11. Adam Podlesh-Punter-Free Agent 2011: Chicago's previous punter Brad Maynard had a successful ten-year run with the Bears after he was signed away from the New York Giants prior to the 2001 season. Maynard provided precision pinning of opponents inside their 20 yard line, if not big leg strength. But as of 2011 it was clear the next player at the position needed to be identified. Podlesh was a young player that was successful in Jacksonville, and Angelo targeted and acquired the player when needed. It may be surprising to some to see a punter listed anywhere in a top acquisitions list, but all the reader must do is recall the tenure of second-round draft pick Todd Sauerbrun in 1995 to remember that punters do matter. Sauerbrun posessed a booming leg, possibly the greatest for a punter in the NFL since the legendary Ray Guy. But during his rookie season, several Sauerbrun shanks actually contributed to losses in a season in which one more victory would have earned the Bears a playoff berth. So at least at this position, Angelo left the Bears in good hands for years to come.

10. Ricky Manning Jr.-CB-Free Agent 2006: The Bears returned to the playoffs for only the second time in eleven years in 2005. They hosted one of the NFC Divisional Playoff games that season, and in this one appearance they were shocked at home in a loss to the Carolina Panthers. The main reason? Carolina receiver Steve Smith caught passes for over 200 yards against a shaky Chicago secondary. During the game the Bears fielded several abysmal reserve defensive backs, including Rashied Davis, a player that would be converted to play wide receiver the following season. So in order to contend the following season Angelo needed to upgrade the defensive secondary. In addition to drafting safety Danieal Manning that year, Angelo also targeted a member of the Panthers that had helped Carolina embarrass Chicago at home, defensive back Ricky Manning Jr. Manning was a restricted free agent, tendered at the level that required the Bears to forfeit a third-round pick for the signing, and the Bears did so. In one of Angelo's notable red flag moves, it was later revealed that Manning participated in an assault in Los Angeles shortly after signing a lucrative contract with the Bears. Manning was a solid contributer in 2006, becoming the nickel back, a critical position in Smith's defense. He proved to be a playmaker, intercepting five passes and returning one for a touchdown during the Super Bowl run. Manning's play tailed off in 2007, and he was released in 2008. But for his contributions in the special 2006 season, Manning makes the list of good acquisitions.

9. Muhsin Muhammed-WR-Free Agent 2005: Following his departure from the Bears in 2008, Muhammed uttered a famous quote that "Chicago is where receivers go to die." Until 2012 at least he may be correct, but even prior to the opening of free agency in 2005 Angelo pounced to sign Muhammad after his release from the Panthers for salary cap reasons. Muhammed had set a Super Bowl record for the longest touchdown reception in 2003, and in 2004 led the NFL with 16 touchdown receptions. The receiver provided solid if unspectacular play for the Bears in 2005 and 2006, as well as leadership. But by 2007 it was clear his skills were declining. Had Muhammed stuck longer and contributed more his name would be much higher on this list.

8. Ruben Brown-G-Free Agent 2004: Former Bears guard Chris Villarrial was a fixture at the position from 1996-2003, but he was entering unrestricted free agency in 2004, and the Bears chose not to match the Buffalo Bills' big-money offer. Instead they chose to sign Buffalo's castoff at the position, Ruben Brown, who had played in eight consecutive Pro Bowls for the AFC. Brown was a Buffalo cap casualty, then endured an inauspicious start in Chicago when he started just nine games before being placed on injured reserve. In 2005 he played in 12 games, missing four in the middle of the season with a chest injury. Angelo's investment in Brown paid off in 2006, when during the Bears' Super Bowl run he started all 16 games and was named to his ninth Pro Bowl. 2007 was the end of the road for Brown, while much of the rest of the Bears' offensive line crumbled around him. Brown played in the team's first eight games before being placed on injured reserve again with a shoulder injury. Brown played solidly for the Bears when healthy, and would have been listed higher here had his Chicago career been longer.

