasn't in Houston in 2005 when they kicked the door in and finally made it. I point this out and concede that the pain of being played by Beltran in free agency after 2004, and the gut punch of being one big stick away from winning a world title in 2005 were not acute pain to me like they were to those of you who were here at the time.

To talk to a few people who cover the Astros whose opinions I respect, by the time the offseason after the 2006 season rolled around, fans of the team were tired of the team's offensive ineptitude and embarrassed at how the team always finished second fiddle for big name free agents (and in the case of Beltran, get taken for a ride in the process).

Enter Carlos Lee.

The other question I had for my friends covering the Astros was "How was the Lee signing received by fans when it happened?" It's easy to judge it now, three years in, and talk about in retrospect what a crippling blow it now appears to be, but the fact of the matter is that from strictly an emotional standpoint, you could see where Astro fans would be anywhere from okay with it to genuinely excited about it.

"We finally made a big splash in free agency!" At the time he signed, the total value of Lee's contract was among the biggest dozen or so in big league history. Today, it's still 20th overall, according to Wikipedia. The Lee signing was not the norm for the Astros; in the high-rise apartment building that was MLB salary spending, the Astros had a nice duplex and a good view, but never ventured up to the penthouse. With the Lee signing, they finally decided to see what the fuss on the roof was all about.

In retrospect, until 2006 being an Astro fan during free agency spending was like still being a virgin in your early 20's. I would imagine you reach a point where it doesn't matter so much who you end up having sex with, just that eventually you have sex with someone. Didn't matter for Astro fans that they popped their cherry with a one-dimensional outfielder who was a few biscuits away from being a pulling guard in the NFL, they were now a team willing to spend and play with the big boys.

But that's the problems with decisions made on emotion -- typically, they end up backfiring. And the Carlos Lee signing has started in on a multi-year backfire that will leave the Astros anywhere from moderately hindered to outright crippled the next two-plus years.

Remove the emotion from the transaction and evaluate it strictly as a baseball decision, and it's prudent to ask "Did the Carlos Lee signing make baseball sense at the time it happened?" Remember, this was not a three year deal for a complementary infielder or a middle reliever; this was one of the top fifteen contracts in the history of the game. (Today, as I mentioned earlier, it's still the 20th largest ever signed in terms of total dollars.)

I'm sure sabermetricians have certain statistical thresholds that dictate whether or not you spend ridiculous money on players, and they probably have certain positions that have valuations where it says you just plain never spend crazy money, but my completely unscientific list of qualities that would have to be possessed by a player I would give over $100 million to would look something like this:

(NOTE: This assumes I am running a team that has to exercise some level of fiscal responsibility; if I'm running the Yankees, the list of qualities to give $100 million to someone looks like this: (1) made an All-Star team in last two years; (2) has pulse.)


  1. No older than 30 at time of signing
  2. Must be younger than 35 when the contract would expire
  3. Career best season must be within last two seasons
  4. If a player is coming off their career best season, they must have had a similar season the year before (vital stats like home runs, OPS within 10%); if they did not, then they must have at least two seasons in last four within 10% of their best year (DON'T pay one year wonders!)
  5. Must be a plus defensive player (upper half in range factor, plus arm from outfield, eyeball test)
  6. Slight bending of these rules for hometown players (i.e. Joe Mauer in Minnesota, Ken Griffey in Cincinnati) or signing products of your own farm system (i.e. Todd Helton in Colorado). This is the ONLY emotion I would allow in the assessment, because with players of this caliber, public relations/"face of the franchise" value matters.

For pitchers the rules are generally the same (different vital stats, and probably bigger cushion than 10%), but understand that the market for pitching will be crazier than any position player as far as valuation goes, marquee teams with fewer fiscal restrictions driving prices up (see Sabathia, Burnett in 2009; Lackey in 2010), And teams are more willing to pay for smaller bodies of work; in short, you're best served to grow pitchers from the farm up.

With those general, largely non-statistical rules in mind, let's assess the Top 20 contracts in baseball history and see how defensible they were at the time of signing, and how defensible they are today. Carlos Lee, conveniently (and nauseatingly) enough, has a contract worth exactly $100 million in total and is 20th on the list, so this is essentially an exercise to see if Carlos Lee is the single most indefensible $100 million-plus contract in baseball history.

Here we go....

