Condon, 59, is arguably the NFL’s most powerful agent, evidenced by his A-list of clients. Peyton and Eli Manning. Drew Brees. Tony Romo. Matthew Stafford. Matt Ryan.

While Eli will lead the New York Giants into the Super Bowl, Peyton’s status as the face of the Indianapolis Colts is in limbo. Brees’ contract with the New Orleans Saints just expired. And Alex Smith, who revived his career with the San Francisco 49ers, needs a new contract, too.

MORE: ‘Politician’ Manning responds to Irsay

It is shaping up as another eventful offseason for Condon, but that was hardly a source of anxiety as he unwound after the NFC title game.
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He was pondering a whirlwind schedule. After San Francisco, Condon, who heads the football division of Creative Artists Agency (CAA), flew to Bradenton, Fla., to check on rookie clients prepping for the league’s scouting combine.

Last week, he made a similar trip to Phoenix. A mid-week stopover at his base in St. Louis was followed by a haul to Honolulu for the Pro Bowl, where he’ll get face time this weekend with their 17 clients in the game.

Next week, Indianapolis.
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“This time of year, it gets to be a bit of a crowded schedule, but it’s not too tough,” says Condon, who played guard for 12 NFL seasons during the 1970s and ’80s. “A tough schedule is two-a-days with live pads.”

As the lounge emptied, a New York writer stopped at the table and asked Condon about the chances that Peyton Manning could end up with the Jets.

Condon shrugged. He has been peppered with such questions for weeks and says it comes with the territory.

But he still can’t fathom what drove actor Rob Lowe to tweet last week that Manning was retiring. “Very unusual, considering that Peyton doesn’t know him,” he says.

Manning, rehabbing from his third neck surgery in 19 months, was paid $26.4 million this season despite not playing a down after signing a five-year, $90 million contract in July. Yet with a $28 million roster bonus due March 8, conditions are ripe for the Colts — cleaning house in firing President Bill Polian and coach Jim Caldwell and poised to draft Stanford quarterback Andrew Luck with the No. 1 pick overall — to cut Manning.

“I’m not in a very good place for healing,” Manning told The Indianapolis Star this week, and Colts owner Jim Irsay shot back Thursday that he preferred that the quarterback kept such comments “in the family.” That Irsay labeled Manning a “politician” adds another layer to speculation about where he could wind up. Jets? Arizona Cardinals? Washington Redskins?

“Peyton is under contract,” Condon says. “If that changes, we’ll consider the options.”

Even amid the league’s what-have-you-done-lately culture, the prospect that the only four-time NFL MVP could so suddenly become an unrestricted free agent is astonishing. Irsay contends the decision on Manning will be strictly medical. Manning could agree to push back the date he is due the bonus, but that has not been expressed.

“The deal that Peyton signed in August was very leveraged, a strong deal for Manning,” says Andrew Brandt, a former NFL front office executive who analyzes business issues for ESPN and Manning’s deal is structured to pay $72 million during the first three years — provided the Colts don’t terminate it.

“And to have two of the most prominent quarterbacks in the league in these situations, it’s very rare,” Brandt added.

The other case Brandt alluded to involves Brees, who set the NFL’s single-season passing yardage record in December and might be on the verge of setting a record on the contract front, if his next agreement exceeds deals for Manning and New England Patriots quarterback Tom Brady that average $18 million.

Brees broke off talks during the season, citing the potential of a distraction, but negotiations are expected to resume soon. The Saints can prevent Brees from becoming a free agent by using their franchise tag on him, but with other key players due for deals, that is a last resort.

“It was curious that they let the contract run out,” Brandt said. “When I was in Green Bay, we were never going to let Brett Favre get to the last year of his contract, or even the last two years, without getting a new deal in place.”

Last week, Brees said he agreed with coach Sean Payton’s assertion that he would be “beyond stunned” if Brees was not with the Saints next season.

“I’d probably be out of a job if he wasn’t, right?” Saints general manager Mickey Loomis told news reporters this week at the Senior Bowl in Mobile, Ala. “I think it’ll work out.”

Says Condon, “There was obviously a difference of opinion. But the circumstances continue to change. He played through this last year. Now it’s a different set of circumstances.”

Smith, drafted No. 1 overall in 2005, might not hit the free agent market, either. Last week, 49ers CEO Jed York indicated that he wants to retain Smith on a long-term basis.

“It’s a two-way street,” York said. “I hope he wants to stay here.”

Says Condon, “Each of these situations is unique.”