7. Robbie Gould-K-2005: Kickers are certainly important. When a team finds a great kicker, they can be critical to a team's success. When a kicker is bad, it greatly impacts the team's fortunes. But kickers are usually acquired late in the draft if not as undrafted free agents, so despite the fact that Gould is knocking on the door of being the best kicker in Chicago Bears History, it's still hard to rank this acquisition higher than seventh. For the Bears, Kevin Butler provided a legendary presence for the Bears from 1985-1996. When Dave Wannstedt chose to release Butler prior to the '96 season, he replaced the legend with a scrub named Carlos Huerta who was sacked following a 3/7 start to the season. Then veteran Jeff Jaeger was brought in and was solid for three seasons. Injuries forced the Bears to replace Jaeger with Chris Boniol in 1999, and during that year the Bears joined the bad kicker club, with Boniol blowing the opportunity to win several games. Paul Edinger was drafted and played capably from 2000-2004, but for some reason fell out of favor with the regime despite delivering some clutch kicks. Edinger's replacement in 2005 was veteran Doug Brien. But the usually solid Brien delivered a Huerta/Boniol-type performance to start the 2005 season, so coach Lovie Smith and Angelo set up a "kick off" between Brien and several auditionees, including rookie Robbie Gould. Gould had not stuck with any team in 2005 and was called in from a construction job to compete. Gould was quickly signed. Author's note: when Gould was signed, even after he performed solidly in 2005, I thought that perhaps Gould could simply hold down the job until Edinger could be re-signed if he didn't work out in Minnesota (who had signed him to a lucrative contract), or perhaps Ryan Longwell could be brought in from Green Bay when he hit free agency. How wrong I was, as Gould is currently the fifth most accurate kicker in NFL history with an 85.7% percent accuracy rate over his seven NFL seasons. Gould's knock has always been his lack of leg strength, and through most of his career he has rarely been trotted out to attempt kicks over 45 yards. But in 2011 Gould defied his critics by hitting an astounding six of six attempts over 50 yards. Gould was a gem of a signing by Angelo.

6. Roberto Garza-G-Free Agent 2005: Garza was signed as a free agent by Angelo prior to the 2005 season. At the time the Bears were grooming 2002 third-round pick Terrence Metcalfe to take the starting right guard job, and the signing of Garza was widely panned as Garza had suffered knee injuries and was missing cartlidge. Sign an offensive lineman that was missing knee catrlidge? Smooth move, Jerry (it was thought at the time). Despite the concern, Garza became an immediate starter on the Bears offensive line in his first season, replacing Metcalfe after 11 games, and has never looked back. As of 2011, when Garza switched to center from guard, Garza has been one of the most stalwart interior offensive linemen in Chicago Bears history. As well as appearing to be a really good guy.

5. Adewale Ogunelye-DE-Trade 2004: Lovie Smith's defensive system demands a pass rush, and a pass rush usually requires at least one stud pass rusher. In 2004 the Bears invested heavily in tackles Tommie Harris and Tank Johnson in the first two rounds and later Claude Harriot in the fifth, but Alex Brown wasn't going to cut it as the top defensive end. In arguably Jerry Angelo's biggest trade splash to that point, the general manager shocked fans by pulling off a trade on the day of Chicago's first preseason game. Angelo sent wide receiver Marty Booker and the Bears' 2005 third-round draft pick to the Miami Dolphins for Ogunelye, fresh off a 15-sack season opposite end Jason Taylor in 2003. Ogunelye had been holding out for a new contract, one which Miami's leadership including coach Dave Wannstedt would not provide. Acquiring a young, proven pass rusher for an average receiver and a third-round pick was a great move for Angelo and the Bears. Ogunelye spent the majority of his first season with the Bears injured, after he had signed a six year contract worth more than $33 million. His play was solid as the Bears top defensive end in 2005 and 2006, helping lead the Bears defense to top-five rankings in those playoff seasons. But like many of his teammates, his play declined following the 2006 season. He was not re-signed when the six-year contract he signed in 2004 expired.

