The New Holliday Lottery

Following the bouncing ball to Stillwater

I did a double take on the corner of 84th St and 3rd Ave. In a pack of pedestrians waiting for the light to change, I saw a familiar face. He had a cup of coffee in one hand and was holding a four-year-old boy in his other arm. Absent the iconic pinstripes he’d wear again in just a few hours, Matt Holliday was still immediately recognizable.

We had friends in common; there were plenty of ways to open a conversation. I had scouted his game the night before.

I elected not to say anything. He was with his son. That time was precious.

If that young boy is anything like his father or big brothers, we’ll be hearing about him in five or six years. Now we don’t need to scout 11-year-olds or put that kind of pressure on a child, but you’re going to stand out — even on a crowded Manhattan street corner — when your big brothers both are first overall draft picks. And that just might be the case for the youngest Holliday son.

In 2022, Jackson Holliday was first off the board, the Orioles’ reward for losing more games than anyone else in baseball the year before.¹ As various outlets publish the earliest projections for the 2025 Draft, there’s a familiar name at the top.

The Nationals scouting department will be spending a lot of time in Stillwater, Oklahoma, this spring, closely watching high school senior Ethan Holliday. Scouts and executives from the Angels and Mariners will likely keep a close eye on the 17-year-old at Stillwater High School, too. It’s the same school where patriarch Matt played before signing as a seventh-round pick of the Rockies in 1998.

The Chicago White Sox lost an all-time record 121 games last season. So why aren’t they in the mix for the projected first overall pick? After all, when Jackson was selected first overall by the Orioles, the right to choose first was earned by losing 110 games and 108 games in consecutive years.

Well, that all changed with the new Collective Bargaining Agreement. For the third year, there’s been a lottery to determine the first six picks of the draft. All 18 non-playoff teams have a chance; the teams with the worst records from the previous season have the best odds of snagging that top pick.

Earlier this month at baseball’s annual Winter Meetings, in Dallas, the balls bounced the way of the Washington Nationals. After finishing the season with the sixth-worst record, the Nats only had about a 10% chance of landing the top pick. Much to the chagrin of the Rockies, Marlins, and Angels, all of which had better odds, the Nationals were the beneficiaries of good fortune.

If you’re wondering how only three teams had better odds than the sixth-worst team, stick with me (and good job reading closely).

If all of that is more complicated than you care for, rest easy knowing that tanking no longer pays.

Three years into the draft lottery, and we’ve seen a favorite, a long shot, and mid-range contender each walk away happy. The one constant, though, is the Hollidays.

Shaking Up The Order

The current Collective Bargaining Agreement, impetus for the 2022 lockout, reflects the shared desire to disincentivize tanking. MLB and the Players Association agreed to no longer reward the worst team in baseball with the first pick of the draft.

Remember the race to the bottom? It’s a strategy that the Astros rode to two championships and two more World Series appearances in a six-year span. The Orioles took full advantage of their draft priority in recent years; losing in bulk between 2018-2021 set them up to reign over the draft hierarchy. Baltimore’s selection of Jackson Holliday marks the final time a team will reap the benefits of losing intentionally and gratuitously. The Holliday family finds itself straddling draft structures.

There’s also a rule to prevent teams from spending too many years atop the draft.

Here’s how the White Sox ended up having their noses rubbed in their record 121 losses: Teams that receive revenue-sharing payouts cannot receive a lottery pick for more than two consecutive years; teams that don’t receive revenue sharing cannot hold a top-six choice in back-to-back drafts. Any club ineligible for a lottery pick — one of the first six picks of the draft — can’t select higher than 10th overall. That rule sent the White Sox and the A’s to the 10th and 11th picks, respectively.

That last paragraph feels like it should be read the fine print read incredibly quickly by a voice-over actor at the end of a commercial. Once again, just know that tanking no longer pays.

After the 2022 season, the Nationals, A’s and Pirates were equal frontrunners for the top pick of the 2023 Draft. The Pirates won the Draft Lottery. They picked the right year.

Pittsburgh used its top pick on Paul Skenes, who debuted on May 11, started the All-Star Game, and was voted National League Rookie of the Year. If he could hit 40 homers as well, he’d be the American Ohtani.

A franchise-altering choice was enabled by the bouncing balls. Yet it was no great surprise to see the 100-loss Pirates on the clock. The teams that received lottery picks for the 2023 draft were mostly expected to receive them.

It all changed one year ago. The favorites to secure the first overall pick were Oakland, Kansas City, and Colorado. The Nationals had a poor enough 2023 season to qualify for the lottery, but the new rules prohibited them from consecutive top-six picks. (They picked second in the prior year and weren’t eligible to pick until 10th at the earliest because they are a revenue-paying team.)

Of course, when the balls were drawn, the Nats had the winning combination. But wait! Hold all tickets! That’s right — you were paying attention to the last paragraph. MLB doesn’t care about taxation without representation. It was time for a re-draw.

Enter Johnny Mac

Much like when the NBA holds its draft lottery, each team sends a team representative to the drawing.

John McDonald was selected out of Providence College by Cleveland in the 12th round of the 1996 Draft. He debuted with the Indians in 1999 and retired after the 2014 season. He spent the majority of his career with Cleveland and Toronto, but in July 2011 he brought his elite glove work to Arizona. I still marvel at some of the plays I saw him make up the middle.

The Guardians had a 2% chance of securing the first overall pick. In parts of two seasons, I saw McDonald make plays on balls that looked like sure base hits. If anyone could snag that two-percenter, it’s Johnny Mac.

So consider that the Guardians had the first overall choice in this year’s draft and went to the ALCS four months later. The baseball gods are happy, no?

And while baseball generally quiets down this time of year, the Nationals are on the clock this holiday season.

More WTP soon! The Player of the Year votes are in.

1. The Diamondbacks also lost 110 games in 2021, but the Orioles “won” the tiebreaker by losing more in the previous year.