first as quarterback of the Denver Broncos from 1983-1998 that include five Super Bowl trips and two titles and again as Head of Football Operations from 2011 to now that saw another two Super Bowl trips and one more title. John Elway has always known winning as a member of the Denver Broncos. Until now...Since Peyton Manning retired Drew Lock Jersey Black , the Broncos have been stuck in quarterback purgatory that Elway has tried in vain to fix. To be fair to him, the pickings were slim. With each passing year, it seems Elway is hesitant to pull the trigger on a big-time, risky move. Instead, playing it more cautious. First, he didn’t have enough star power and finances to compete with the Minnesota Vikings for Kirk Cousins and, instead, landed Case Keenum for $18 million a year. Then, he had a chance to get a quarterback in the 2018 NFL Draft with both Josh Allen and Josh Rosen available, but instead drafted Bradley Chubb. That decision looks smart so far, but he could have been more aggressive to move up ahead of the New York Jets to grab Sam Darnold, who has been much better than the other rookies so far.In 2017, Elway decided not to mortgage their draft future in an attempt to aggressive pursue a quarterback. Patrick Mahomes and Deshaun Watson went 10th and 12th while the Broncos stood firm drafting Garett Bolles who has led the NFL in penalties since coming into the league.In 2016 Steve Atwater Jersey , Elway picked up the scraps left on the table left by the Los Angeles Rams and Philadelphia Eagles who traded up to the 1st and 2nd spot for their franchise quarterbacks. The Eagles won a Super Bowl last year and the Rams look like the best team in football this year. Elway sat back and traded up to beat the Dallas Cowboys to Paxton Lynch. However, Lynch turned out to be one of the biggest busts in NFL history and the Broncos were saddled with Trevor Siemian for two forgotten seasons.The plain and simple fact is that Elway has approached the long-term solution at quarterback with trepidation and risk-aversion. That is now killing Elway and the Broncos as the losses begin to mount. And time is running out for Elway.In fact, 2019 or 2020 will end up being the time for one last Hail Mary from Elway. One that will make or break his legacy in Denver. Nothing can take away from his accomplishments, but failing to recover after Manning’s departure would leave a permanent stain on his years in the front office. In my opinion, he has one task ahead of him for the next two years. Find a quarterback he and his staff is convinced we be the next star in the NFL and go all-in like the Kansas City Chiefs and Houston Texans did in 2017 and the Rams/Eagles in 2016. It may not work out - as they usually don’t - but the time for lollygagging with the most important position in the game has come and gone for Elway.Denver Broncos vs. Chicago Bears: Five things to watch during the Broncos week two preseason matchup Today, the Denver Broncos will host quarterback Mitch Trubisky and the Chicago Bears in week two of the Preseason. Last week, the Broncos first team offense and defenses struggled against the Vikings, but Chad Kelly provided some excitement in the second half. How will things shakeup this Saturday night? I give you five things to watch during tonight’s week two preseason matchup against the Chicago Bears.1: How will the first-team offense and defense rebound?Last week, the first team offense entered the game against the Vikings with a ton of hype. Case Keenum was tossing dimes in practice, rookie Courtland Sutton was making big plays, and the offense in general just seemed much improved from last year. Unfortunately, they had two drives and both times went three and out. Ron Chenoy-USA TODAY SportsNow this week, quarterback Case Keenum had a bounce back week during the joint practices and will look to continue that during tonight’s game.As for the Broncos first-team defense Womens Bradley Chubb Jersey , they also struggled. They struggled against the run and quarterback Kirk Cousins went 4-4 for 42 yards, and a touchdown. The Broncos leaky run defense was a big reason for these struggles, but Head Coach Vance Joseph believes it is something they can correct easily moving forward.This week, they will face the Bears strong rush attack led by Jordan Howard as well as the Bears tight ends who gave the defense some fits during practice this week. They bounced backed nicely during the second day of joint practices so it will be interesting to see how they perform on the field tonight. 