The Best Extensions From Two Offseasons Ago

Back in January, MLBTR's Tim Dierkes looked at the extensions from the 2009-10 offseason that are already looking like (or have proven to be) mistakes.  While some teams rue those deals, other teams have benefited.  While the jury is still out on a few of the longer-term contracts (i.e. Roy Halladay, Denard Span, Justin Upton), a few extensions signed between October 1, 2009 and April 5, 2010 are already clear wins for teams.

• Matt Cain.  Before Cain signed his six-year, $127.5MM extension with the Giants last April, there was talk that the MLBPA was watching the negotiations with interest due to the perception that Cain had already signed two team-friendly extensions in his career.  It's hard to argue that San Francisco got a deal on Cain's three-year, $27.25MM extension from March 2010.  Cain was already owed $4.25MM for 2010 and (on a team option) $6.25MM for 2011, and his new deal gave those numbers a minor bump up to a guaranteed $11.25MM for 2010-11, plus $15MM for what would have been Cain's first free agent year in 2012.  Based on Cain's latest extension, the Giants saved themselves at least $5-6MM by keeping Cain off the market in 2012.  Cain, of course, has greatly outperformed his extension on the field.
• Todd Helton.  The Rockies' star signed a two-year, $9.9MM extension for the 2012-13 seasons while also saving his team some money in the short term.  Helton was originally set to make $19.1MM in 2011 and faced a $23.6MM club option in 2012 that surely wold've been bought out for $4.6MM.  Instead, he earned $10.6MM in 2011 salary, with $13.1MM converted to deferred payments.  While Helton hasn't played well in 2012 at age 38, I still call this a minor win for the Rockies since they got some short-term salary relief and also made sure their franchise icon would retire in purple.
• Tim Lincecum.  "The Freak" was coming into his first arbitration-eligible year with unprecedented leverage, having won the NL Cy Young Award in both 2008 and 2009.  Lincecum asked for a record $13MM in 2010, with the Giants countering with an $8MM offer.  Both figures ended up coming into play, as Lincecum signed a two-year extension that paid him $8MM in 2010 and $13MM in 2011, plus a $2MM signing bonus.  It would've been a fascinating "what if?" to see if the arbitrator would've sided with Lincecum, and if he had, Lincecum probably would've been on pace to earn around $30MM in arbitration over those two seasons.  The Giants saved themselves anywhere between $3MM to $7MM on the Lincecum extension.
• Justin Verlander.  The ace righty isn't even halfway through his five-year, $80MM extension and yet it's already a deal the Tigers would happily do again.  Were it not for the extension, Verlander would've been a free agent last winter in the wake of his MVP-and-Cy Young-winning season.  He could've easily commanded a deal with an average annual value of at least $24MM per season, but Detroit has him locked up at $20MM per season from 2012-14.
• Carlos Ruiz.  The catcher signed a three-year, $8.85MM extension with the Phillies that covered all three of his arbitration-eligible seasons.  "Chooch" has been a great bargain for the Phillies, hitting .304/.390/.445 over the last three seasons and is currently enjoying his best year in the majors at age 33 — Ruiz has a whopping 1.038 OPS through 161 plate appearances.  The savings will continue for the Phillies since they hold a $5MM team option on Ruiz for 2013 that looks like a no-brainer pickup.
• Felix Hernandez.  Like Verlander's contract, Hernandez's extension covered his last two arb years and his first three free agent years, though the Mariners locked up their ace for $78MM, slightly less than what it cost the Tigers to extend Verlander.  Hernandez will earn $58MM from 2012-14, and had he reached free agency, he would've gotten at least $24MM per year on the open market and a return to Seattle would've been next to impossible.  Hernandez's deal is reasonable for a pitcher in his prime and he would net a huge trade return if the Mariners ever decided to deal him. 
• Shane Victorino.  The Phillies signed Victorino to a three-year, $22MM extension that covered his final two arb years and his first free agent year.  Victorino had a career-best performance in 2011 and would've earned at least $3.5MM more on the free agent market than the $9.5MM Philadelphia is paying him this season.
• Matt Kemp.  The Dodgers covered Kemp's first two arb-eligible seasons with a two-year, $10.95MM contract that guaranteed him $4MM in 2010 and $6.95MM in 2011.  Obviously it was a bargain performance-wise given Kemp's monster 2011 campaign, but Kemp's disappointing 2010 season would've brought down his 2011 arb number, so the Dodgers probably ended up saving maybe $1MM at most.  Then again, giving Kemp that early security was a sign that the Dodgers were committed to their center fielder, which may have been a factor in Kemp signing his eight-year, $160MM extension last winter despite the fact that the Dodgers hadn't yet solved their ownership problems.
• Tim Hudson.  Rather than pick up Hudson's $12MM club option for 2012, the Braves instead extended the veteran on a three-year, $28MM contract that includes a $9MM option ($1MM buyout) for 2013.  The Braves took a risk by extending a pitcher who was entering his age-34 season, but Hudson posted a 3.02 ERA and threw 443 2/3 innings in 2010-11.  His numbers are down a bit in 2012, but the Braves have already gotten a very good return on their investment.