Time for second career

That Condon — whose five biggest contracts negotiated totaled $438 million — has evolved into the agent for so many marquee quarterbacks is a bit ironic. As a player, Condon was not among the elite and was never voted to the Pro Bowl. Drafted in the 10th round from Boston College in 1974, he started 131 of 148 games during 11 seasons with the Kansas City Chiefs and one with the New England Patriots.

The son of Ansonia, Conn.-based lawyer Thomas Condon Sr., Condon began thinking of a second career after injuring a knee in his second pro season.

“My father told me, ‘Son, this football looks like a tough deal. I think you’d better go back to school.’ ”

He took the advice and went to law school during NFL offseasons, and wistfully recalls then-Chiefs coach Marv Levy giving him two days off during training camp to take the bar exam.

“I figured that regardless of what else happened, I’d always have a job with my dad,” Condon says. “I was hedging my bets.”

He went on to serve as the Chiefs’ player representative and then became the NFL Players Association’s president. After retiring from football, he served as outside counsel for the NFLPA and eventually represented union chief Gene Upshaw.

In 1988, he landed his first player client: Chiefs defensive end Art Still.

This practice continues to grow with CAA, the Hollywood talent agency that has become a conglomerate in the pro sports industry with a client list in non-football sports that includes stars LeBron James, Sidney Crosby and Ryan Howard.

Condon and partner Ben Dogra joined CAA in 2006, and recently extended their deal. In November, Memphis-based agent Jimmy Sexton came aboard. Sexton has quarterbacks, too, including Philip Rivers and Tim Tebow, but also represents top coaches such as Nick Saban and Rex Ryan.

Including Sexton’s client base, CAA Football boasts about 150 NFL players, including 14 starting quarterbacks. In the past three drafts, CAA has represented 25 first-round picks — more than any other agency.

While the firm’s clout is well established, Dogra says it benefits from diverse perspectives.

He laughs when comparing, for instance, his negotiating style with Condon’s. “Tom has a longstanding reputation as a tough negotiator,” Dogra says. “Maybe that goes back to his days as an offensive lineman. My strategy is a little friendlier.”

Condon downplays the level of acrimony that can flow out of negotiations. “Neither side wants to hold a grudge,” he says. “There’s only 32 teams, but at the same time we’re an institutional supplier of talent. We have to deal with them again and they have to deal with us.”

Condon doesn’t deny having a fractured relationship with San Diego Chargers general manager A.J. Smith that stems from Eli Manning’s entry into the NFL in 2004. With the Chargers holding the draft’s first pick, Condon, expressing Manning’s wishes, told the Chargers that Manning would not play for the franchise — which drafted him anyway, then traded him to the Giants for Rivers and draft picks (third round in 2004, first- and fifth-round picks in 2005).

“My job, basically, was to explain that he had the option of not playing,” Condon says. “There are few players who are going to be in the position where they could exercise that option. It seemed like that was the best option.”

Since then, Condon has represented several key Chargers But he negotiated through executive vice president Ed McGuire rather than Smith.

When contacted this week, Smith declined to comment.

Griffin in the fold, not Luck

Condon didn’t land Luck, the quarterback projected to be the No. 1 pick in the 2012 draft. That’s notable when considering that CAA has represented six of the past eight players taken in the top slot, but also because of the potentially awkward scenario of Luck’s arrival influencing the Colts’ decision on Manning — or the team carrying both quarterbacks during a transition period.

There is quite an alternative, however. Dogra signed Robert Griffin III, Baylor’s Heisman Trophy-winning quarterback.

“Great on the field,” Condon says. “So much potential off the field.”

What Griffin — or Luck — won’t get is a rookie deal like the one Condon negotiated two years ago for St. Louis Rams quarterback Sam Bradford, which guaranteed a record $50 million as part of a six-year, $78 million contract.

The 10-year labor deal struck last summer includes a rookie salary cap that limited last year’s top pick, Carolina Panthers quarterback Cam Newton, to a guaranteed $22 million.

Under the new labor deal, money previously committed to rookies is funneled to veterans.

“I don’t think there’s anybody on my side of the table that’s excited about the rookie system,” Condon says. “But the deal has guaranteed spending levels, players get 55% of the TV money, and there will be more revenue.”

There are new marks in sight. And much unfinished business.

“Last offseason, we had a lot of free agents to handle in a short period of time,” Condon says of the post-lockout crush. “We’ve got almost two months before free agency starts. … The reality is that we’ve got plenty of time.”

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