Before being traded to Boston last month, the pitcher had been included in transactions on two previous occasions, going from the Reds to the Blue Jays to the White Sox and, finally, to the Red Sox.
While he was once packaged in a trade for Scott Rolen — in August 2009 — the 25-year-old PawSox pitcher was honored that he was acquired in exchange for third baseman Kevin Youkilis.
"That's a big deal," Stewart said. "It's one of those things that kind of tell you the organization puts stock into you with them trading [away] a guy that big. He's a great player that had a great career. So to be traded for a guy like that, it does say a lot. It tells me what I have to do to make it worthwhile."
Shortly after the trade was finalized, Red Sox general manager Ben Cherington said he envisioned Stewart as a possible starter. Through three appearances for Pawtucket, Stewart has delivered a promising return on the investment.
He's savoring that success, despite getting re-acclimated to a starting role. With the White Sox, Stewart pitched out of the bullpen, recording a 6.00 ERA and 1-2 record in 18 appearances for Chicago.
"It hasn't been too bad," Stewart said of the adjustment. "[PawSox pitching coach] Rich [Sauveur] has helped me out a lot with pitch counts and stretching me out. They've been really open with everything. It's been pretty easy other than throwing more pitches in a game. That's the hard part."
In two stints in the majors — with Toronto and Chicago — Stewart has amassed a 3-8 record in 31 appearances, those of those starts. He's looking to reclaim the promise that made him a third-round pick in the 2008 MLB Draft.
Since joining the starting staff, he's posted a 1-0 record with a 1.96 ERA to go along with five strikeouts. And Stewart believes he can bring that type of consistency to the Red Sox organization.
"I throw a lot of strikes," Stewart said. "I don't walk a lot of guys. That's always pretty much been my thing –– nothing too flashy or too crazy. Just trying to get guys out and do it in an efficient fashion."
Either way, he'll be forever tied to Youkilis.