SAN DIEGO — Almost every baseball winter meetings has at least one major storyline involving agent Scott Boras and this year’s edition, which officially kicks off Monday at the San Diego Convention Center, is sure to be the same. This, in fact, might be the greatest crop of Boras free agents in history and that’s saying something.

With third baseman Anthony Rendon and starting pitchers Gerrit Cole and Stephen Strasburg, Boras has the three most high-profile players on the market. In addition, he has lefties Dallas Kuechel and Hyun-Jin Ryu. Infielder Mike Moustakas has already signed with Cincinnati for four years and $64 million.

That’s a group that could bring in nearly a billion dollars in contracts for Boras.

Phillies general manager Matt Klentak (left) helps Bryce Harper slip into red pinstripes last March in Clearwater, Fla. as agent Scott Boras looks on. The Phillies would love to repeat this scene with Washington third baseman Anthony Rendon joining them this offseason.
YONG KIM / Staff Photographer
Phillies general manager Matt Klentak (left) helps Bryce Harper slip into red pinstripes last March in Clearwater, Fla. as agent Scott Boras looks on. The Phillies would love to repeat this scene with Washington third baseman Anthony Rendon joining them this offseason.

For the longest time, the Phillies declined to bid on Boras’ big-money players, but that has changed in a major way since John Middleton has become the Phillies’ managing partner. Middleton gave Jake Arrieta a three-year deal worth $75 million two spring trainings ago and Bryce Harper $330 million over 13 years last spring training.

Now, the Phillies’ front man must decide if he wants to buy from Boras’ high-end market again in 2020. He should, of course, because you don’t start a swim across the English Channel and decide to stop halfway. Sure Middleton could be taking the Phillies into the unchartered waters of passing the $208 million luxury tax threshold that comes with a 20 percent tax penalty, but it’s a trip the Phillies need to take.

A USA Today report indicated late last week that the Phillies intend to pursue Rendon despite the luxury tax ramifications and a baseball source told me that he expects the same. The competition could be more fierce for Rendon than it was for Harper because the Los Angeles Dodgers are expected to be more aggressive in their pursuit of the third baseman than they were for Harper. The Texas Rangers are also in pursuit of Rendon, who is a Houston native.

“They just dumped two infielders, so they obviously have a need there,” the source said. “I have to think that Harper would love to have him there and he is talking to him.”

That is an excellent point. Harper was not bashful at all about his desire to play with Mike Trout before the South Jersey superstar signed a record $430 million contract extension with the Los Angeles Angels just a few weeks after Harper signed with the Phillies. Now, Harper has a chance to recruit a former Nationals teammate who has the same agent. The Phillies should encourage him to do so. Ultimately, it will come down to the money and whether Rendon is willing to switch from Washington to a division rival, but a little recruiting never hurts.

Middleton has the money. He said when Gabe Kapler was fired that “I’m not going to go over the luxury tax so we have a better chance to be the second wild-card team. That’s not going to happen. I think you go over the luxury tax when you’re fighting for the World Series. If you have to sign Cliff Lee and that puts you over the tax, you do it. If you have to trade for Roy Halladay and sign him to an extension and that puts you over the tax, you do it. But you don’t do it for little gain.”

A lineup with Rendon, Harper, J.T. Realmuto, a resurgent Rhys Hoskins, Jean Segura, a healthy Andrew McCuthen and an improving Scott Kingery would make a deep postseason run possible.

Asked if he thought the Phillies were close to being a World Series team again even before the hiring of Joe Girardi as manager and the signing of pitcher Zack Wheeler, Middleton said, “I don’t think we’re that far away.”

Some might argue that the Phillies are better off going after one of the premier pitchers still on the market because they have other ways to fill the recent vacancies left by the departures of second baseman Cesar Hernandez and third baseman Maikel Franco.

That is true to some extent. They can sign Didi Gregorius to a deal that figures to be a lot cheaper than the one it will require to land Rendon. They could move Segura to third base or second base, depending upon where they think Kingery fits best.

But let’s face it, Gregorius, Segura and Kingery are not Anthony Rendon. Not even close.

Another argument against Rendon is that top prospect Alec Bohm is on the fast track to the big leagues and will be the third baseman of the Phillies’ future. Bohm, 23, has given the Phillies plenty of reason for optimism, but he also has not played above double-A Reading and needs more seasoning.

Regardless of how well Bohm performs this season, he will not arrive in the big leagues as a better player than Rendon, who at 29 figures to have plenty of great seasons ahead. It took time for Rendon to become an MVP-caliber player and it will take Bohm time, too.

Something else to consider is that the National League might not be too far away from adding the designated hitter. A lot of baseball people expect it to happen in 2022, which will be the first year of the next collective bargaining agreement.

By signing Rendon, the Phillies would get ahead of the DH curve by putting together a lineup that would also include Harper, Hoskins and Bohm, four guys capable of hitting 30-plus home runs. That is a necessary ingredient to compete in a league with a DH. For proof go look at the lineups the Yankees, Astros, Red Sox, and Twins put on the field on a daily basis.

Since general manager Matt Klentak’s arrival, the Phillies have preached position flexibility and it would helpful for the near future if Bohm spends some time working in left field field. He can already play first base.

The fact that the Phillies are thinking big is good. If Middleton’s private jet can land Rendon in Philadelphia a year after his team signed Harper, it would show exactly how much the team’s most visible owners wants the World Series trophy back at Citizens Bank Park.