4. Thomas Jones-RB-Free Agent 2004: Jerry Angelo arrived in Chicago just months after his predecessor Mark Hatley made Michigan running back Anthony Thomas the team's second-round pick. Despite Thomas leading the Bears' offense that year and becoming the team's first Offensive Rookie of the Year since Gale Sayers, Angelo stated after the season that he didn't believe Thomas was a franchise running back. (Obviously this was a statement that didn't sit well with Thomas). Thomas had an injury-plagued sophomore season, then rebounded a bit in 2003. But with the arrival of Lovie Smith and offensive coordinator Terry Shea, who was installing an offense similiar to that run by Mike Martz in St. Louis and Al Saunders in Kansas City, Angelo went shopping for a Marshall Faulk or Priest Holmes (the backs that enjoyed success in the aforementioned cities). Luckily for the Bears, Jones was coming off a season that had resurrected his career. Jones was a top-ten draft pick of the Arizona Cardinals in 2000 but never distinguished himself. He had been traded to Tampa in 2003 for a song, and burst out with speed and power in limited duty with tthe Buccaneers. Thus on the first day of free agency the Bears pitched heavy for Jones and signed him to a four-year contract to replace Thomas as the starter. Jones did not disappoint in his first season with the Bears. Despite missing several games with injuries, Jones totaled more combined yards by any running back in Chicago since Neal Anderson. In 2005 and 2006 he was the workhorse behind the Bears' offense. His speed was obviously down from what it was earlier in his career, but his strength was up. The only problem in Jones' Bears tenure was that curiously, Angelo decided to draft troubled Texas running back Cedric Benson with the fourth overall pick in 2005, ostensibly because new offensive coordinator Ron Turner demanded a bigger workhorse back in his system. Benson and Jones shared time in the backfield for two seasons, but did not share any camaraderie. Following the 2006 season in which the Bears went to the Super Bowl and Jones rushed for 1,210 yards, the Bears determined it was time for Benson to have the job to himself. Jones was traded to the New York Jets in exchange for flip-flopping second-round picks in the 2007 draft. (A move that netted the Bears nothing, since those picks resulted in Chicago drafting Dan Bazuin and Michael Okwo, two players that never played a down). And Benson failed in his one year as the starter before being cut.

3. John Tait-T-Free Agent 2004: Throughout Jerry Aneglo's Chicago Bears tenure as General Manager, from start to finish, he had a track record of tinkering with "projects" at the critical position of left offensive tackle. The left tackle on the offensive line is the most critical position, as this is the lineman that needs to seal the outside edge of the pass rush on the (usually) quarterback's blind side. Play a scrub at left tackle and quite frequently your team's quarterback will end up on his face. Not a good thing. To his credit, Angelo used his first draft pick as a general manager on a tackle when he selected Boston College's Marc Colombo in 2002. Unfortunately for Angelo (and Colombo), as a rookie the top pick suffered a devastating knee dislocation and would never again play meaningful football with the Bears. Then in 2003 and 2004, Angelo experimented with a young undrafted free agent named Quasim Mitchell at the position. Angelo thought his evaluations pointed to Mitchell having the physical skills to be able to play solid football at the position. Mitchell was known to be the starter on the left side going into the 2004 season, but new offensive coordinator Terry Shea stated his philosphy required "two left tackles" (two with the athleticism required to play on the left side rather than a road grader on the right, as many teams employed). And the Bears indeed had a road grader on the right side in 2003 in a former Detroit Lions first round pick, the nearly 400 pound Aaron Gibson. So in free agency the Bears pursued Kansas City Chief restricted free agent John Tait. The Bears struck immediatedly, signing Tait to a massive six-year contract the Chiefs declined to match. Tait started at right tackle through the 2004 season while Mitchell suffered on the left. In 2005 it was decided that Tait would move to the left side after the release of Mitchell, and Tait remained the key piece of the Bears' offensive line until he abruptly retired prior to the 2009 season, with a year remaining on his contract. As of this writing in 2012, Angelo again had allowed an unorthodox solution at the critical position by starting seventh-round pick J'Marcus Webb through the 2011 season to mixed results. Time will tell if the legacy he leaves at this critical position works out or not.

