The story goes that during the bye week of the 2007 NFL playoffs, it was Jessica Simpson’s father, Joe, who tipped off US Weekly magazine that his daughter and the quarterback of the Cowboys would be hitting the Mexican beach resort destination.
“I’ll be honest — I had never heard that,” said former Cowboys linebacker Bobby Carpenter, who along with offensive lineman Marc Colombo and tight end Jason Witten enjoyed the quick trip to Mexico with Romo. “This was before Twitter. People took some pictures of Jess — they knew who she was. I never thought about how bad this would look for Tony.”
Six days later after returning from Mexico, the top-seeded Cowboys lost at home to the New York Giants in the divisional round. The “trip to Cabo” was partly blamed and became a defining moment in Romo’s career.
The moral of the story for his successor? Don’t go to Cabo. The trip had nothing to do with the Cowboys’ loss to the Giants, but it’s a bad look and it’s not worth it.
The “trip to Cabo” remains the single most exaggerated story in Romo’s hyperbole-filled tenure with the Cowboys; it was a nothing but was a bad look that his successor has no plans to follow. When I asked Dak Prescott if he was going to get out of town during this bye week, he said he will be hanging out watching football.
“Nice try,” he said with a smile.
The last time the Cowboys had a playoff bye was ’07, when they finished as NFC’s top seed with a 13-3 record. Romo was in the midst of a relationship with hot blonde/pop star Jessica Simpson.
Wade Phillips, in his first year as the Cowboys coach, had no authority, or intention, to tell his team to stay in DFW during the bye week.
Romo’s previous coach, Bill Parcells, had no authority, either. But he would have gone out of his way to make it difficult for players to go anywhere; he would have had a late Friday meeting, or practice. Or he would have kept the Friday schedule a secret until the last minute, to make it difficult for players to make plans.
Unlike Bill, who treated his players like teens he did not trust, Wade let them do as they desired.
Romo and his buddies would never have fathomed to flee to Cabo had Parcells been the head coach.
But Wade was the coach, so Romo and a few of his closest friends on the team went to Cabo — a 2 1/2 -hour flight from DFW.
“We only left the house one time,” Carpenter said. “We went on a boat tour of the arches there, but other than that we were inside the whole time. We had a chef who was there and we were in bed every night by 10:30.
“I did less there than had I stayed back at home in Dallas.”
In the week leading up to the game, Phillips blew off the trip to the media as not a big deal. He did offer the foreshadowing that it would only be a big deal if they lost.
“I really never thought too much about it,” Carpenter said. “Tony doesn’t worry about that kind of stuff, and if he doesn’t worry about it, then I’m not going to worry about it.”
The Cowboys went out and dogged it up in a 21-17 upset loss to the Giants; Romo was 18-of-36 passing for 201 yards with a touchdown. In the final minute, the Cowboys reached the Giants’ 23-yard line, but Romo’s fourth-down pass was intercepted in the end zone with nine seconds remaining.
The day after the loss, Phillps was asked by the media if the trip to Cabo was a distraction; of course, Wade said it wasn’t and added he knew just such a conclusion would be drawn.
Pre-playoff vacationing is back in the news after New York Giants receivers Odell Beckham Jr, Victor Cruz and Sterling Shepard were seen partying in Miami the day after a season-finale win.
“They weren’t even on the bye week like we were,” Carpenter said. “If you win, it’s a non-issue. If you lose, it’s a big deal.”
The Trip to Cabo has followed Romo ever since; it was just an example of the Hollywood elements that No. 9 enjoyed as the starter. The trip also embodied Wade’s often nonchalant attitude toward nearly everything.
Tony’s trip was not the reason the Cowboys lost against the New York Giants; the Giants were rolling toward a Super Bowl, and the Cowboys had lost their edge in the final four weeks of the season; Wade did not have it in him to keep a group engaged on the necessary level when distractions abound.
Given the difficult nature of the NFC, there is a good chance these top-seeded Cowboys will again lose in the divisional round.
The difference is this time a trip to Cabo won’t be used as an excuse.
Listen to Mac Engel every Tuesday and Thursday on Shan & RJ from 5:30-10 a.m. on 105.3 The Fan.