For the last two seasons I have done a summer “Best and Worst” contracts for each team in the NFL, but I decided this year to put that on hold since it recycles so many players and instead take a positional approach to the concept. So during the course of the summer I’ll do my choices for the top three and bottom three contracts at each position from a team perspective. As usual the rules are no rookie contracts allowed in the selection.

Today I’ll give my opinion on the worst contracts at the quarterback position. That doesnt mean worst player, just the deals I felt teams may have most compromised themselves on the structure or stuck their head out most on the valuation of the contract.

3. Cam Newton, Carolina Panthers (5 years, $103.8 million, $41 million fully guaranteed)

There were a few players I considered for this spot. Drew Brees’ contract was horribly structured, but is a terrific player. Ben Roethlisberger’s new contract is incredibly player friendly, but he is also the catalyst for the Steelers. Carson Palmer’s contract pushes a lot of money into the future. But when I factored in the structure, contract size, body of work, and timing of the contract I thought Newton’s new contract surpassed them all.

Newton’s contract is based on the theory that the strength of being a top draft pick still outweighs some of the lack of production of the player. Newton set the NFL on fire as a rookie, but his numbers have dropped and in 2014 hit career lows in passing yards (3,127) and touchdowns (18). His rushing efficiency has declined and given the usual career path of the QB you never want to pay for that anyway. While he has not had a good supporting cast around him, it’s still a leap of faith to assume that’s the only issue.

That leads me to the odd timing of the contract. Given the huge contract and top end cash flow metrics, this is nothing Newton could have done in 2014 that he did not do in 2013 to warrant the extension. He didn’t play better. The team didn’t improve. He didn’t win a Super Bowl. If you know you are going to extend the player on his terms do it earlier to improve the cap structure and guarantee structure of the contract. The Panthers should have been able to mitigate the risks in the contract by signing him prior to the start of the 2014 season rather than 2015.

The result was a contract structure that is tremendous for Newton. $32.5 million in prorated money over a two year period is a great win for a player. There is no season in which Newton is under contract where there is $0 in dead money and in his second to last year there is still $8.5 million sunk. He is the top earning quarterback to never win a Super Bowl and of the top nine at the position, one of only two (Ryan Tannehill is the other) to not reach a championship game prior to signing.

The contract runs almost identical to Matt Ryan’s, another super friendly player contract, but to compare Ryan to Newton is putting all the negatives of Newton solely on the supporting cast on offense around him. Any way you spin it, Newton’s contract will be one that any high pedigree, limited performance player will try to use to increase their value in their upcoming contract negotiations.

2. Jay Cutler (6 years, $126 million, $38 million fully guaranteed)

This was one of the strangest contract decisions of recent times. The Bears allowed Cutler to play out his contract seemingly because there was a disparity in valuation. That seemed somewhat logical since Cutler was looking for what was considered top starter money and anyone should have had reservations about making Cutler that player. After all what were the benefits of Cutler? He was drafted highly in 2006? He has a rocket arm which he loves to tell you about?

Statistically Cutler hasn’t been a top tier guy since 2008 when he threw for 4,500 yards and was then traded to Chicago. In the interim five years passed in which Cutler averaged under 3,000 passing yards per year on about 60% passing with a 20/15 TD to interception ratio. I’m not sure what you call that, but I am sure you don’t call it a top line starter. There were no intangible qualities either. Reportedly teammates don’t care for him. Coaches didn’t necessarily like him. He wasn’t a prolific winner. He was just a guy that had a gifted arm and one good season.

The Bears should have had every benefit when negotiating a contract with Cutler after the 2013 season. Cutler had been hurt again and missed five games. That left him with just 2,600 yards on the season and his fill in, Josh McCown, lit up some bad teams filling in. But Chicago acted as if there was no leverage and rewarded Cutler with a massive contract that essentially would guarantee him $54 million.

When I mention the timing of the Newton contract, this one is 100 times worse. Chicago had so many opportunities to extend Cutler before he was about to hit free agency. In 2012 Cutler went 10-5, 3,000 yards, 19/14 TD/INT. In 2013 he went 5-6, 2,621, 19/12. What made this 2013 so much better that they went from “cant extend at this price” to “whatever you want we’ll sign it” is a question nobody can answer. That logic got the general manger fired.

Rather than building in old money into Cutler’s guarantee package the $54 million is entirely made up of new money. With most of the guarantee being earned by March of 2015, that made this arguably one of the worst guarantee structures in the NFL for any team. It was touted as a benefit for the team that no signing bonus was included (they had to quickly restructure and add one in a few weeks later) but with the monstrous guarantee it more or less provided a block to movement the same as a bonus. Other teams were soon able to do contracts with better guarantee structures and cash terms for similar question mark players but Chicago didn’t even seem to try to go down that path. Had they signed Cutler in 2013 rather than 2014 they would have been able to release him after this year and probably saved themselves around $10 million. Instead they are more or less stuck with two more seasons of likely lackluster play and sulking on the sideline while they keep their fingers crossed that he can justify the contract. Out of all the big QB contracts in the NFL this one probably has the least upside at time of signing than any other player.

1. Joe Flacco, Baltimore Ravens (6 years, $120.6 million, $29 million fully guaranteed)

Every star in the universe aligned for Flacco when he earned this massive haul following his 2012 Super Bowl championship, making him the highest paid player in the NFL at the time of signing. Prior to his Super Bowl win Flacco was probably looked at as a $15-17 million a year player, not that far off from an Andy Dalton type. He’s a 3,600-3,900 yard a year type passer with a very strong arm in a league where players are chasing 5,000 yards. But his playoff record has been good and his 11 touchdown/0 interception run in 2012 is as good as anyone’s in history.

Flacco was probably the first test case of a non top half of the draft player earning a massive contract because of a playoff run. While Ben Roethlisberger and Eli Manning accomplished similar feats they were picked 11th and 1st overall and, I believe, at the time considered higher upside players. It’s the Flacco contract that helped paved the way for a Colin Kaepernick to receive $19 million a year with $12 million in upside potential for having a team run like the Ravens did.

What makes the contract stand out the most though is the structure. In order to fit Flacco in their salary cap, the Ravens used a series of prorated bonuses totaling a whopping $51 million and then backloaded the contract. This leads to a showdown in 2016 where Flacco’s cap charge is $28.55 million but the cost to release him is $25.8 million. It gets worse from there with a $31.15 million cap number in 2017 and the sunk cost is still over $15 million. This is similar to the monster that was the backend of the Ndamukong Suh contract with the Lions in which there is no leverage to really push for an extension.

Normally when teams stick their neck out on a market pusher they know that the tail end of the contract will be beneficial if salaries continue to rise or the player fails to perform and needs to be released. The Roethlisberger, Manning and Philip Rivers contracts all were big market deals but eventually ended up being normal because of the change in the landscape. The Ravens will never get that with Flacco because the backend of his deal outpaces the market. It is hard to imagine any recourse other than extending Flacco. Given the landscape of the market and incredible leverage Flacco has it would not be surprising to see him get a new deal worth over $23 million a season next year even if it’s another season of less than 4,000 yards in the air, especially if Russell Wilson ends up the highest paid player in the NFL. While Flacco will never give you the dowside of a Cutler, this deal has the makings of one of the great player contracts of all time.