We'll create a subjective Defensibility Rating system that goes as follows:

1 - Completely Indefensible - franchise killer 2 - Somewhat Defensible - sketchy, risky, but explainable (likely to be invoked often on starting pitchers) 3 - Very Defensible - aligns with most of the Pendergast tenets of giving out $100 million 4 - Totally Defensible - airtight case, no brainer

1. Alex Rodriguez, NYY 10 years, $275M (2008-2017)

REASONS FOR YANKEES TO EXTEND HIM IN 2008: This contract was actually a de facto contract extension that A-Rod got from the Yankees after opting out of his $252 million deal that he originally signed with the Rangers. (Perhaps you remember his doing this right in the middle of the World Series that year.) He was coming off a year where he went .314-.422-.645 and hit 54 home runs, and a five year period where he was named MVP three times. He was 31 years old at signing, which puts the Yankees on the hook until he's 39, but it's the Yankees. They can afford it.

REASONS FOR YANKEES TO STAY AWAY IN 2008: Hard to say "steroids" in this exercise because A-Rod hadn't yet been exposed and was not a regular on the suspicion short list back in 2007. Post-season fades were an issue then (That's been rectified now.), but the regular seasons were just too good.


2. Alex Rodriguez, TEX 10 years, $252M (2001-2010)

REASONS FOR RANGERS TO SIGN HIM IN 2001: Coming off three straight 40+ home run seasons and an average OPS over the previous three years of somewhere in the mid .900's, numbers that are ungodly for any position, let alone shortstop, there really wasn't much to dislike. Especially considering that Rodriguez was 24 years old at the time.

REASONS FOR RANGERS TO STAY AWAY IN 2001: Even fewer reasons back then to stay away than there were when he did his extension in 2008 -- like no real reasons. The only thing you needed to guard against was bidding against yourself. So naturally the Rangers committed to about $100 million more than the next highest bidder.

CONTRACT DEFENSIBILITY RATING (at signing): 3 -- Rangers inability to spend on anything else after signing A-Rod keep this from being a 4 CONTRACT DEFENSIBILITY RATING (today): 2 -- They ended up flipping A-Rod for Alfonso Soriano and then flipping Soriano for prospects and had to pay off a massive chunk of A-Rod's deal anyway. The fact that Rodriguez actually produced keeps this from being a 1.

3. Derek Jeter, NYY 10 years, $189M (2001-2010)

REASONS FOR YANKEES TO EXTEND HIM IN 2001: At age 26, he was the face of a franchise that had won four World Series in five years, and from 1998-2000 he sported a .337 batting average and a .918 OPS from the shortstop position.

REASONS FOR YANKEES TO STAY AWAY IN 2001: None. Best player/team fit for each other of this era.


4. Joe Mauer, MIN 8 years, $184M (2011-2018)

REASONS FOR TWINS TO EXTEND HIM IN 2010: The Jeter equivalent for the Twins, but for different reasons. He's the hometown kid made good and the centerpiece of this era of Twins as they head into their new ball park. Oh, that and at age 26 he had three batting titles, two Gold Gloves, and an MVP award. And a partridge in a pear tree.

REASONS FOR TWINS TO STAY AWAY IN 2010: If you're the Twins, you have to be careful not to invest too much in one player, but with a new ball park and Mauer's crazy ceiling as a player it's a chance worth taking. Put it this way -- if you're the Twins, if not Mauer then who? No one.


5. Mark Teixeira, NYY 8 years, $180M (2009-2016)

REASONS FOR YANKEES TO SIGN HIM IN 2009: About as safe and consistent a power hitter as you'll find. From 2004-2008, averaged 152 games per season (durable), 35 home runs (hits for power), a .295 batting average (hits for average), and an OPS of .938 (all around offensive game). He also won a couple Gold Gloves (he can field!). Yeah...lots of reasons.

REASONS FOR YANKEES TO STAY AWAY IN 2009: With most other teams, there might have been risk paying him that much money into his late 30's, but the Yankees...well, they paid Jason Giambi almost $20 million per year to be a below average power hitter after he got off the juice and barely felt the sting. So, risk shmisk.


6. C.C. Sabathia, NYY 7 years, $161M (2009-2015)

REASONS FOR YANKEES TO SIGN HIM IN 2009: Productive workhorse who had done his best work in games that mattered down the stretch in 2008 when the Brewers went out and made the midseason deal to bring him in. Averaged 2.95 ERA in 2007 and 2008, over 240 innings pitched per year those two seasons, and in his career had made fewer than 30 starts in only one season (28 in 2006). A beast entering his prime.

