John Henry and the Red Sox just can't win with their mega-contract signings.

John Henry just can't win. I'm not talking about on the field, although his Red Sox haven't finished first in their division since 2018, with three last place finishes during that time. The Red Sox have even won 20 out of 39 games so far this year – good enough to have them just two games behind the Yankees for first place.

What I am saying is the Red Sox, simply, can't win with their personnel decisions. Maybe it is a new curse. Maybe the Curse of the Bambino has been replaced with the Curse of the Panda? Maybe it goes even back a few years earlier. Maybe we can call Boston's recent horrible track record of contract signings the Curse of Godzilla?

Ever since Theo Epstein signed Daisuke Matsuzaka in 2007 to a six-year, $103 million contract, money hasn't been very well invested in players at Fenway.

Remember all the hoopla around that? Who was this guy? Rumor had it he threw like twenty different pitches – all of them effectively. He had this one pitch he invented called the "gyroball." It was unhittable. The pitch went up and down, to the the left and to the right and back left again, and it changed velocities in mid-flight.

What about Matsuzaka himself? No one knew what he looked like. Was he six-foot-five? How old was he?

There was so much mystery that surrounded him. Everyone was on pins and needles as they tracked his flight on John Henry's private jet from Japan to Boston.

Daisuke wound up being a decent pitcher. The Red Sox won the World Series his rookie year, but he showed control problems that would plague his career. He contributed 15 wins that year despite a lackluster 4.40 ERA.

His second year was far and away the best of his career. He went 18-3 with a 2.90 ERA. He finished fourth in Cy Young voting that year.

That was as much as the Red Sox got for their $100 million-plus investment. Matsuzaka was 17-22 during the final four years of his contract, compiling a 5.53 ERA and 1.54 WHIP. Hey, on the bright side, I got to see him pitch a few times at Pawtucket.

Someone else who I watched A LOT at Pawtucket soon after Dice-K's career in Boston ended was Rusney Castillo. Similar to Matsuzaka, Castillo was a mystery and a myth to many. He could do it all, they said – hit for power and average, steal bases, play great defense in center field.

The Red Sox signed Castillo to a seven-year, $72.5 million contract in August of 2014 – only weeks after he set foot in the United States for the first time for a workout for major league teams at the University of Miami.

I got to spend plenty of time over the next seven years watching Castillo close up from the grassy berm beyond the center field fence at McCoy Stadium in Pawtucket.

Castillo did play 80 games for the Boston Red Sox in 2015. Other than that season, Castillo only played 19 other games for the big club. He did play 467 games for Pawtucket. I would have said that Castillo was a great investment for the PawSox, but the team moved to Worcester soon thereafter. Thanks, Larry Lucchino.

In between Castillo and Matsuzaka, there were other bad contracts. There was Carl Crawford (seven years, $142 million), Adrian Gonzalez (seven years, $154 million), and Hanley Ramirez (four years, $88 million).

Even extending fan favorite Dustin Pedroia (eight years, $110 million) didn't turn out good. Pedroia's career was cut short by injuries. The hard-nosed second baseman played his last full season in 2017, but he continued to get paid for four more seasons until his contract expired after 2021.

The worst contract of them all, to me, during this era was Pablo Sandoval. Sandoval was a portly – to put it kindly – third baseman who was affectionately known as "The Big Panda." In 2014, the Red Sox signed him to a five-year, $95 million contract as a free agent.

Sandoval was a converted catcher. His frame showed it. He is listed on Baseball Reference as 5'10", 268 pounds. I will let you see for yourself, below.

Sandoval would only play 161 games for Boston. Many would say that was too many. He was never known as a power hitter in San Francisco, but he did hit for average there – three times hitting above .300. He only managed to hit .237 for Boston with 14 home runs and 59 RBI. What does that equal out to – almost $2 million per RBI?

I almost feel sorry for piling on Sandoval, but his biggest claim to fame in Boston is, probably, the time his belt snapped on a swing against knuckleballer R.A. Dickey.

In the years since Sandoval left town, the string of bad contracts has continued. There has been David Price (seven years, $217 million) and, arguably, Chris Sale (five years, $145 million).

The Red Sox took a shot at an international player again when they signed Masataka Yoshida to a five-year, $90 million. To this point, that has been a disaster.

More telling, in recent years, are the players the Red Sox have chosen not to extend or re-sign.

The biggest misfire was trading away Mookie Betts. Betts was only 27 when the Red Sox traded him to the Dodgers for fear of not being able to, or not wanting to, sign him to a huge, long term contract.

Betts has continued his upward trajectory – as should have been expected from a player entering the prime of his career – with the Dodgers.

After losing Betts, the Red Sox front office faced a lot of pressure to not let another homegrown talent – Xander Bogaerts – leave town.

Bogaerts was different from Betts as Bogaerts could have been viewed as being in the latter stages of the prime of his career. Bogaerts was almost 30 years old. His value was enhanced by playing a premium position – shortstop. However, it was obvious a change in positions was in the near future as his range – which was never that great to begin with – was diminishing.

Give Boston credit on this one as Bogaerts has not lived up to his contract with San Diego. He has switched to playing second base and his offensive production has dipped, dramatically.

Nonetheless, after losing Betts and Bogaerts, the Red Sox could ill-afford to see Rafael Devers walk, especially from a PR standpoint. There were already rumblings that John Henry had become cheap. They were more than rumblings.

