Crain earns $13 million under the teams of the contract, receiving $4 million in 2011 and $4.5 million in each of the '12 and '13 seasons. He joins Joaquin Benoit, Scott Downs and Matt Guerrier as free-agent relievers inked to three-year deals during this offseason, with Crain pointing to the White Sox offer of a third year as a deciding factor.
Guerrier and Crain were two of the late-inning forces in the Twins' bullpen. Now Crain will have to adjust to facing the only organization he has ever known since being selected in the second round of the 2002 First-Year Player Draft.
"I don't know how it's going to be. It will be weird," said Crain during a Monday afternoon conference call. "I've never been anywhere else. I'm good friends with a number of guys over there.
"They have an idea of what I do, and I have an idea of how they approach things. It will be fun, weird and interesting to face those guys so many times."
During an interview with KFAN Sports Radio 1130 AM in Minneapolis last week, Crain expressed a healthy dose of respect for his former employer. But make no mistake about it: Crain is "ecstatic," to invoke his description, to be part of the White Sox.
Williams and the White Sox employed their typical quick-strike, under-the-radar approach to bring Crain to Chicago. Crain's camp was engaged in significant talks with the Rockies and also had talks with the Red Sox, before the White Sox came into the picture on Tuesday.
This deal only took 24 hours to basically finalize. It was three days prior to this initial exchange of offers when Williams told MLB.com how the team actually had more money to spend to fill a bullpen vacancy, after Williams talked of the team being tapped out at the Winter Meetings, and he quickly put it to good use.
In 71 appearances for the Twins last year, Crain posted a 1-1 record with a 3.04 ERA. He tied for the eighth in the AL with a career-high 21 holds and limited opponents to a .215 average, including a .196 average for left-handed hitters.
His ERA sat at 5.26 on June 13. But Crain began a stretch of 21 consecutive scoreless appearances on June 12, covering 20 innings and ending on Aug. 4. He put together a 0.28 ERA in 35 games from June 10 until the close of August, allowing just one earned run over 31 2/3 innings.
Working in pitcher-friendly Target Field stands as a bit more inviting than coming in with the game on the line at U.S. Cellular Field, especially when the ball jumps off the bats during warm summer months. Crain doesn't seem intimidated by the ballpark, nor does he seem to be affected by the weight of expectations coming with this new deal.
There will be times when Crain gets beat, and there will be times when fans get on him. It's all part of the job, from Crain's point of view, with a short memory always serving as key for a late-inning reliever.
"That's what I'm going to try to do, just try to not to let other things factor in," said the laid-back and confident Crain. "You start thinking too much, and you start struggling.
"Through the ups and downs, peaks and valleys, you have to keep the same mindset every day and stay on an even keel. This is just a game we play and you try not to think about the other stuff, but I feel like I deserve [this deal) and worked really hard to get here."
Along with the third year, Crain's chance to close played into his White Sox selection. Rookie Chris Sale and Matt Thornton appear to be the White Sox best options from the left side, but if a right-handed closing option is needed, Crain figures to get the call from manager Ozzie Guillen.
Closing was on the agenda for Crain in Minnesota heading into the 2004 season, before the Twins acquired Nathan in the Pierzynski trade. Crain will be throwing to Pierzynski with the White Sox.
"You know, asking for my opinion right now, on Dec. 20, I'm going into it saying Jesse Crain, and this is just my thinking, he's going to be a valuable member of the bullpen late in the game," White Sox pitching coach Don Cooper said. "More than anything, what he gives us is not just another valuable piece, but a talented, flexible piece."
Flexibility and talent clearly were not enough to keep Crain with the Twins, who Crain said made it clear they weren't going over two years or $3.5 million per season. Instead, the Twins probably will follow a practice of filling from within, with names such as Pat Neshek, Alex Burnett and Anthony Slama emerging as bullpen candidates.
Meanwhile, Crain will be trying to go "all-in" with his new team in pursuit of a championship.
"We have a chance to go to the World Series," said Crain of the White Sox. "I'm really excited and feel like I'm only getting better."