Right-handed reliever Dewon Day was on vacation in New York City last fall, about to go out with a friend to watch an American League Championship Series game between the Boston Red Sox and Tampa Bay Rays.  

  Though the Rays had already eliminated his own team, the Chicago White Sox, in the first round of the playoffs, Day was still cheering for the Rays. After all, one of his best friends, shortstop Reid Brignac, was with the club.  

    Then Day’s cel phone rang and he got the news.  

  He’d just been claimed on waivers by the Boston Red Sox. 

  “I was like, ‘Damn, I don’t know who to cheer for now,'” he laughed, recalling the night.  

  It was the second time that Day, now 28, had changed organizations. And it wouldn’t be the last time.  

  Though he never threw a pitch in a Red Sox uniform, he participated in the organization’s winter Rookie Development Program that January, spending time with the coaches and the players he thought would be his future teammates.  

  “I really liked everything they did with that organization, how they treated their players on and off the field really wowed me,” he recalled. “But while I don’t usually really keep up with that stuff, I pay some attention to transactions and I noticed they were signing a lot of free agents.” 

  Enough so that one day after lunch, when he saw farm director Mike Hazen approach him, he had an idea what was up.  

  “I knew what time it was,” he laughed. “They told me that they had designated me for assignment and that I’d been claimed.” 

  By the Tampa Bay Rays.  

  This marked Day’s third American League East club since he’d turned pro in 2003.  

  Originally drafted out of Southern University in 2002 by the Toronto Blue Jays, the lanky Mississippi native had struggled through the good and the bad in his first few pro seasons. His electric arm showed flashes of brilliance, his slider was nasty, but elbow trouble kept him from reaching his full potential.  

  He’d posted a 1.80 ERA and 12 saves in his pro debut at short-season Pulaski in ;03 and a 1.50 ERA at short-season Auburn, one level higher, the next summer, limiting New York-Penn League hitters to a .184 average but his 2005 campaign was a lost summer due to injury.  

  That winter, the Jays left him unprotected and the White Sox took a flyer on him, selecting him with the last pick in the Minor League Rule 5 draft. 

  Now healthy, he posted a 3.40 ERA that summer in 40 games at Advanced A Winston-Salem and had a 3.60 ERA with 48 strikeouts in 25 innings the next spring with Double-A Birmingham when he got the most unexpected call: he was going to the big leagues.  

  His trip to the big leagues was a mixed bag over two months, showing flashes of his potential but also some control problems. He also had a stint on the DL and eventually returned to the Minors, this time to Triple-A Charlotte.  

  Day made up for lost time in the Arizona Fall League where he posted an impressive 1.38 ERA in 11 games, striking out 17 while walking just four over 13 innings, but there was no return to the Majors in 2008.  

  After he posted a 4.56 ERA in the bullpen at Charlotte, the Sox decided to see how he’d do as a starter and it was back to Birmingham to work on that transition. It wasn’t one he really wanted to make.  

  “Changing roles was like starting all over again,” he said. “It was so frustrating. I didn’t want to be a starter. I’d never thrown more than one or two innings at a time. But my biggest fear had always been failing and once you do, you realize it’s not that bad because at least you’re still playing. So I think I’m better now for the experience.” 

  The move over to his new organization was made easier by already having friends there. In fact, when he was with Charlotte and the team would travel to Durham, Day would stay with Brignac at his house there. And coincidentally, Day already had travel plans made to go to Tampa Bay to hang with his buddies for Super Bowl festivities.  

  “I told Reid even before I told my parents and he thought I was kidding,” said Day.  

  Though Day did not stick on the Rays’ 40-man roster, he made an impression in spring training, posting a 1.80 ERA in three games before being reassigned to the Minors where he will more than likely break camp in the Durham bullpen.  

  He could not be happier with his new organization.  

  “Every single day here has been fun, because it’s a really loose clubhouse where everyone is nice, everyone jokes around,” he said. “But what makes it so good are the coaches. They are all great. And Joe Maddon is the coolest manager I have ever been around.” 

MLB: Of what accomplishment, on or off the field, in your life are you the proudest?  
Dewon Day: On the field it would have to be going to the big leagues after everything I went through, being pretty much in rookie ball for three years. But if you ask me this question again in three or four months, it will be finishing my college degree through the University of Phoenix online. I won a scholarship last year. I think my mom will be even happier about it than I am.  

MLB: What do you think you’d be doing now if you weren’t playing baseball?  
DD: When I went to college I was a nerd so I’d probably be dong something with numbers, probably an engineer.  

MLB: Do you have other hobbies or creative outlets aside from baseball? 
DD: I love playing chess. I picked it back up last year. I don’t play in the clubhouse, I play on my iPod. And I shoot pool a lot.  

MLB: Complete this sentence: It would surprise people to know that I…  
DD: I’m a mama’s boy. People who know me personally know that but others would probably never guess it. And it will make her smile when she reads this. Also, I love to go to the mall and shop for hours. I’m addicted to buying jeans.  

MLB: Who would play you in the movie of your life? 
DD: Donald Faison (“Scrubs,” “Clueless”). Here in Tampa we were out one night and a bartender kept saying ‘I know you, you’re an actor,” and I kept saying no She kept on, because she thought I was lying and just didn’t want to admit it. She was like “You’re that guy from ‘Clueless’ but you look cuter in person than you do on TV.” I finally had to show her my driver’s license.  

MLB: Which aspect of life in the minors has surprised you the most, in comparison to what you might have imagined before you turned pro?  
DD: We stayed in some pretty bad hotels and had some bad clubhouses, especially in the Appalachian League. In a few places, if you weren’t the first person in the shower you were in standing water.