REASONS FOR YANKEES TO STAY AWAY IN 2009: The workload in 2008 included lots of "three days rest" starts down the stretch, so tread on the tire was a minor issue. Plus, conditioning has never been high on Sabathia's priority list.

CONTRACT DEFENSIBILITY RATING (at signing): 3 - $161 million for a pitcher that massive (ok, FAT) is a risk, even for the Yankees CONTRACT DEFENSIBILITY RATING (today): 3.5 - one more title with Sabathia as a core piece and it's a 4, regardless of what happens the next five years under the "Two World Titles trumps Five Injury Filled Years Corollary"

7. Manny Ramirez, BOS 8 years, $160M (2001-2008)

REASONS FOR RED SOX TO SIGN HIM IN 2001: From 1998-2000, Manny the Hitting Savant was in "Raymond Babbitt in Vegas" mode, averaging 42 home runs, 144 RBI, and a BA-OBP-Slugging line of .324-.423-.649. He was three years into what would become an eight year run of top 10 MVP finishes.

REASONS FOR RED SOX TO STAY AWAY IN 2001: If MLB offered a Wonderlic test to its players like the NFL does for draft prospects, Manny might be the first player to score a negative grade. Plus, his postseason performances to that point had been a tad underwhelming.

CONTRACT DEFENSIBILITY RATING (at signing): 4 - Who cares about the baggage; dude could mash CONTRACT DEFENSIBILITY RATING (today): 4 - Two world titles, one World Series MVP, enough said

8. Miguel Cabrera, DET 8 years, $152.3M (2008-2015)

REASONS FOR TIGERS TO EXTEND HIM IN 2008: Averaged .318-32-115 in his first four full seasons with an OPS of .947. In that time frame, his low OPS was .879 and his high was .998 (in 2006). His RBI total had a window of 112 as a low and 119 as a high. In other words, he was the model of consistency. Oh and he was 24 years old! And in his one partial season in 2003 (rookie year), he was a key member of a world champion.

REASONS FOR TIGERS TO STAY AWAY IN 2008: Two of the top 5 hitters that baseball-reference.com lists as similar to Cabrera are Kevin Mitchell (1) and Bob Horner (5). Both were portly corner infielders. So was Cabrera. Just saying.

CONTRACT DEFENSIBILITY RATING (at signing): 4 CONTRACT DEFENSIBILITY RATING (today): 3 - a bit more cautious after a few discipline issues with booze. Let's be clear, Miguel -- drunk playing softball...good. Drunk playing major league baseball...bad.

9. Todd Helton, COL 11 years, $141.5M (2001-2011)

REASONS FOR ROCKIES TO EXTEND HIM IN 2001: Even for the video game numbers spit out by Coors Field in the late 1990's, Helton's numbers were crazy, capped by a 2000 season where he led the league in hits, doubles, RBI, batting average, on base percentage, and slugging. One of the truly great offensive seasons ever. Also considered an excellent glove man and a leader in the clubhouse. Perfect face of the franchise in Denver.

REASONS FOR ROCKIES TO STAY AWAY IN 2001: Eleven years is a long time in any sport, job, or walk of life. If it were any other team signing Helton, you'd cite concern over inflated stats in Coors Field, but for the Rockies that didn't really matter.

CONTRACT DEFENSIBILITY RATING (at signing): 4 CONTRACT DEFENSIBILITY RATING (today): 3 - Helton has gone from offensive uber-god to, by the middle of the decade, a solid offensive first baseman (still had .905 OPS from 2005-2009); think a more potent version of Will Clark.

10. Johan Santana, NYM 6 years, $137.5M (2008-2013)

REASONS FOR METS TO EXTEND HIM IN 2008: Quite simply, by age 28, Santana was the best pitcher in baseball with a 2.92 ERA and a WHIP barely above 1.00 for the period of 2003 through 2007. He also won two Cy Youngs and finished in the top seven three other times.

REASONS FOR METS TO STAY AWAY IN 2008: In 2007, his numbers were slightly worse, but nothing too scary -- still good enough for fifth in the Cy Young balloting (I'm grasping for straws).


11. Alfonso Soriano, CHI 8 years, $136M (2007-2014)

REASONS FOR CUBS TO SIGN HIM IN 2007: In 2006, became just the fourth player in history to hit 40 home runs and steal 40 bases in the same season. This mix of power and speed was other worldly when he was a second baseman earlier in the decade, and still pretty damn good as an outfielder. Also, his time in New York showed him what the hottest spotlight feels like so the big stage doesn't scare him.

