Joey Votto

In extending Ryan Braun and Troy Tulowitzki through the year 2020, the Brewers and Rockies made bold commitments to their young stars by adding multiyear extensions on top of pre-existing contracts that already covered both men through 2015 and 2014, respectively. 

Are these deals risky?  Absolutely, but the contracts represent the latest step in how clubs attempt to lock up their young stars.  It isn't enough to just gain cost-certainty on a player through his arbitration and first few free agent years.  If a team feels they have a true franchise player, it won't hesitate to sign that player to what essentially could be a lifetime contract in order to (hopefully) avoid spending even more money to re-sign that player or a comparable star as a free agent.

Should other clubs look to explore this tactic of extending an extension, here are some of the possible candidates to join Braun and Tulowitzki in the "2020" club.

• Evan Longoria.  We start off with the man with arguably the most team-friendly extension in baseball history.  Longoria's six-year, $17.5MM contract signed in April 2008 contains three team option years (worth $7.5MM, $11MM and $11.5MM, respectively) that could keep him in Tampa Bay through 2016, his age-29 season.  As MLBTR's Mike Axisa pointed out over the winter, however, the Rays' uncertain financial situation makes it unlikely that they would make an even longer commitment to Longoria than they already have. 
• Robinson Cano.  Cano signed a four-year, $30MM extension before the 2008 season that also includes team option years for 2012 ($14MM) and 2013 ($15MM).  New York will obviously keep Cano in the fold through his age-30 season by picking up those two options, unless those years get replaced by a longer-term contract.  Cano hired Scott Boras as his agent in February and while Cano said he isn't planning to ask for an extension before his current deal expires, the second baseman is clearly already thinking ahead.
• Justin Upton.  The first overall pick of the already-legendary 2005 draft is signed through 2015 on a six-year, $51.25MM extension that will run out when he's 28 years old and right in the middle of his prime years.  The Diamondbacks explored a few deals for Upton over the winter and set off a flurry of speculation, but it appears as if GM Kevin Towers was simply doing his due diligence to see if another team would go overboard with a trade offer.  Upton had a slightly disappointing (.799 OPS) 2010 season, so Arizona might wait for at least one more superstar campaign from their young star to make sure he's worth the risk of another multiyear extension.
• Hanley Ramirez.  It seems odd to think of the Marlins doling out any major extensions, let alone two to the same player.  With the team moving into its new Miami ballpark next year, though, the extra revenue could make another multiyear deal for Ramirez into a reality — not to mention generating some goodwill amongst Marlins fans to get them to spring for season tickets. Ramirez is under contract through 2014 on a six-year, $70MM deal and 2015 will be his age-31 season.  If Florida did explore an extension for Ramirez, they would surely have to factor in a move away from shortstop, since his defensive woes (a career -9.4 UZR/150) are likely to worsen as he ages.
• Ryan Zimmerman.  MLBTR's Ben Nicholson-Smith recently outlined how the Nationals' previous extension with Zimmerman — a five-year, $45MM pact that runs through 2013 — was a terrific bargain for the club.  Given Zimmerman's production, age (he'll be 29 when his deal runs out) and Washington's willingness to spend, Zimmerman is probably the most likely player on this list to receive a Braun/Tulowitzki-esque deal.
• Joey Votto.  The Reds took the first step towards locking up the reigning NL MVP when they signed Votto to a three-year, $38MM pact that covered the first baseman's arbitration years.  Votto is still on pace to hit free agency as a 30-year-old in his prime, and as one agent put it, "the Reds took on all the risk" with this initial deal.  Cincinnati has put itself in position to contend over the next few seasons, so that will theoretically take care of the Great American Ballpark's attendance problems and make it possible for the team to get Votto signed to an even longer-term contract.
• Miguel Cabrera.  Cabrera signed an eight-year, $152.3MM extension with the Tigers before the 2008 season.  He'll turn 33 in 2016, and that advanced age plus his off-the-field issues make him an unlikely extension candidate.  Detroit has the money and Cabrera has put up Cooperstown-worthy numbers throughout his career, but there just may be too much risk involved for the Tigers to commit more money to the slugger.