2. Julius Peppers-DE-Free Agent 2010: The Chicago Bears organization over the years has been known as a cautious one. Rarely does the organization rush to sign the top free agent of any given year, thus setting the bar for the NFL. Much more frequently they proceed with caution, only signing known commodities to team-friendly contracts. In fairness to the Bears, this could be due to their history of striking out when they have set the bar (Bryan Cox in 1996, which turned out to be a disaster). Entering free agency in March 2010, Carolina Panthers defensive end Julius Peppers was agreed to be unquestionably the top free agent available. A stud pass rusher is coveted in any defense but especially in Lovie Smith's, which requires a strong pass rush being generated by down linemen with little reliance on blitzing. Adewale Ogunelye had served as the Bears' top pass rusher for six years, but by the end of 2009 it was clear he had little left in the tank and would not be re-signed. Peppers was the second overall pick in the 2002 draft by the Panthers, and in his eight years with Carolina he had amassed 81 sacks. Still, his contract demands for several years, and a down season in 2007 during which he recorded only 2.5 made it look probable the Panthers would not try to re-sign him. This despite the fact that teams rarely allow a generationally-great player get away from their team. Rumors began to leak just prior to the free agent signing period that the Bears were surprisingly the top team in pursuit of Peppers. Rumors became reality on the opening morning of free agency when Smith boarded a plane to personally visit and recruit Peppers just hours after he became eligible to sign. And the personal attention paid off when Peppers quickly agreed to a six-year, $91.5 million contract with the Bears.

1. Jay Cutler-QB-Trade 2009: Regarding franchise quarterbacks, defensive ends and left tackles, the old adage is that teams usually can only get one at the very top of the draft, and once they do get one, they never part with him. Thus the NFL world looked on in wonderment in early 2009 when a battle began brewing in Denver between incumbent Pro Bowl quarterback Jay Cutler and new head coach Josh McDaniels. Cutler had caught wind that McDaniels preferred a more conservative signal caller, and tried to engineer a trade that would have sent cutler off in order for the Broncos to acquire Patriot backup quarterback Matt Cassel. Once Cutler learned of the deal that never was, he felt disrespected and vowed that he would not play for McDaniels. The rest of the league and its fans scoffed at the possibility-teams just do NOT trade Pro Bowl quarterbacks, especially those that are only entering their fourth season. Cutler was roundly viewed as sometimes disruptive and not universally well-liked, but he possessed rare skills for a quarterback with his feet and shotgun-strong arm. And despite the fact that he played with a rare disability for an athlete, type-2 diabetes, he was extremely durable, starting all 37 games in which he played from 2006-2008. As weeks of the dispute went on, it became increasingly clear that Denver would indeed entertain trade offers from other teams, which would make the transaction almost unprecedented since the Bears sent Bobby Layne packing in 1949. Even when it was clear, and confirmed by Broncos owner Pat Bowlen that the Broncos were officially going to trade Cutler, most veteran Bears observers thought it would be impossible for the Bears to wind up with the player. While it was true that the Bears had failed to secure a durable franchise quarterback since Sid Luckman in the 1940's, this just wasn't the kind of sweepstakes the Bears organization normally got involved in. Historically speaking, the Bears made cautious moves and focused on building their team carefully over the long run. But on April 2, 2009, late in the afternoon, Bears nation was estatically shocked to learn that Jerry Angelo did indeed pull the trigger on the boldest move of his career when he traded for Cutler. The deal sent Chicago's first and third-round draft picks in 2009, their first-round pick in 2010, and Bears quarterback Kyle Orton to the Broncos for Cutler and Denver's 2009 fifth-round pick. Word had it that the Washington Redskins were also in the Cutler derby, but Denver preferred Orton to Washington's Jason Campbell. So starting in 2009, the Bears had their first young, durable, top-tier NFL quarterback since Luckman. While there are still some, our guess is those not in Chicago, that still don't believe that Cutler is a top-tier quarterback. In 2009 he threw more interceptions than touchdowns with questionable receivers and a leaky defense. In 2010 and 2011 he blossomed (until sidelined by an injury late in 2011), but was still hamstrung by offensive coordinator Mike Martz' schemes. His fans believe that under a more balanced offense in 2012 he will thrive. Regardless, the Cutler trade was Jerry Angelo's top non-draft acquisition in Angelo's tenure with the Bears.

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