REASONS FOR CUBS TO STAY AWAY IN 2007: A sabermetrician's nightmare, Soriano has had a handful of seasons where he he's garnered more home runs than walks. Also, there's a reason they kept moving him around defensively, and it's not because of how awesome he is. Also, turned 31 in 2007, so you're likely paying him into his late 30's (assuming his age is even accurate).

CONTRACT DEFENSIBILITY RATING (at signing): 2 - paying him over half the deal after he turns 35 is an issue; Cubs solid financial wherewithal keeps it from being a 1 CONTRACT DEFENSIBILITY RATING (today): 1 - add frequent injuries (average 120 games per season 2007-09) to defense in left field that makes Manny Ramirez look like Torii Hunter. Yeah, not good.

12. Vernon Wells, TOR 7 years, $126M (2007-2013)

REASONS FOR THE BLUE JAYS TO EXTEND HIM IN 2007: Lots of reasons to extend him (just not many to sign him for $18 million per year). Gold Glove outfielder, but inconsistent, undisciplined hitter with an OPS of .853. Still, made a couple All-Star teams between 2003 and 2006, and at age 27 managed a .303-32-106 season. It was trending up for him, I'll say that.

REASONS FOR BLUE JAYS TO STAY AWAY IN 2007: Remember the scene in Risky Business when the guy from Princeton admissions comes to Joel's house to interview him as a prospective student, and he goes through his vital stats (SAT, GPA, extracurriculars). His assessment: "You've done some solid work here, Joel; but it's just not quite Ivy League now, is it?" Well, Vernon Wells is Joel. Solid work, but not quite $18 million per year solid now, is it Vernon?

CONTRACT DEFENSIBILITY RATING (at signing): 2 CONTRACT DEFENSIBILITY RATING (today): 1 - If it were the Yankees, maybe it becomes a 2, but the Blue Jays had to dump the best pitcher in the league (Roy Halladay) this off season, so paying an average outfielder eight figures is probably not a wise decision.

13. Barry Zito, SF 7 years, $126M (2007-2013)

REASONS FOR THE GIANTS TO SIGN HIM IN 2007: Quintessential workhorse, averaging 225 innings pitched per year from 2002 through 2006 with an ERA of 3.63 (which you'd expect to go down closer to 3.00 in the National League). Not a hard thrower so risk of injury is theoretically lower.

REASONS FOR THE GIANTS TO STAY AWAY IN 2007: Not always perceived as someone who lives and dies with baseball, which...I don't know...might be part of the criteria if I were about to pay someone $18 million per year. Also, other than Cy Young season in 2002 (23-5, 2.75 ERA) had never really had a truly dominant season. Biggest red flag: he was four years removed from his best season in Oakland (his only season wirth $18 million in 2007 terms) when San Francisco signed him.

CONTRACT DEFENSIBILITY RATING (at signing): 3 - If it were anything but a workhorse starting lefty, it'd be a 2 without question. CONTRACT DEFENSIBILITY RATING (today): 1 - I want so badly to give this signing something better than a 1 because I think Zito can still pitch, but all evidence is to the contrary since he arrived in San Fran, with ERA's over 5.00 being the norm. Third best pitcher in his own rotation behind Lincecum and Cain.

14. Mike Hampton, COL 8 years, $121M (2001-2008)

REASONS FOR THE ROCKIES TO SIGN HIM IN 2001: Honestly, look at Hampton's per season numbers from 1997 through 2000 and their almost identical to Zito's from 2002-2006 -- averaging 16 wins, 3.30 ERA, 223 innings pitched. Also, a bunch of solid years and one dominant year in 1999 (22-4, 2.90, 2nd in Cy Young). The differences between Hampton pre-2001 and Zito pre-2007 are (1) Hampton was only one year removed from his best season, and (2) he comes across as more competitive than the mild mannered Zito.

REASONS FOR THE ROCKIES TO STAY AWAY IN 2001: Only one truly dominant season where he was the hammer every time he went out. Other than that, what wasn't to like about a 27 year old lefty that you could pencil in for 30+ starts, an ERA around 3.00, and a red ass every time out?

