Mark DeRosa And The [Almost] Terrible, Horrible, No Good, Very Bad Day
The USA moved into the World Baseball Classic final last night after beating the [loaded] Dominican Republic national team 2-1 in Miami. The World Baseball Classic, for the uninitiated, is the sport’s version of the World Cup, held every three years.
They owe it all to the most unassuming of teams – Italy.
For those who may have missed it, Italy bailed out the United States in the World Baseball Classic last Wednesday night when they beat Mexico.
Team USA — with a roster that reads like an All-Decade All-Star team – was expected to meet equally loaded Japan in the final. But they ended their first-round games needing the unheralded Italians to beat Mexico to move to the quarterfinals and avoid what would have been one of the most embarrassing sports failures of the last thirty years.
Why the situation came about is perhaps as embarrassing as it is inexplicable: the morning before the US played Italy in the USA’s last pool game, Mark DeRosa, the manager, appeared on MLB Network’s Hot Stove and said this: “It’s weird. We want to win this game even though our ticket’s punched to the quarterfinals.”
Hours later, DeRosa released his starting lineup, sitting five starters and setting up a pitching rotation with the kind of guys you bring in when it’s 11-3 and you want to protect your ‘big arms’ innings and pitch counts for the games that matter. In other words, all the hallmarks of a ‘rest the big guys, see how the game goes, have everyone fresh for the quarterfinals’ game plan.
There was, however, a major problem — the USA had not clinched a quarterfinal berth. By all appearances, someone finally told DeRosa what was really going on during the sixth inning with the US down 8-0. That’s when DeRosa started pinch hitting and brought in some real bullpen help. All too late.
Italy won 8-6. The US was relegated to watching Italy-Mexico and hoping either Italy won outright or Mexico won by four or more runs. Italy, behind a record three home runs by Italian captain and Kansas City Royals star first baseman Vinnie Pasquantini, crushed Mexico. If you listened carefully you could probably have heard DeRosa’s exhale in the air around Houston the moment the final out was recorded.
Here’s the thing about Mark DeRosa: He played sixteen seasons in the major leagues as one of the most valuable utility men of his era — the kind of player every contending team wants, versatile enough to play second, third, the outfield, and do all of it competently while keeping a roster flexible. He was a smart, engaged player who clearly paid attention. When his playing days ended he moved into the broadcast booth and was, by any honest assessment, one of the better studio analysts in the game — knowledgeable, articulate, good on camera.
What he doesn’t know — what nothing in his sixteen years as a player or his years on a TV set prepared him for — is managing. Sure, he managed the 2023 USA team to a loss in the final when Shohei Ohtani memorably struck out his teammate at the time, Mike Trout, to get the save. That was a total of seven games managing experience. DeRosa played sixteen years in the major leagues, that’s enough experience for most players to handle a team for … well, at least seven games. Baseball history is stuffed with interim managers who stepped in for a dozen or so games but in almost every case there was a reason ‘interim’ was never removed from their resumes.
DeRosa walked into a format the sport he knows inside and out simply does not use. And he made assumptions accordingly — assumptions that nearly sank his team.
On to a very different sport but also one involving national teams. Last weekend, the Six Nations Rugby Championship was in its penultimate weekend of games. The Six Nations is an annual rugby tournament featuring England, France, Ireland, Italy, Scotland, and Wales. Aside from the Rugby World Cup, it is the most prestigious competition in the sport.
France went into its weekend game against Scotland looking for another win on their way to a Grand Slam (beating all the other teams) and winning the Cup. They were — like USA Baseball a few days later — heavily favored to rout Scotland in front of 67,100 very unhappy Scottish fans at Murrayfield in Edinburgh.
With ten minutes left, France trailed 50-19. The rugby world was rocked. Their Grand Slam hopes crushed, France kept most of their starters in, subbing in two fresh but highly experienced backs. They threw their game plan out the window, threw all caution to the wind, and poured it on over the last ten minutes, scoring 21 unanswered points.
Why? Because their coaches understood exactly what the tournament’s point differential tiebreaker meant going into the final weekend, where France, Scotland, and Ireland would be locked in a three-way title fight. The 50-40 loss, in fact, helped position them to win the Cup while backing Ireland and Scotland into a corner. France did indeed win the Six Nations Saturday evening.
France played the tournament, not just the game in front of them. DeRosa and the USA staff were managing a game — one they thought, incorrectly, didn’t matter.
So, where are we going with all this? Somewhere we’ve only covered once before in this space — dabblers.
Unlike medicine, the law has no board certification requirements beyond passing the bar. A brand-new attorney can walk out of law school and take on a criminal defense, a complex commercial dispute, a contested estate, a real estate closing, or an employment matter — all in the same week, if they like. No specialty license required. Nobody checks.
Sometimes, for a genuinely straightforward matter, this causes no real harm.
DeRosa’s 2023 experience was relatively simple, a straightforward – there were never any chance tie breakers would be needed. Here’s where we note that Major League Baseball doesn’t have tournaments. It has 162 regular season games followed by a playoff bracket of series — best of three, best of five, best of seven. Every game is effectively zero-sum. There are no tiebreakers based on run differential. There are no pool standings. There is no scenario where you lose a game but score enough runs to move forward anyway.
But the most dangerous moment with an attorney operating outside their depth isn’t when they don’t know something. It’s what happens after they figure out they don’t — because by then, the decisions have already been made. The motions filed. The contracts signed. The provisions that no experienced practitioner in that area would ever have missed, now absent from the record.
Mark DeRosa knows baseball. He just didn’t know this particular version of it, one with extra layers of complexity, and the gap between the two nearly cost his team everything. In much the same way a lawyer who handles contracts every day is not automatically equipped to handle your employment dispute. A litigator who has tried a hundred cases may never have drafted the kind of agreement sitting in front of them. Competence in one field doesn’t easily transfer to another.
In law, as in tournament baseball, catching on in the sixth inning rarely saves the game.
France’s coaches walked into Murrayfield knowing every rule, every implication, every contingency — including the ones that only announce themselves when you’re down 31 points with ten minutes to play. That preparation looks invisible until the moment you need it.
That is what experienced legal counsel does across every area of practice. Not just the rules for today’s hearing or today’s closing — the rules for the whole tournament. What this contract clause means when a dispute arises three years from now? What this business structure means when a partner wants out? What this estate plan looks like when the family is sitting together and the will is being read for the first time.
Hire the lawyers who walked into the tournament knowing all the rules. Before the first pitch.
As for the USA? They await the winner of Italy-Venezuela tonight.
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