It's hard to wrap your brain around how some teams could be so bad for so long. Talent moves with such fluidity from team to team in the NFL that it seems to defy probability when a team sets up residence in the cellar.
Two criteria inevitably have to have been met for these teams: extreme amounts of whiffing on draft picks; and severe quarterback struggles.
It's always easy to point and laugh in retrospect. This may not be a popular opinion, but you need a pretty decent amount of luck given how much of a crap shoot drafting can be. There's always been consensus "can't miss" prospects that are complete busts, the same way there are late round or undrafted superstars. Even if these teams were lead by blind squirrels sniffing around for the mother lode, you'd expect they might happen upon some high quality quarterbacks somewhere along the way.
Another real problem for struggling teams is continuity. Coaches and general managers are shown the door at such an alarming speed, and the team design usually is blown up with it. Because of this, the team becomes less of an attractive destination for top quality free agents, and inevitably some drafts become a series panicky reaches in an attempt to save front office jobs.
The majority of successful NFL teams are built the same way: methodical acquisition (and retention) of talent, mostly through the draft. Free agency is only used to fill a few glaring needs, which keeps costs down to avoid salary cap struggles.
Glancing at the list, I think one, maybe two teams out of these ten actually came close to that model. The rest were more of a panicky mess than the result of an obsessive compulsive person with a huge pile of multi-colored Legos on their bed.
10 Cincinnati Bengals: 102-121-1 this Millennium
I suppose I'm not that shocked the Bengals floundered their way to #10 on this list. Despite bursting with talent the past few years, the Bengals of the 2000s mostly have been a ship with a permanently drunk navigator. Carson Palmer's play was confusingly unpredictable, including his play off the field with the weird fake retirement after 2010. Premiere pass catchers like Terrell Owens and Chad Ochocinco-Johnson-Whatever somehow managed to detract from their evident talent with unprecedented fits of diva. Seriously, despite their skills, I would have a permanent welt in my forehead from all the facepalming I'd do if I were a Bengals fan in 2010. I have fine news for Bengals fans who have had to watch this confusing franchise for the past decade and a half: you are undoubtedly one good (doesn't even need to be great) quarterback away from being a serious Super Bowl contender. Win rate over this time period: .455.
9 Kansas City Chiefs: 100-124 this Millennium
Here's a list of a few awe-inspiring names that graced the QB position for the Chiefs since 2000: Elvis Grbac, Brodie Coyle, Damon Huard, Tyler Palko, Brady Quinn. Other than Trent Green from 01-05, and a few moments of success Matt Cassel has had, the position has been beyond woeful. Of course, that has all changed now with the efficient workmanship of Alex Smith, probably one of the more underrated starting QBs in the NFL. Fun fact: the Chiefs scored more points (430) in 2013 than they did in 2012 and 2011 combined (423). At least for most of the 2000s chiefs fans enjoyed watching Tony Gonzalez make defenders look dumb on a game-to-game basis. Much like the Bengals, this team is also rife with talent now, and ascending to power quickly. I expect they probably wouldn't be on this list if it were to be re-written in 2020. Win rate over this time period: .446.
8 Jacksonville Jaguars: 95-129 this Millennium
Three. That's the number of winning seasons the Jaguars have had since 2000. Despite being pretty strong defensively for most of the years post-millennium, the offense has been largely abysmal despite some admirable QB work from David Garrard and powerful running from Maurice Jones-Drew. Unfortunately, drafting at the QB position just hasn't gone well. First round choice Blaine Gabbert has been a bust from day one. Gabbert is flinchy, a scattershot passer, and as intimidating as a cactus. Well, let's be fair to the cactus, as it can be a little dangerous if you trip and fall on it or something. It's hard not to feel for workhorse players on the team like Paul Posluszny, who would be hailed as the monster linebacker he is if he played for any other team. I only have one piece of advice for the Jags moving forward: draft whichever top QB you think is best this year (I'd choose Bortles) and pray he lives up to the billing. Until quarterback play improves, the franchise is just floating around in oblivion. Win rate over this time period: .424.
7 St. Louis Rams: 94-129-1 this Millennium
Yep, the Rams just barely edged out the Jaguars for the honor of 7th worst team by managing to tie division rival 49ers in week 10 of the 2012 season. It's worth noting that despite the just miserable record the Rams had from 2004 on, they started the millennium having just won a Super Bowl with the resurgent Kurt Warner and 'the greatest show on turf'. In 2001 they would play in the Super Bowl again behind the incredible play of Warner and RB Marshall Faulk, but they lost and Warner moved on from the team. Fans would then be subject to years of mediocrity in QB Marc Bulger, before Sam Bradford was drafted 1st overall. Despite that, they have yet to have a winning season with Bradford under center. In fact, they have only had one winning season since Warner retired. I wish I could say I was optimistic about the Rams moving forward; but given the lukewarm production and health issues of Bradford, and the incredible competition in the NFC West, I'm not sure they have much of a chance unless they really hit it big with the glut of draft picks they've accumulated. Win rate over this time period: .420.