CONTRACT DEFENSIBILITY RATING (at signing): 2 - Colorado had to overpay to get pitching because in their first eight years in the league, their best pitcher was Pedro Astacio. Trust me, I lived in Denver when this signing went down, they were desperate. CONTRACT DEFENSIBILITY RATING (today): 1 - It looked like it might work out, with Hampton making the All-Star team in his first season (2001), but it all unraveled shortly thereafter and what started out as a semi-major, but necessary risk for the Rockies turned into a disaster that completely changed the way the Rockies evaluated talent and structured their team. The poster contract for excess shocking a mid-market team into embracing moneyball philosophies.

15. Jason Giambi, NYY 7 years, $120M (2002-2008)

REASONS FOR THE YANKEES TO SIGN HIM IN 2002: From 1998 through 2001, averaged 35 home runs and a 1.024 OPS while winning one MVP award (2000) and finishing runner-up for another (2001). Actually, other than being a year or two older and not as good a glove man, Giambi in 2001 was Teixeira before Teixeira came along. Of course, now we know why. (Juice....cough....juice....)

REASONS FOR THE YANKEES TO STAY AWAY IN 2002: Age, Giambi turned 31 the winter before he started in on the seven year deal from the Yankees, and sure enough durability became a major issue later in his Yankee career. Of course, without steroids you don't heal quite as fast either.

CONTRACT DEFENSIBILITY RATING (at signing): 4 CONTRACT DEFENSIBILITY RATING (today): 1 - Somehow it feels like the karma gods got this one right -- the Yankees won zero titles while Giambi was there. (Of course, that doesn't explain winning one with A-Rod. Damn you, karma gods!)

16. Carlos Beltran, NYM 7 years, $119M (2005-2011)

REASONS FOR THE METS TO SIGN HIM IN 2005: At age 27, the arrow was pointing up in every way. Five tool player whose OPS in two year chunks went from .749 in 1999-2000 to .861 in 2001-2002 to .913 in 2003-2004. Two home runs away from becoming, at the time, the fourth 40-40 player in baseball history. Also, in his first post-season in 2004, had an OPS of over 1.500, which is frankly ridiculous.

REASONS FOR THE METS TO STAY AWAY IN 2005: Offensively, his best seasons were really good, but other than almost getting to 40-40, nothing otherworldly. But I'm totally nitpicking now.

CONTRACT DEFENSIBILITY RATING (at signing): 4 CONTRACT DEFENSIBILITY RATING (today): 3 - Maybe I wasn't nitpicking because Beltran has been really good, but is missing that little something that separates really good from special.

17. Ken Griffey, Jr. CIN 9 years, $116.5M (2000-2008)

REASONS FOR THE REDS TO EXTEND HIM IN 2000: Because he's now been around for so long and is so far removed from being an elite player, we forget how truly great young Griffey was. Before he could legally drink, he had already won a Gold Glove and garnered MVP consideration. This may be another post for another time, but you'd be hard pressed to find anyone who had a Hall of Fame resume already accumulated before the age of 30 (A-Rod probably, but the steroids hurt his chances, at least for now). I don't mean that at 30 you know he's GOING to be a Hall of Famer, I mean at age 30 Griffey could have retired and he'd have been a Hall of Famer. He was the best center fielder defensively in the game (Gold Glove every year from 1990-1999) and by the time his first stint in Seattle had ended in 1999 he had nearly 400 home runs and an OPS of .948 to go along with one MVP award and four other top five finishes. In the four year period of 1996-1999 he averaged 52 home runs and 142 RBI. Above all else, he (along with A-Rod and Randy Johnson) completely changed the losing culture of one of the worst franchises in team sports. Also, one last thing -- he grew up in Cincinnati, so add that to the reasons this may have been the biggest no brainer ever at the time.

REASONS FOR THE REDS TO STAY AWAY IN 2000: He was turning 30, so this contract was going to take him to 38 (power hitting outfielders generally start to tail off by their mid-30's), and Cincinnati, as a smaller market, doesn't have the margin for error if it doesn't work out.

CONTRACT DEFENSIBILITY RATING (at signing): 4 - Easily CONTRACT DEFENSIBILITY RATING (today): 1 - It certainly didn't work out the way anyone drew it up. I mean, did anything else look more perfect on paper than Griffey coming home to Cincy?

18. Kevin Brown, LAD 7 years, $105M (1999-2005)

REASONS FOR THE DODGERS TO SIGN HIM IN 1999: He was one of the top five pitchers in baseball from 1996 through 1998 with a 2.33 ERA to go with a manly 242 innings pitched per season and WHIP and K/BB among the best in the league. Also, pitched in two postseasons winning a World Series with the Marlins in 1997 and getting there with the Padres in 1998. (Note: Didn't pitch real well in either World Series, worth noting.)

