When a team signs a player to a nine-figure deal these days, it usually isn’t looking for the big payoff to come at the end. The end is a necessary burden—the consequence of locking in what might be a few more years of stardom in a sport where fewer and fewer stars ever hit free agency and there aren’t five—win players around every corner.

For the Giants and Barry Zito, though, there is some weight put on the end of the deal. With no rotation depth, the Giants are counting on Zito to show that even with his 2012 postseason performance exceeding his true talent, his 16 innings, three runs allowed, six walks and 13 strikeouts were at least a sign that there’s something there.

Besides, Zito’s end is all he has left after compiling a grand total of 1.8 wins above replacement player over the first six years of the $126 million contract.

The end tends to be ugly, though it hasn’t always been for baseball’s $100 million men. Some do just fine in their last guaranteed years, even at times parlaying them big paydays. Others flop and are never seen again.

Where Zito ranks on this list of best and worst final guaranteed seasons of $100 million deals will have a big impact on the Giants’ chances in 2013.

1. Albert Pujols 2010 (age 30)
9.0 WARP for the Cardinals
$16M of 7-year/$100M deal

No wonder this was considered the best contract in the game for much of the 2000s. The 2010 season was just the final guaranteed season, and one that would have gotten the Cardinals out of a relatively light $100M obligation with 65.4 WARP—which could be a Hall of Famer’s whole career. The fascinating part about the tail end of this one is that it resembles where we are now in the first Justin Verlander extension (5/80M through 2014). It’s a great player with no visible signs of slowing down hitting his final guaranteed year at age 30—Verlander will be 31 when his deal with the Tigers would have ended. Instead of going long-term extension, though, the Cardinals just exercised the gimme option for 2011 and then let somebody else preside over the decline.

2. Manny Ramirez 2008 (age 36)
6.9 WARP, 2.7 for the Red Sox and 4.2 for the Dodgers
$20M of 8-year/$160M deal, plus $1M trade bonus

Nowhere is memory—at least the author’s—more disconnected from reality than the end of this deal, which feels like a total disaster but is the second-best ending to a nine-figure contract that we’ve seen. His 53 games in Los Angeles alone (.396/.489/.743) were enough to net him fourth in the MVP voting, and he was a voting point away from third and more valuable to his NL team that year than Ryan Howard, who finished second. While Boston despised his act, he was playing at not just a high level but an all-star level (lowercase) when he left. When Boston signed Ramirez, he was coming off his best year by rate stats and the Red Sox smartly didn’t let a hamstring injury get in their way. This deal was good until the last fight with a traveling secretary.

3. Alex Rodriguez 2010 (age 34)
4.8 WARP for the Yankees
Originally $27M of 10-year/$252M deal with Texas, changed to $32M after opt-out.

What a time this would have been for the Yankees to say goodbye, as this would have been the final year of the contract they acquired for Alfonso Soriano and Joaquin Arias. But Rodriguez wisely opted out in 2007, prompting the Yankees to say goodbye not a little too early, but way too late. Looking at the original deal, though, it appears very, very reasonable even as the largest deal ever given out to that point. Few players are able to go 10 years in and still be 34—Bryce Harper won’t even be able to do that unless it’s a in deal with the Nationals or their trade partner that starts before free agency would naturally kick in.

4. Carlos Beltran (age 34)
3.8 WARP, 2.5 for the Mets and 1.3 for the Giants
$18.5M of 7-year/$119M deal

How good was Beltran even as this contract was reaching its end, even around nagging leg problems and a wrist injury that shortened that final season? Well, Zack Wheeler, the man traded for Beltran in the middle of that final season, is the no. 5 prospect in all of baseball on Jason Parks’ list. Okay, so that was a bit of an overpay, but Beltran survived all the injuries remarkably well and turned the final year of his big deal into a very nice two-year deal afterward. While there were years when it looked like the Mets would suffer the winners’ curse after the fierce race to sign Beltran away from the Astros, that final season and the acquisition of Wheeler changed the equation significantly.

5. Todd Helton 2011 (age 37)
2.8 WARP for the Rockies
Originally $19.1M of 9-year/$141.5M deal, changed to $6M after restructuring extension with large deferrals.

This was the classic win-now, pay-for-it-later contract, although what was supposed to be the last year didn’t show it. The Rockies got two MVP-caliber years out of Helton, which happened to be the first two, and two other very good seasons (in years three and five). The rest of it was just an aging first baseman with a declining skill set and the ballpark adjustment. That 2011 season was Helton’s median production year, but it’s since been followed in the restructured deal by his only two below-replacement-level seasons.