6 Washington Redskins: 94-130 this Millennium
Tight race from 8th to 6th, the Redskins managing to trump the Rams as the 6th worst team by digging deep and pulling out one extra loss. Let's take another glimpse into quarterback grandeur with a list of some of the QBs who played for the 'skins since 2000: Jeff George, Tony Banks, Danny Wuerffel (sounds like how you'd say waffle through a mouthful of waffles), Patrick Ramsey, John Beck, and Rex Grossman. Bask in the radiant glory. At least now they have two QBs with some potential in Robert Griffin III and Kirk Cousins. And for all those who want to trade Cousins, I think it's worth keeping him on the off chance RGIII ends up a bust. It's a cheap insurance policy, as is. Part of me thinks the team would be better off if rather than paying such a steep price in draft picks for RGIII, they had just picked value, kept their picks and selected Kirk Cousins as they had, letting him start. I suppose I'll file that away under hypothetical strategies if I somehow Frank Underwood the entire NFL and become a General Manager somehow. Win rate over this time period: .420
5 Arizona Cardinals: 90-134 this Millennium
Yet another benefactor of the unlikely hero, Kurt Warner, who took them to the Super Bowl in 2008, though they lost to the Steelers. Except for 2008-2009 with Warner under center, the Cardinals only had one winning season since 2000: last year, where they went 10-6 but missed the playoffs because of an incredibly strong NFC. If 2013 is any indication, they now are a well balanced, defensively underrated team that could really continue to be relevant even in the talent-ridden NFC. Basically, the entire rest of the decade-and-a-half are times to be forgotten. This recent resurgence is really the least the Cardinals can do for superstar wideout Larry Fitzgerald who has blessed Arizona with his workmanlike attitude and unreal talent as they trolled through the muck. All you fine folks in the sun-blasted desert can smile when football season comes around again, because it would appear the dark days are behind you, for now. Win rate over this time period: .402.
4 Buffalo Bills: 88-136 this Millennium
I can hardly believe this is true, but the Buffalo Bills have only had 1 winning season since 2000. That season was 2004, where they went 9-7 with Drew Bledsoe under center and Willis McGahee at tailback (though it was defense that really shined that year). They are also the only team on this list never to have made the playoffs since 2000. Jeez, that is demoralizing. Their future regarding breaking that streak will be directly connected to how 2013 first round draft pick EJ Manuel fares moving forward. If he doesn't pan out it could set the franchise back a number of years. Furthermore, I would rather have spent money on keeping drafted talent like safety Jairus Byrd than breaking the bank on turbo-expensive free agents like Mario Williams. Some optimism was generated in recent years with the sometimes scintillating passing of Harvard graduate Ryan Fitzpatrick, but the bearded wonder never brought them to a record better than 6-10. Win rate over this time period: .393.
3 Oakland Raiders: 86-138 this Millennium
The turn of the millennium was a magical time for the Raiders. It unfortunately was short lived. Mostly under Coach Jon Gruden, the Raiders were 33-15 from 2000-2002. They went to one Super Bowl, and were robbed of another because of the infamous 'tuck rule' game vs. the Patriots. The fall thereafter was precipitous. From 2003 to today they do not have a winning season, and were thrown into utter disarray after the catastrophic saga of one of the most decried #1 draft picks of all time, JaMarcus Russell. Russell was one of the most highly touted college prospects of the decade, but for the Raiders he lacked any motivation, grew overweight and became addicted to codeine-laced drinks or 'sizzurp'. In the 2010 offseason he reported to camp weighing over 300 lbs. He was cut before the season started. This landmark catastrophe in NFL history is clearly one of the prominent reasons the Raiders have been living in the swampy bottom of the NFL. At least now, the monstrous amount of dead money that has been hovering over the team for years is finally gone, and they can truly begin to rebuild in 2014. Perhaps a bit of prudence in your decision making will be in order moving forward, Raiders. Win rate over this time period: .384.
2 Cleveland Browns: 75-149 this Millennium
Nineteen is the number of starting Quarterbacks the Browns have had since 2000. Well, at least they haven't been idle in trying people out at the position. There isn't really much else of a reason as to why they've been so awful other than that. They've had some talent sprinkled in there, especially lately with Joe Thomas, Joe Haden and Josh Gordon, who are top players at their position in the NFL. A lack of consistency in coaching and front office has also been a systematic problem. Patience has not been in large supply, since they've only been to the playoffs once since 2000, and have only had 2 winning seasons. Panicky draft picks like Brandon Weeden (who wants to draft a 28-year-old?) and trading up one spot for some reason to pick Trent Richardson are clear indications of a mismanaged franchise. Tom Heckert, the acting GM of that time should never be allowed to just throw away a year of draft talent by basically gambling to save his job. At least they were able to get some value back trading Richardson to the Colts in 2013. While QB Brian Hoyer showed some promise and might be the future for the position, the team's draft choices this year are going to have a huge impact on how the team performs in the future; there are some key pieces in their prime right now who you don't want to go to waste as the team languishes. Good luck on draft day. Win rate over this time period: .335.
1 Detroit Lions: 69-155 this Millennium
To those NFL fans who joined our ranks recently and don't have a burning desire to plumb football history, this might be a shock. The Lions have averaged 4.9 wins per season since 2000. How is this so? Well if you don't know the name Matt Millen, then let me elaborate. Matt Millen won four Super Bowls with three different teams as a player; but unfortunately, good players do not necessarily make good General Managers. From 2001 to 2007 Matt Millen against all odds held the GM job, perennially making head-scratching draft picks and failing to construct a complete team, picking a wide receiver with his first pick in four of his seven drafts. The team had terrible line play and nothing but stopgaps and question marks at quarterback. His last year before he was fired, Millen picked Calvin Johnson 2nd overall in 2007. It was one of the only good draft picks he made in seven years. He was later said to have "made more bad draft decisions than anyone else in two centuries." And Millen himself said publicly his leadership had been "beyond awful." A great player and a kindly man, Millen unfortunately drove the franchise into the ground. At least Calvin Johnson has grown into the best receiver in the entire NFL, and with a dominant defensive line and a gunslinger in Matthew Stafford, this team really can be something special with the right coaching. Win rate over this time period: .308.