As of right now, Yovani Gallardo is the only player on the Brewers' 40-man roster without a contract for 2010. He appears to be heading for another contract renewal, but thankfully he isn't making a big stink about it (unlike Prince Fielder, who had a problem with the renewal process the year after he hit 50 home runs). An interesting note in Adam McCalvy's post on the subject: the Brewers have actually had brief talks about a multi-year extension for Gallardo but were unable to find common ground.
As great as it would be to lock Yo into a long-term, team-friendly deal like Ryan Braun's, I just can't come around to thinking it would be a good idea. For Braun, it was a no-brainer. He's an everyday player, and everyday players are much, much more likely to live up to their contracts and stay healthy. We've seen that with Braun -- aside from the freak intercostal strains that flare up from time to time, he's been in the lineup nearly every day.
A long-term extension for a pitcher is a riskier business venture. The Brewers (and their fans) know this all too well. Teddy Higuera? Ben Sheets? Those extensions seemed like a great idea at the time, only to leave bad tastes in our mouths afterwards. We've had such bad luck with pitching prospects in the minors that it seemed like a minor miracle that Yo made it to the big leagues and lived up to the hype, and we still saw him suffer a freak injury that cost him almost a full year.
The Brewers are far from the only team that have become a little trigger-shy when it comes to giving pitchers long term deals. Heck, Tim Lincecum has won the past two Cy Young awards, and the Giants would only commit to a two-year extension for him. If the Brewers aren't going to go year-to-year with Gallardo, I would hope they take a page from the Giants' book -- no more than a two-year extension for the time being, and wait until he reaches his first arby-eligible year.
In other words, finish out this season with him making close to the minimum, then hammer out a deal this winter to avoid arbitration. You can always tack on another year or two after next season, but any more years than that would likely prove to be another bad gamble for Doug Melvin, especially when you already have Randy Wolf locked into a big-money deal during the same timeframe. There's really no rush to get Gallardo signed to a long-term deal -- he's under team control until 2013, and unless the team anticipates a large gap between their offer and his demands in arbitration, there probably isn't even a reason to do a long-term deal beyond cost certainty for a couple seasons.
A two-year deal would sort of be the best of both worlds in that regard. Assuming a deal following this season, you'd likely have him locked up for 2011 and 2012 at a reasonable salary, and without as much risk. Sure, another season-ending injury could mean you're paying him millions to be on the DL, but with him in his arby years now, you're going to be doing that anyway.