John W. Henry is fighting – or, more accurately, typing – on two fronts right now.

Henry and Red Sox General Manager Ben Cherington have travelled to Seattle to meet up with their brow-beaten Boston club, setting off rumours – quickly denied by Henry by e-mail – that manager Bobby Valentine’s ill-fated tenure could be close to its end.

Whilst taking to his laptop or mobile device to answer reporter’s e-mails, Henry tapped out an open letter responding to the concerns created by Liverpool FC’s lack of transfer activity at the deadline and their 2-0 defeat by Arsenal on Sunday that condemned the team to their worst start to a season in 50 years (after three league games, that is).

No one ever said owning a sports team was easy and being part-owner of two of the most iconic makes you a lightning rod for criticism when things are not going well.

And it’s fair to say things definitely are not going well for either team.

Boston did at least receive a stroke of luck recently courtesy of the new ownership group in Los Angeles. A week ago I was pondering the Dodgers’ trade for Gonzalez, Crawford and Beckett, querying whether the Red Sox’s owners could be fortunate enough to find a willing partner to rid their English football team of a similarly burdensome contract or two.

QPR were the obvious free-spending match in terms of ownership bravado; however they didn’t play the Dodgers’ role and come to Liverpool’s rescue. Instead it was Big Sam Allardyce’s renowned love of a big man up front that won the day and saw Andy Carroll move to West Ham. Jordan Henderson and Stewart Downing remain on Merseyside with their transfer fees being a running joke for the rest of us.

Player contracts and transactions work quite differently in baseball and football. The Red Sox were able to completely wash their hands of players who, fairly on them or not, had outstayed their welcome.  Although Liverpool were able to move Carroll’s £80k per week off the wage bill by loaning him to West Ham, that has only provided them with a temporary respite from their £35m mistake and the wage money saved plus the £1m or so loan fee in return doesn’t amount to much money to ‘invest’ in new talent.

Henry had the courage to write of “our own mistakes in a difficult first two years of ownership”, describing it as “a harsh education”.  The money spent by the team on British players can certainly be filed under the ‘mistake’ heading.

There is some value in ‘buying British’ and primarily the premium appears to be paid on the basis of the reduced level of risk against a foreign recruit being able to settle in the country and to perform well in the English game. However, considering the size of that premium, this isn’t exactly a market inefficiency that Liverpool has exploited.  There were no obvious sabermetrics, or soccernomics, principles being applied to Liverpool’s dealings.

Instead, from the outside it looked like Henry and his fellow owners took their ‘football newcomer’ tags to their hearts. Specific players were targeted by Damien Comolli, the former director of football, and Kenny Dalglish and the ownership group put their faith in their employees by backing them irrespective of the cost (presumably within some sort of overall budget limit).

In this respect, Andy Carroll perhaps can be seen as the equivalent of Carl Crawford.

John Henry made some surprisingly frank comments back in February in which he stated he was ‘personally opposed’ to the Crawford contract. He actually made some sound points on the Red Sox not needing additional left-handed hitters, but they got drowned out by the noise of the soundbite quote.

Similarly, Henry initially justified the Andy Carroll transfer price by describing it as a move in tandem with the sale of Fernando Torres, claiming that the price for Carroll was simply going to be £15m less than the price they received for Torres.  That sounds logical enough, yet things are rarely quite that simple. When you pay £35m for someone, you place an enormous amount of pressure and expectation on them. Had they only received £25m for Torres, the £10m Carroll might well have flourished at Anfield.

You could also bring Clint Dempsey into the equation. Henry’s statement in his open letter that “our ambitions do not lie in cementing a mid-table place with expensive, short-term quick fixes that will only contribute for a couple of years” has quickly been interpreted as a knock against the American, who signed with Spurs on Friday after Liverpool refused to pay Fulham’s asking price.

That interpretation is most likely correct, yet, as with Crawford, the media focus will be on the alleged ‘slight’ rather than a clear assessment of the situation, one in which they are learning from their mistakes and focusing on “getting maximum value for what is spent”.

Henry will be pilloried for his statement as that’s just how things work, sadly. Remain silent and you are criticised for being a Yank that ‘doesn’t understand football’ and isn’t taking a full interest in the club; make a statement and you’re criticised for being a Yank that ‘doesn’t understand football’ and is now interfering.

The suggestion that he and his fellow owners might be taking advice from “internet nerds who sit at laptops downloading football manager software” is also a depressingly inevitable reaction from such an insular sport that sadly seems to treat with suspicion anyone that flirts with having something vaguely intelligent to say about it (which is presumably why TV companies hire the likes of Robbie Fowler to appear as pundits and then see no problem at all in them merrily admitting, as Fowler did on ESPN this past Saturday in respect of Jack Rodwell, that they haven’t actually seen much of the respective player that they are providing their ‘expert’ opinions about).

Perhaps Henry and co. bought Liverpool in part so that if things weren’t going well with Boston they could at least focus on the positives on their other team, and vice versa.  If so, that plan hasn’t worked too well so far.

Not so much twice the joy, more double the trouble.