Q&A: Longtime NFL agent Leigh Steinberg talks Patriots’ winning ways, representing Drew Bledsoe

This Patriots offseason, more than any other perhaps, has fans questioning if Bill Belichick and his staff can still craft a winner after two decades with the greatest quarterback of all time.

But despite the losses of several key players, including All-Pro cornerback J.C. Jackson and starting right guard Shaq Mason, New England keeps on reloading, adding versatile, experienced defenders like Malcolm Butler and Jabrill Peppers and trading for big receiver DeVante Parker to aid young quarterback Mac Jones.

One veteran NFL agent says Belichick’s keen eye for value, along with his fearlessness in making difficult roster decisions (including one with a well-known client of his), is what has made the Patriots the best franchise in NFL history.

Boston.com spoke with Leigh Steinberg, an NFL agent of 48 years and CEO and chairman of Steinberg Sports, about what makes the Patriots and their enigmatic leader tick and what’s kept them at the top of the NFL for two decades.

After all these years watching the Patriots or working with players who played for them, what’s the biggest takeaway you’ve had about how New England does business?

Well, part of why they keep winning is the modularity of players. Belichick has a keen sense of when a player’s outlasted his utility, when a player’s not a good bet for a long-term contract, when a player is not critical to them winning. And so they’re able to not re-sign players that are not critical, based on his rankings. They’ve never had the most Pro Bowl players. They don’t have the most superstars, and yet they win anyway because of their system.

They have a terrific owner [Robert Kraft] who gives them long-term stability. They have a terrific front office, and Belichick has the most unique system in football where he can survive a talented player leaving because he’ll plug another player into that hole. Look at what they’ve done with possession receivers, right? They always find a new one, and on third down, that player’s always open.

They have a unique formula because they’re so good on talent assessment and so good on evaluating where cap money needs to go to sustain a victorious team.

You represented Drew Bledsoe, who was one of the biggest casualties of Belichick’s system when he got hurt and Tom Brady took over. What was it like for you and Bledsoe going through that crazy turn of events?

It was tough. [Bledsoe] loved the Patriots, and they had been to the Super Bowl together. He’d been a Pro Bowl, so they’d been very successful. But different teams have different possibilities in terms of whether or not an injured player retains his position when he comes back to health. For some people, it’s the original starter. For some, it’s the hot hand.

Obviously, in retrospect, you would say the Patriots made the right choice because they kept probably the greatest quarterback ever. It’s tough. But at the same time, Bob Kraft had treated him really well. Drew had great memories there, and this is football.

Speaking of the business of football, Patriots didn’t do any big spending this season after shelling out a lot of money in free agency last year. Would you say this is more their “MO” — waiting for players to come to them on cheaper deals rather than paying for top talent?

Not necessarily. They’ll pay market value. But Tom Brady took a discount for years. They had the advantage that he was not the highest-paid quarterback. The result was they had enough cap room to win, win, win. He goes down in history as the greatest quarterback and is exceptionally wealthy anyway. So they got a break with that.

But the problem with having massive talent in the NFL is that it’s impossible to hold it all together. A team cannot have five All-Pro offensive linemen. If you pay them all what they’re worth, you don’t have enough cap room. So it’s understanding which positions need an A or A+ player and which positions need a B or B+ player.

You also represent Chiefs quarterback Patrick Mahomes, who is about to come into a 10-year, $450 million contract starting this year. A lot has been made of the Chiefs trading away Tyreek Hill instead of paying him and saying Mahomes should’ve taken less money, like Brady, to keep the team together. How do you balance paying players what they should be paid while keeping teams together?

They did keep the team together (aside from Hill). In other words, these guys are motivated by winning. People forget how hyper-competitive they are.

And the dollars we’re talking about — NFL quarterbacks now get paid exactly like the superstars in other sports, which had never happened before. Whether somebody’s at $35 million, $40 million, $50 million, every new contract is going to be bigger. Whoever’s up for an extension and is a franchise quarterback is going to push the market.

When the Justin Herberts and Joe Burrows of the world, Lamar Jackson, redo their deals, they’ll continue to push the parameters.

Over time, the Patriots have built up this reputation as a team that isn’t “fun” to play for. What have you heard from the players you’ve represented or other players around the league about what it’s like to play in New England?

That players are happy. Belichick is a tough coach, but he gets results. They put a premium on winning and winning every year, which puts pressure on people. But by and large, players are in football to win, and there’s no more winning organization than them. Going to the playoffs every year, competing for the Super Bowl. The happiest players you have, as someone representing athletes, are players who go to the playoffs and the Super Bowl. They’re the most fulfilled. [The Patriots] do all that. Bob Kraft is a warm owner who gets personal with the players.

Brady was the exception after all those years, but you won’t see a lot of people fleeing a situation that may have high expectations, tough coaching, but results and winning.