It was at the old Texas Stadium when, on his way out of the locker room after a meaningless preseason game in 2006, Tony Romo told me, Were going to win here.To his credit, he was not specific about what he would win.Now we know its the lottery.Thus far, Tony Romos football career may be full of odd and unfortunate timing on the field, but financial wizardry off of it. Romos professional football legacy can partly be defined by the staggering amount of money he has been paid against results that dont quite merit the sum.Figuring that he will turn 33 soon, he has about three or four years to change the perception that his greatest contribution in football will be to his own bank account.A few days have passed and it still hasnt sunk in Tony Romo signed for more guaranteed money in the history of the NFL than anyone but Tom Brady.As the late NBA Hall of Fame coach Chuck Daly once said, Its not about what youre worth. Its about what you can get.Do not blame Romo. He put himself in the position to cash in, and any one of us would do the same thing.If you are going to blame anyone it must be to the man who issued the check Jerry.The deal for Romo makes sense in that it provides some immediate cap relief and secures the services of a solid NFL quarterback.Romos six-year, $108 million contract that includes $55 mil in bonuses directly counters what Jerry Jones has been floating in recent weeks: Romo has been lobbying him that he will do whatever necessary to add help. Maybe he has, but this type of contract is going to put the Cowboys against the cap for a while.Just when it seemed that Jerry had some potential incentive-fueled leverage on Romo to have the year of his life in a contract season, he showers him with a giant guaranteed deal that should allow the quarterback to buy a house in the same vicinity as Tom and Gisele.Say whatever you want about Romo as a quarterback, his timing with the Dallas Cowboys as a professional has been exceptionally lucrative.Look at this timeline of events:• In May 2003, Romo signs with the Cowboys as an undrafted free agent for a signing bonus of $10,000. He turned down a $20,000 offer from the Broncos.• In the fall of 2004, Romo was on a depth chart that featured Quincy Carter, Vinny Testaverde and Drew Henson. Is Romo still on the team if Carter isnt cut during training camp?• In early September 2007, the Cowboys were still trying to determine whether to commit to Romo with long-term dollars or wait out the season to see how things develop.If they committed too early, Romo was going to potentially sign for less money, but the Cowboys had a smaller figure if he didnt pan out.When the Cowboys started 5-0, they knew they had their guy and, a few weeks later, he signed a six-year, $67.5 million deal.The Cowboys finished the season 13-3, Romo went to Cabo, the Cowboys won a bye-week playoff game and the following week were upset at home by the New York Giants in the divisional round.Now here we are in 2013, and Tony Romo has one impressive wild-card win against the Phiadelphia Eagles in 2009.He has steadily improved, and a case can be made no team asks more from its quarterback than Romo. He plays hurt. He wants to play all the time. He has good numbers, and he has had his share of impressive moments and wins.His line has been erratic to bad, his receiving corps ranging from good to great to average.There is always some reason, but in the end, Romos career record as a starting QB is 55-38. Pretty good. His career playoff record is 1-3. Putrid.Is it worthy of a contract that is either the same, or more than, the likes of Drew Brees, Brady or Joe Flacco?No.This is not about fair, or worthy. This is about what you can get. Romo got it, and good for him.Despite what you may think, the man cares tremendously about playing well, and winning.If, however, he wants to change his legacy, he just needs to win something other than the lottery.
Mac Engel, 817-390-7697 Twitter: @macengelprof