2: Chad Kelly with the second-team offenseThe big news around Broncos Country this week was Paxton Lynch being demoted to the third-team and Chad Kelly moving up to the second team offense. Now we will get to see how Kelly performs as tries to prove to the Broncos that he can be their backup quarterback in 2018.Ron Chenoy-USA TODAY SportsHead Coach Vance Joseph told media earlier this week that the expectations for Kelly remain the same as he moves from the third team to the second team. General Manager John Elway also spoke to the media this week and told reporters that he “had a feeling that he(Kelly) was play well”.Kelly threw for two touchdowns last weekend and added a spark to the offense that really was struggling before he entered the game. With Paxton Lynch struggling and being demoted to the third-team(and potentially off the roster) Kelly has a good chance to become the Broncos new developmental young quarterback on the roster. He also has a chance to prove to Elway and Vance Joseph that he can be trusted to be their backup quarterback behind starter Case Keenum. So how Kelly performs, good or bad, will likely be a big topic at the end of this game. 3: Can Isaac Yiadom nail down the third cornerback job?Last week, we saw Yiadom on the wrong end of some big plays against the Vikings. He was manned up against Stefon Diggs a few times which is a tough matchup for any cornerback in the NFL, especially a rookie playing in his first NFL game. In the end, he gave up a touchdown while covering Diggs during the Vikings first series last weekend. The silver lining for Yiadom is that he was in good position for a lot of these plays and wasn’t beat badly by any means, It shows that he knows what he is doing out there and reading/reacting well. Not bad for a rookie corner making his first NFL appearance.Head Coach Vance Joseph echoed these thoughts when asked about Yiadom after the game.Against the Bears, we may see Yiadom start or get some valuable playing time with the first-team offense with cornerback Chris Harris Jr. likely sitting out this game. This will give Yiadom a chance to improve on his decent showing week one and try to lock down the number three corner job. Veteran Tramaine Brock will likely play as well so it will be a big game for the Broncos third-round pick in this years NFL Draft. 4. Royce Freeman the starting running back?Rookie running back Royce Freeman put up the Broncos first offensive points in 2018 as he scored a 23-yard rushing touchdown against the Vikings last week. After the game, Quarterback Case Keenum was asked about Freeman and he praised the rookies pass blocking ability. Pass blocking is usually where rookie backs struggle and why they do not see the field, so it is promising the see he is excelling in this area early on. Add that to his running ability Womens John Elway Jersey , and Freeman could be on the brink of a breakout season for the Broncos. Photo by Dustin Bradford/Getty ImagesThen earlier this week, Head Coach Vance Joseph dropped a nugget that could point to Freeman likely being the Broncos starting running back. He was asked about the difference between veteran Devontae Booker and rookie Royce Freeman. He called Booker a “third-down back” with good pass-catching ability while calling Freeman the “one cut, downhill pounder with good vertical speed”. To me at least, Joseph pretty much named Freeman the starter right here without officially saying it. You don’t call your starting running back a third-down guy while praising a rookie back with bell-cow running back traits. If Freeman comes out and gets plenty of reps with the first-team offense and plays well, I think this running back competition will be all but settled. 5. Looking for a rebound from rookie Bradley ChubbEntering the game. I had high hopes for the Broncos fifth overall pick thinking he would wreck the Vikings second-team offensive line. However, he ended up having a tough night and was responsible for a few big run plays. He also didn’t record any sacks. Maybe it was rookie jitters, maybe the defense in general just played sloppily, or maybe it was a combination of both. Either way, it wasn’t a great showing for the Broncos fifth overall pick. However, I think he will bounce back in a big way tonight against the Bears.Chubb has been having a great camp and was bringing the heat during the joint practices this week. General Manager John Elway was asked about Chubb, and he had some high praise for the Broncos first-round selection. Chubb figures to get the start opposite of Von MIller once again tonight and will look to make life a living hell for Bears quarterback Mitchell Trubisky.