6. Jason Giambi 2008 (age 37)
2.1 WARP for the Yankees
$21M of 7-year/$120M deal

One of the most directionless and wildly changing contracts on the list probably ended appropriately with a mediocre season in the year that broke the Yankees’ 13-season playoff streak. Giambi could still walk by the end (in the baseball sense, rather than the true ambulatory sense) and could still drive it out in the final year in the new Yankee Stadium, but he didn’t hit frequently enough to make subpar defense at an easy position all that worthwhile. The Yankees didn’t get ripped off here, but it was an easy call to decline a $22 million club option and eat a $5 million buyout in an immediate transition to the Mark Teixeira era, which threatens to end similarly in 2016, though surely with better defense.

7. Kevin Brown 2005 (age 40)
1.2 WARP for the Yankees
$15M of 7-year/$105M deal

If Kevin Brown’s whole legacy is being underappreciated, we’ll try to reverse that in this list, which probably overappreciates him with a WARP value based heavily on the peripherals. He walked only 19 and struck out 50 in his final 73 1/3 innings amid constant back problems that resulted in career-ending surgery. But thanks in part to a .385 BABIP, he did compile a 6.50 ERA that left a permanent stain on his career that is remembered harshly for the way it ended in a bad city in which to fail.

T8. Ken Griffey Jr., 2008 (age 38)
0.6 WARP, 0.6 for the Reds and 0.0 for the White Sox
$12.5M of heavily deferred 9-year/$116.5M deal

It wasn’t shocking that the end of this contract proved to be bad, because everything but the great first year in Cincinnati proved to be bad. He was hurt, he’d completely lost the speed element of his game, and he was a fraction of himself when he mercifully waived his 10-and-5 rights to go to the White Sox halfway through his eighth and final season with the Reds. The epilogue in Seattle wouldn’t go much better for the king of the 90s.

T8. Derek Jeter 2010 (age 36)
0.6 WARP for the Yankees
$21M of 10-year/$189M deal

Sure, his fielding was below average, as it’s been according to our Fielding Runs Above Average metric in all 18 years of his career, but this was the first year that offense really killed his value. Combine a .710 OPS with the adjustment you have to make in the new Yankee Stadium, then in its second year, and he added virtually nothing. He compiled 34.6 WARP over the length of the contract, which is less than you’d want, but he probably sold a few jerseys along the way and bounced back a little bit on the three-year, $45 million deal that followed.

10. Mike Hampton 2008 (age 35)
0.3 WARP for the Braves
$15M of original 8-year/$121M deal with the Rockies

With no outstanding years, the Rockies were (over)paying for consistency and durability, and that’s hardly what the Braves were getting by the end. The end of this deal was a total debacle, though Colorado actually made out okay when the Rockies passed off the worst of it on Atlanta. Hampton was injured all of 2006 and 2007 and became a cautionary example invoked whenever large pitching contracts are handed out.

11. Johan Santana 2013 (age 34)
0.0 WARP for the Mets (will not play)
$25.5M of 6-year/$137.5M deal

Even not playing at all is better than some alternatives with a sunk cost…

12. Carlos Lee 2012 (age 36)
-0.4 WARP, -0.7 for the Astros and 0.3 for the Marlins
$18.5M of 6-year/$100M deal

A contract that looked shaky and foretold a poor ending even through the “good” first half of it and seemed to be somewhat redeemed after a bounceback 2011 proved its doubters not nearly pessimistic enough at the end. A two-tool player became a one-tool player, and the ability to make contact absent any power (nine home runs all year) or secondary skills meant a readily available Quad-A talent would have been an improvement. But the Astros never could bench the big guy, and they ended up eating the salary in a trade to the Marlins that netted them starting third baseman Matt Dominguez. Lee always spoke as if 2012 might be the end, and while nothing has been formalized, he could join Brown as the only ones to hang it up directly after their $100M deals.

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I'd love to see a BP take along these lines about how the new CBA is affecting free agency. With this latest rash of eight and nine figure extensions for players south of 30 years old, the prospect of acquiring impact talent in free agency seems to dim by the day. Is the new CBA to blame? Are GMs getting smarter? Is this just a fad? I'd be curious to see if serious analysis reveals a correlation.