San Francisco 49ers: Ranking the 10 worst free-agent signings in franchise history

ST. LOUIS, MO - NOVEMBER 1: Reggie Bush #23 of the San Francisco 49ers is carted off the field after being injured in the second quarter against the St. Louis Rams at the Edward Jones Dome on November 1, 2015 in St. Louis, Missouri. (Photo by Michael B. Thomas/Getty Images)
ST. LOUIS, MO - NOVEMBER 1: Reggie Bush #23 of the San Francisco 49ers is carted off the field after being injured in the second quarter against the St. Louis Rams at the Edward Jones Dome on November 1, 2015 in St. Louis, Missouri. (Photo by Michael B. Thomas/Getty Images) /
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9 Dec 2001: This is a close up of Jonas Jennings #75 of the Buffalo Bills. The picture was taken during the NFL game against the Carolina Panters at Ralph Wilson Statium in Orchard Park, New York. The Bills defeated the Panthers 25-24. Mandatory Credit: Rick Stewart/Getty Images
9 Dec 2001: This is a close up of Jonas Jennings #75 of the Buffalo Bills. The picture was taken during the NFL game against the Carolina Panters at Ralph Wilson Statium in Orchard Park, New York. The Bills defeated the Panthers 25-24. Mandatory Credit: Rick Stewart/Getty Images /

No. 6: Offensive Tackle Jonas Jennings

Signed in 2005 to a seven-year, $36 million contract

Remember this one, 49ers fans? If you do, it wasn’t pretty.

In fairness to San Francisco, the initial signing of veteran left tackle Jonas Jennings back in 2005 made perfect sense. He was coming off an impressive four-year start to his career with the Buffalo Bills and was one of the bigger-name free agents on the market. Plus, the Niners had just come off a woeful two-win season the year before and needed plenty of protection up front for their then first-year quarterback, Alex Smith.

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Jennings signed a massive seven-year deal, and the $36 million would still be a substantial amount over that period for an offensive lineman today.

Instead of being a problem solver, Jennings was an oft-injured problem. The San Jose Mercury News’ Daniel Brown described what led to his premature release in 2009:

"Jennings was supposed to be the stalwart left tackle to protect No. 1 pick Alex Smith. Instead, Jennings topped five games only once during his five four seasons with the 49ers. His year-by-year totals: 2005: 3 games 2006: 13 games 2007: 5 games 2008: 2 games Last year, a shoulder injury suffered against Seattle in Week 2 wiped out his season. Jennings worked hard to make a comeback — he didn’t like his reputation as fragile — but eventually surrendered to season-ending surgery."

Safe to say the multitude of injuries Jennings suffered resulted in the Niners never getting a return on their investment, leaving the 49ers O-line in a position to have to select an offensive tackle, Joe Staley, in 2007.

At least that latter move worked out well.