David Ortiz urges Red Sox to re-sign Rafael Devers, Xander Bogaerts

The Boston Red Sox should listen when David Ortiz speaks

David Ortiz carries a tremendous amount of respect within the Boston Red Sox organization. He’s among the most significant figures in franchise history as the centerpiece of three World Series championship teams. Ortiz knows what it takes to be a winner and his opinion forged by years of experience matters. So, when Big Papi has something to say about the team’s future, the Red Sox better be listening.

The Red Sox face pivotal decisions regarding their two biggest stars. Xander Bogaerts is expected to opt-out of his contract after this season. Rafael Devers will be eligible for free agency after the 2023 season. Boston didn’t appear to be anywhere close to an agreement during extension talks prior to this season and the sides aren’t expected to negotiate during the season.

During a Zoom call with the media before his induction into the Baseball Hall of Fame, Ortiz stressed the importance of locking up the All-Star infielders to extensions, according to MassLive’s Matt Vautour.

“I hope the Red Sox make sense about the decision we have to make with him. We have to keep Devers around man. He’s the face of the organization as of right now. Nobody can argue that,” Ortiz said. “When you have a guy like him or like Bogaerts in your lineup, that means you’re going to take pressure away from everybody else. They know how to handle it. They know how it is to play in Boston. Trust me. Playing in Boston is not for every type of player. I played there for so long. It’s a distraction for a lot of players. They don’t know how to handle it.”

Ortiz went on to mention that he’s played with teammates who were superstars in other markets but struggled when they came to Boston. Carl Crawford, Edgar Renteria, Hanley Ramirez and Pablo Sandoval stand out as obvious examples. Not everyone is built to handle the pressure of this city, where winning is the only acceptable outcome and every flaw is dissected by the intense media scrutiny.

The Red Sox have a history of splurging on expensive free agents who haven’t been tested in this type of environment but they haven’t shown the same enthusiasm for retaining their own stars who have proven they can handle Boston. Under the current ownership group, Jon Lester, Jacoby Ellsbury and Mookie Betts are among the homegrown stars that the Red Sox let walk away in free agency or they traded them before the players had the chance to leave them. Pedro Martinez and Johnny Damon were key pieces on the 2004 championship team but the Red Sox didn’t put in enough effort to keep them around when their contracts expired a year or two later.

Some of those players didn’t age well on their next contract with another team, so perhaps the Red Sox were wise to let them leave. It still stings when a fan-favorite moves away, especially when we have to watch them thrive elsewhere.

Seeing Devers or Bogaerts provide All-Star caliber performances while wearing another uniform is a nightmare scenario for Red Sox Nation.

The Red Sox can’t let the faces of their franchise get away

Many already seem convinced that Bogaerts has one foot out the door based on reports that he plans to opt-out. That doesn’t mean he’s leaving. We knew from the moment that Bogaerts signed his last extension that he was going to trigger this opt-out clause as long as he remained healthy and productive. He’s on a team-friendly deal and deserves a new contract that aligns with the current market.

Boston’s low-ball offer last spring, which essentially honored the remaining $60 million over the next three years while tacking on an extra year for $30 million, was widely criticized. It’s going to take more than that to get Xander to stay.

Bogaerts isn’t going to get the $300+ million deal that other star shortstops have landed in recent years though. He’ll turn 30 years old in October so a 10-year deal would be wildly irresponsible. If another team is foolish enough to make that offer, so be it. Boston is banking on Bogaerts’ desire to stay in Boston and their ability to match a reasonable offer. It’s going to boil down to the number of years. Four clearly wasn’t enough but there is a limit to how much longer the Red Sox can offer considering his age and the expectation that he won’t stick at shortstop through the duration of his next contract.

It’s a different situation with Devers, who will be just shy of turning 27 when he’s eligible for free agency. With more years of his prime covered by his next contract, a 10-year deal with an average annual value north of $30 million is reasonable for a player who has made the leap into the MVP conversation.

Ortiz paid Devers the ultimate compliment by comparing the young third baseman to himself. He called Devers one of the top three hitters in baseball, a fearless player with a knack for coming through in the clutch. That’s the type of player the Red Sox should lock up to a long-term deal and there’s little reason to believe they aren’t interested in doing so.

There’s no rush though, considering Devers is still under team control through next season. Sure, we would prefer to get the deal done as soon as possible to calm our nerves, but think about it from the player’s perspective. What incentive does Devers have to sign a deal now unless he’s blown away with an insane offer? Why wouldn’t he want to wait and see if his friend Xander is staying in Boston or how much Aaron Judge is going to get paid this winter before he makes a commitment?

The Red Sox aren’t going to hand Devers a blank check. That’s not how this works. It’s a negotiation that will continue after this season. The departure of Betts is a fresh wound that clouds our perspective but the situation with Devers is entirely different. Boston’s future payroll is in a much better position than it was two years ago. As great as Devers is, he isn’t going to command a record-breaking deal that lasts until he’s nearly 40 years old.

With plenty of salary being shed from the payroll after this season, the Red Sox can easily afford new deals for both players. They can each get paid $30+ million next season and still allow the Red Sox to stay within their budget.

History tells us that the Red Sox won’t pay up for their own stars but each scenario comes with a unique set of circumstances. Boston is in a strong position to build around these core players who are in their prime. Both players have shown a desire to stay in Boston. Contrary to popular belief, it would be surprising if the Red Sox weren’t able to retain at least one, if not both, of these star players for the foreseeable future. If they let them both slip away, the Red Sox will have to answer to an outraged fan base that includes Big Papi.