From John Henry's point of view, it was totally understandable to put away the wallet. He had gotten burnt time after time after time.

Manny Ramirez may have been the last worthwhile mega-contract the Red Sox signed. Even in that case, Manny was signed in December of 2000 – before John Henry even bought the team.

Maybe you could argue J.D. Martinez was worth it. Maybe.

It's really hard to think of any other Red Sox players, signed during the John Henry years, that lived up to their big contracts.

But Henry couldn't run the Red Sox like he did the Florida Marlins back in the day. This is Boston. The media and the fans pay attention around these parts. They have extremely high expectations and the fans, particularly, expect to be entertained all season long, and beyond.

After not making any significant moves in 2020 and 2021, the Red Sox waited until late into the offseason of 2021-22 to sign Trevor Story – after no one else wanted him – to a $140 million contract. Again, Henry would get burnt as Story is yet to play over 100 games in a season for the Red Sox.

Yoshida seemed like a cheap way (only $90 million) to get a bit of positive press in 2023, but everyone had their eyes on what Henry would do with Devers. The offense was already decimated with the losses of Mookie Betts and Xander Bogaerts. Players like Alex Verdugo, Hunter Renfroe, and Adam Duvall were not anywhere close to adequate replacements.

The Red Sox could not afford to lose Devers – no way, no how. The negative publicity would have, most likely, run John Henry out of town.

So, despite concerns about Devers' weight (see Pablo Sandoval, above) and his defense at third (see, also, Pablo Sandoval, above), the Red Sox locked Devers up for an extension of ten years and $313 million. Fans and media were placated.

But not Devers. Devers has barely started playing under his new contract and already John Henry may be regretting it. It has nothing to do with his on-field performance. Devers is still, by far, the most dangerous hitter on the Red Sox. He is proving, however, to also be the most toxic.

That's the danger of giving that much money to someone Devers' age and maturity level. The Red Sox' hope was that they had locked up their next David Ortiz.

It is always great to lock up a talent like Devers when they are young, but these are the pitfalls of creating an entitled enigma. No one really knew how Devers would respond to now being the leader of the team. David Ortiz he is not in this category, at least.

The Red Sox' big splash of the 2024 offseason was Alex Bregman. Again, Boston waited until the last second to make their big signing, but fans were ecstatic they did something.

On paper, Bregman made the team better, offensively and defensively – that is, if he played third base where he has his entire career and won a Gold Glove there just last year.

But Rafael Devers has been Boston's third baseman for the last eight-plus seasons. Who cares that he led the league in errors at his position seven of those seasons?

When asked in spring training if he would entertain the thought of giving up third base and be willing to become a full-time DH, his one word response was, "No."

The Red Sox closed their eyes and named Alex Bregman the starting third baseman before the season opener. When they opened an eye to peek, Devers put down his glove, picked up his bat, and moved on without saying a word. I am sure Red Sox management breathed a sigh of relief.

Devers got off to a historically horrid start to the season. He was hitless in his first nineteen at-bats, striking out fifteen times. He has rebounded since – getting his average up to .255 while hitting six home runs. He leads the majors in walks with 29.

Everything seemed to have settled down. Then Triston Casas blew out his knee running down the first base line on a meaningless play on May 2 against Minnesota.

First base happens to be Boston's Achilles Heel in that they have no depth in the minors at the position. Sure they have stars-in-waiting in Roman Anthony, Kristian Campbell, and Marcelo Mayer. None of them play first base.

The suggestion has been made to maybe try one of them at first base, especially Anthony, who has proven that he is more than ready to be in the majors. Moving any of these youngsters from their natural position this early in their careers is foolish. Changing positions is something you do to an aging player who has proven he can longer play the position he has been playing his entire career.

Hmmm. Who could fit that bill for Boston? Who would help the team out the most by picking up a first baseman's glove and giving it a go? Romy Gonzalez? Abraham Toro? Connor Wang? Nope. That would be of no help.

Hey, I just thought of someone. How about Rafael Devers?

Would he entertain the thought – being the team leader his enormous contract dictates he should be? "No."

That was the one word answer he gave to the media, again.

Poor Devers. He claims he has just adjusted to his routine of being a full time DH. How hard was that? What did that entail? Knowing how many bags of sunflower seeds he can eat while his team is on the field? Knowing how long he can hang out in the clubhouse between at-bats?

$313 million just doesn't go as far as it used to.

On a side note, I used to run a fast food restaurant. At the beginning of COVID, we raised our minimum wage to $15/hour. Only months prior to that, most of my employees were making about $11 or $12 per hour... and they always complained about it.

After these high schoolers got their substantial raises, you want to know how many times I'd hear one of them say in response to me asking them to change trash barrels or, God forbid, clean a mess in the restroom, "I don't get paid enough for that."

You would think Devers was being asked to clean a toilet the way he responded to being asked to play first base. The Red Sox and John Henry are going to pay the man, at least, $313 million when all is said and done.

If John Henry, or any member of his management team, asked Devers to mow the lawn at Fenway or to sell popcorn at the concession stands during games, Devers should put on some gardening gloves or an apron and go do it.

I feel for John Henry, or any owner of a professional sports team. You just can't win. If you let someone like Betts or Bogaerts go, you get annihilated by the press. You decide to appease the masses and sign a young superstar like Devers, and you get annihilated in the wallet.