Baltimore Orioles' Worst Free-Agent Contracts of All Time

As Homegrown Stars Like Matt Wieters and Manny Machado Thrive, a Look Back at Birdland's Biggest Busts

Yahoo Contributor Network

COMMENTARY | For decades, the Baltimore Orioles were a model major-league franchise, drafting and developing prized talent like Cal Ripken Jr, Mike Mussina and Gregg Olson. After a decade of writing huge checks to underachieving imports, it appears the O's are ushering in a new age of the Oriole Way with superstars like Manny Machado and Matt Weiters.

Here's a look back at the the biggest free-agent busts in the Baltimore Orioles' history, including the biggest blunder from this year:

5. Jair Jurrjens

After a magical postseason run, the Orioles were scrutinized for not bringing in big-name talent to capitalize on the club's first winning season in over a decade. Instead, the O's scoped out potential bargains, inking Atlanta starter Jair Jurrjens to a $1.5 million deal. However, after a physical, the contract became a minor-league pact, and the Birds pulled a lot of money off the table. Jurrjens failed to make the team out of spring training and lasted just 5 innings in his Orioles debut, surrendering 4 runs in the process. He was recently optioned to Triple-A Norfolk.

4. Steve Kline

Steve Kline was a bullpen stalwart for the 2004 St. Louis Cardinals, helping the club reach the World Series with a stellar 1.71 ERA. The Orioles gave him $5.5 million over two years to change feathers. Kline struggled in Baltimore, blowing two games before telling a St. Louis newspaper that he was miserable in Charm City, and wished he had a genie to send him back to his old club. Fans quickly turned on him, and Kline did little to help his own cause on the mound. He balked home a winning run -- twice -- on his way to a career-worst 4.28 ERA. The O's jettisoned the lefty to San Francisco after one season.

3. Rafael Palmeiro

Signing Rafael Palmeiro in 1993 was one of the greatest moves in franchise history, but bringing him back in 2004, however, ended in disaster. In his first tour of duty, Raffy crushed 182 homers over five glorious years, powering the Birds to two playoff appearances, which included a division championship.

His homecoming was supposed to provide a storybook ending to what appeared to be a Hall of Fame career, but as Palmeiro struck his 3,000 major-league hit, storm clouds brewed above the confetti at Camden Yards. In 2005, he became the most prolific pro busted by the league's new performance-enhancing drug tests, infamously declaring his innocence to a Congressional panel with poignant finger jabs five months before news of his flunked test broke. Palmeiro's fall from grace proved to be one of several factors that contributed to the club's historic collapse in 2005. Following a lengthy stay atop the division, Baltimore imploded, posting a 27-48 record after the All-Star break.

2. Sidney Ponson

In July of 2003, the Orioles traded starting pitcher Sidney Ponson to the San Francisco Giants in in the midst of the homegrown starter's first winning season in the majors. The following winter, Ponson was welcomed back to Baltimore with a handsome free-agent contract worth $22.5 million over three years. Ponson quickly started making headlines -- but for all the wrong reasons.

In 2004, the O's new ace was jailed in his native Aruba for punching a judge, with two DUI arrests following shortly after. On the diamond, the Aruban Knight pitched like a court jester, going 18-26 with a 5.64 ERA in two seasons. The club released him in 2005, but Ponson remained a thorn in Baltimore's wing until his contract grievance was finally settled four years later.

1. Albert Belle

Once upon a time, Albert Belle was one of the most feared hitters in MLB. In 1999, the Orioles made Belle the wealthiest player in the game with a five-year, $65 million deal. The cantankerous right fielder hit 60 home runs with 220 RBIs over two seasons while clashing with management. A degenerative hip condition forced Belle in to early retirement, and the money left on the contract crippled the Orioles for years to come. ESPN ranked Belle No. 4 on its list of the worst free-agent signings of all time.

Mateo Samper is a sports blogger and freelance writer. He graduated from Salisbury University with a degree in journalism, and is a lifelong follower of the Baltimore Orioles. Follow him on Twitter @MatroStation.

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