Cubs general manager Jim Hendry described the move as "high risk, high reward." The biggest concern was how many games Bradley would play because of his history of injuries and not his controversial past. Ron Washington, who was Bradley's manager in Texas in 2008, praised the outfielder, saying the only problem was that he was a perfectionist.
But Bradley's one season in Chicago was anything but perfect.
The switch-hitter's tumultuous tenure with the Cubs ended on Friday when he was traded to the Mariners for right-handed pitcher Carlos Silva and cash.
The transaction needed approval by Major League Baseball because of the money involved. After taking both players' contracts into account, the Cubs will receive $6 million from the Mariners in addition to Silva.
"We have been looking to add offense to our club and in Milton have a player who has always gotten on base and has the ability to drive in runs," Mariners general manager Jack Zduriencik said Friday. "He is passionate about winning, as we are, and we believe he'll be a good fit here."
At least three teams expressed an interest in Bradley, and one rumor had him going to Tampa Bay in exchange for Pat Burrell. There also were rumors Bradley would be reunited with Washington in Texas. Hendry and Zduriencik didn't talk about a deal until two days ago.
"We knew we had to move the player," Hendry said Friday of Bradley. "In hindsight, obviously, it was an acquisition that I'm responsible for that obviously didn't work out."
The Cubs originally signed Bradley, 31, because they wanted a left-handed bat to break up the overload of right-handed hitters such as Aramis Ramirez, Derrek Lee, Alfonso Soriano and Geovany Soto. In 2008, Bradley led the American League in on-base percentage, batting .321 with 22 homers and 77 RBIs. With the Cubs coming off a 97-win season in '08, Bradley looked to be the final piece needed.
But he struggled, hitting .257 with 12 homers and 40 RBIs for the Cubs, and was suspended for the final 15 games of the season because of detrimental conduct. Hendry sent Bradley home on Sept. 20 following comments to the Daily Herald (Arlington Heights, Ill.) newspaper, which included Bradley saying, "You can understand why [the Cubs] haven't won in 100 years here, because it's negative."
Hendry's response: "The only real negativity here is his own production."
The day before, Bradley had engaged in a shouting match with then hitting coach Von Joshua when asked if he was available to pinch-hit.
In June, Cubs manager Lou Piniella also had a nasty verbal exchange with Bradley during an Interleague game at U.S. Cellular Field, and sent the outfielder home. With the media, Bradley could provide intelligent, in-depth answers to questions, and the next day, snap a retort.
The Mariners will be Bradley's eighth Major League team since he broke in with Montreal in 2000. Hendry said he did his homework before giving Bradley a three-year deal. Why didn't this work?
"When we [signed him], I think everybody still felt like we were favored to win the Central," Hendry said. "He was coming off a terrific year. It's hard to find a guy who can really hit, has some power and a high on-base percentage like he has. We were swept two years in a row [in the playoffs] by good right-handed pitchers.
"The bottom line is he got off to such a bad start, and the expectations were so high for all of us, and when the expectations weren't met and the criticism started in his direction, I don't think he handled it well," Hendry said. "Once you go down that path, we're playing on the big stage, and if you want the big stage you have to be able to perform on the big stage."
Hendry may be shouldering the blame, but it would seem that Bradley also needs to look in the mirror and accept some responsibility as well.
"I always look at myself first," Hendry said. "My intentions were going for levels higher that we were close to and hadn't reached. I think every player will tell you they're responsible for their own performance.
"I would think he'd think he should've performed better," Hendry said. "I'm not here to speak for him."
The Cubs had several players beyond Bradley who didn't peform up to expectations in 2009, including Soriano, Soto, Carlos Zambrano and Mike Fontenot. The end result was a second-place finish in the National League Central, and even though the Cubs had a winning record, it was a difficult season.
Moving Bradley was beginning to seem impossible, but Hendry found a match with Seattle, which was trying to unload Silva. The veteran hurler has two years remaining on a four-year, $48 million contract, which he got prior to the 2008 season from former Mariners general manager Bill Bavasi.
Bradley is owed $21 million over two years -- $9 million in 2010 and $12 million in '11. Silva has $25 million remaining on his deal -- $11.5 million in both '10 and '11 and a $2 million buyout on a '12 option.
"It's unfortunate," Cubs pitcher Ryan Dempster said in September after Bradley was suspended. "At the end of the day, he was provided a great opportunity to come over here and be a part of a really great organization with a lot of really good guys, and it just didn't seem to make him happy, anything."
Carrie Muskat is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.