Red Sox biggest missed opportunity, not pursuing Freddie Freeman

Media and fans have been pointing fingers at a lot of people and a lot of transactions as reasons for the mediocrity of the Boston Red Sox in the last few years. Many would say they have been worse than mediocre the last four years. They are currently in last place and if that continues, and there is no reason to believe it won’t, that would mean three last place finishes in the last four years.

Fingers have been pointed mostly at Chaim Bloom. Some fingers have been pointed at John Henry. A few have pointed at Alex Cora.

There have been some questionable transactions the last couple of years. Giving Chris Sales a huge contract extension has so far been a mistake. What were they thinking trading Hunter Renfroe for Jackie Bradley, Jr.? They kept players like Ryan Brasier and Matt Barnes around for way too long. One of their bigger trade deadline deals in recent memory was acquiring the washed up Eric Hosmer. Then obviously, there have been the glaring mistakes - losing home grown stars, Mookie Betts and Xander Bogaerts.

But I proclaim there is one acquisition that would have made the Red Sox playoff contenders each of the last four years! And every time I see this guy smack a double to the opposite field gap, I cringe.

Fans have endured a hideous last two-plus seasons watching the play at first base, both offensively and defensively. Fans have had to endure Christian Arroyo, Bobby Dalbec, and Hosmer playing first base. They have all been deemed as place holders for the Messiah at the position, Triston Casas. Casas made his much anticipated debut midway through the 2022 season and has struggled to hit .200 over 500 at-bats. Even more putrid has been his defense, which was considered a strength in the minors.

Freddie Freeman played his twelfth and final season for the Atlanta Braves in 2021. The Braves appeared to show little interest in re-signing their veteran first baseman. He was available at the trade deadline. Instead the Red Sox traded for Eric Hosmer. Hosmer was never meant to be the long term answer at first base for Boston. Casas was riding steadily through the minors. Hosmer never wound up being the short term answer, either.

It, certainly, would have taken a lot to trade for Freeman, but when you consider the Red Sox have lost players like Xander Bogaerts, JD Martinez, and Nathan Eovaldi for nothing last offseason, you would like to think the Red Sox had some foresight to package some kind of a deal with these expiring contracts and prospects. And, yes, they would have required packaging Casas in a deal with, say, Eovaldi to acquire Freeman. Casa’s trade value was at its highest around that time, and the Braves would have been seeking a replacement for Freeman at first base.

It could be said the Red Sox have been held hostage waiting for Casa’s emergence, much the same way now they are hooking their wagons to shortstop Marcelo Mayer. It is a risky gamble trying to stay in a holding position while waiting for these prospects, who may or may not pan out.

Freeman, meanwhile, has just continued to hit and field. He won the Gold Glove in 2018. Have you seen the Red Sox play defense this year? You think a slick fielding first baseman couldn’t have won a few more games for the Red Sox.

While Casas this preseason made waves by saying his goal for this year was to play 150 games, Freeman has played 147 games or more nine times in his career. You can always count on him to be on the field, and to be productive. He has hit above .295 every year since 2016 and seems to be only getting better.

And the reason I am most bitter about the Red Sox not pursuing Freeman is his hitting stroke. His left-handed bat was made for Fenway. You don’t have to be an MLB scout to see it. He would have tattooed The Wall like no lefty hitter since David Ortiz, and Wade Boggs before that. Freeman has led the NL in doubles three out of the last five seasons and currently leads MLB this year.

And if you want to say the Braves would never have dealt Freeman in 2021 - the Braves did go on to win the World Series that season - I would ask why didn’t they back up the Brinks truck when Freeman became a free agent following that season. The Red Sox certainly wouldn’t have ranked in the bottom tenth of MLB in offensive production for first baseman. The Red Sox would no longer have to worry if Casas was going to live up to lofty expectations. That could have been the Braves’ concern. And if the Braves wouldn’t have dealt Freeman for Casas et al, the Sox then could have packaged Casas in another deal after signing Freeman.

Freeman signed a six-year, $162M deal to play for the Los Angeles Dodgers (who else?) prior to the 2022 season. The deal seems like a steal now with players signing $300M+ contracts this past offseason. The 33-year-old just keeps playing like the future Hall of Famer that he is. So next time you watch a Dodgers’ game - and you can count on Freeman being on the field playing - just imagine what could have been if the Red Sox were more aggressive and locked him up. These last three seasons may not have been as painful.