Earlier Saturday, the three Eye On Baseball writers discussed how much we'd pay Dodgers ace Clayton Kershaw in a contract extension, even though he's not a free agent until after next season. My colleague Dayn Perry argued that he'd wait until after the season because he wouldn't want to jump the gun and sign a guy early. And I couldn't help but think about Phillies first baseman Ryan Howard. It was April 26, 2010 when the Phillies signed Howard to a five-year, $125 million contract extension. He wasn't even set to hit free agency until after the 2011 season. And what an albatross of a contract that has proven to be thus far. Howard's contract began in the 2012 season, when he was recovering from a torn Achilles tendon. He was only able to play in 71 games, hitting .219/.295/.423 (91 OPS+). With the below average offensive production, poor baserunning and pretty much no defensive range, it's no surprise that Howard posted a negative WAR (-1.1). But he was hampered by injury and no one could have predicted that in 2010, right? Well, Howard was 30 years old when he signed the extension, which was for the seasons covering his age 32-36 seasons. Making Howard -- someone with essentially one skill: Hitting for power -- one of the highest-paid players in baseball for what would obviously be his decline years was a bad idea from the start. It's not like the Phillies are poor, either, so if Howard was coming off back-to-back MVP seasons and they really wanted to outbid the competition post-2011, they probably could have. Instead, general manager Ruben Amaro willfully saddled his club with an albatross. This isn't second-guessing. Many believed from the get-go it was a terrible deal or that at the very least the Phillies should have just waited. Look here, here, here, here and here. Howard managed 80 games this past season, hitting .266/.319/.465 with 11 homers and 43 RBI. Even if you want to double the power numbers to see what he might have provided in a full season, that's 22 homers and 86 RBI. This coming from a guy who doesn't get on base at a good rate, can't run well and plays sub-par (at best) defense. Again, he has one skill, and he's not even great at that anymore. This same guy is due $25 million in each of the next three seasons, when he'll be playing on a surgically-repaired Achilles tendon at ages 34, 35 and 36.