REASONS FOR THE DODGERS TO STAY AWAY IN 1999: Two things -- one, he was going to enter the 1999 season at age 34, so a seven year deal was going to take him into his early 40's; two, Brown was a bit of a surly dude who had his ups and downs between the ears during his career.

CONTRACT DEFENSIBILITY RATING (at signing): 2 - Productivity + advanced age + head case = risky but hopeful signing; if it were a position player getting signed to this deal at age 34, it would be a 1 CONTRACT DEFENSIBILITY RATING (today): 1.5 - In the end, the good was good and the bad was pretty bad, and there was more bad than good. Only two Cy Young candidate years in 1999 and 2000 save this from being a 1.

19. Albert Pujols, STL 7 years, $100M (2004-2010)

REASONS FOR THE CARDS TO EXTEND HIM IN 2004: Because even after just three years, at age 23 you could tell this is going to be a once in a generation type hitter. And he's been just that. I could spit out OPS and home run stats all day long. I'll just leave it at this -- Pujols has been in the league nine full seasons, and in MVP balloting his finishes in order (2001-2009) look like this: 4,2,2,3,1,2,9,1,1. Whoa.


CONTRACT DEFENSIBILITY RATING (at signing): 4 CONTRACT DEFENSIBILITY RATING (today): 5 - In honor of Pujols' jersey number, I give him the only higher than maximum score of any of the players named in this post for being the biggest big-dollar bargain in team sports.

20. Carlos Lee, HOU 6 years, $100M (2007-2012)

REASONS FOR THE ASTROS TO SIGN HIM IN 2007: Remember we're removing the emotion of franchise history from the equation (so previous free agent jiltings and teases don't factor in). We're evaluating this on (1) Carlos Lee as a player and (2) his salary as a function of the Astros ability to afford it, especially if he doesn't work out. So with that said, the positive -- Lee was a run producer (110 RBI per year from 2003-2006) and the Astros needed a run producer. That's it. That's the only reason to sign him.

REASONS FOR THE ASTROS TO STAY AWAY IN 2007: Where to begin -- let's start with age. Carlos Lee turned 31 in his FIRST season of this six year deal. Hitters with Lee's profile (and waistline) generally start to decline around 33. Today, at 33 years of age, Carlos Lee is hitting .104 twelve games into the season and coming off a year where he hit only 26 home runs in 160 games. Next, from 2004 through 2006, Lee played for three different teams. This, to me, is a red flag for anyone that you're going to pay transcendent superstar money to. Sorry, if he were that good, $100 million good, one of the three teams he was on during the previous three seasons would have kept him. They'd have found a way. Finally, Lee is a one dimensional player who can barely field his position. Unless your name is "Manny Ramirez," you have no business being a butcher in the outfield and making $100 million. You just don't. Finally, there was no hometown "face of the franchise" value in this signing either like there was with Lance Berkman (Rice grad) and Bagwell/Biggio (grew up with the franchise from virtually the beginning of their careers).


...and boom goes the dynamite.


So looking at the top twenty contracts in the history of the game, the thing that jumps out at me is the line drawn right in the middle of the list. Of the top ten contracts in the history of baseball, by my purely subjective assessment, only A-Rod's first contract and the Sabathia deal rank below a perfect 4 on the Defensibility Scale at the time of signing, and that's only because in both cases the teams inking the deals were bidding against themselves (and Sabathia's weighing 300+ pounds factored in also). Even more amazing than that is that the deals have largely worked out for the teams involved, with the only one getting below a 3 being the first A-Rod deal and that's only because the Rangers couldn't afford him. A-Rod was actually ultra-productive, winning an MVP in his final year in Texas.

The second ten turns into a depressing circus of managerial ineptitude and desperation. Of those ten players, all but Carlos Beltran and Albert Pujols could be classified as out and out failures and/or franchise crippling contracts. So I guess the good news is there are fans in San Francisco, Denver, Los Angeles, and Toronto that feel your pain, Astro Fan. Thankfully, with Facebook and Twitter, they've never been more easy to connect with, and therapy has never been more accessible. It appears we'll need it for at least three more years.

Listen to Sean Pendergast on 1560 The Game from 3-7 PM weekdays on the "Sean & John Show", and follow him on Twitter at http://twitter.com/SeanCablinasian.

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