You couldn’t ask for a better place to hit than Colorado Springs. Last year, the hometown Sky Sox batted .305/.366/.489 as a team and allowed a 6.49 ERA as a team. It’s the craziest place to hit in the craziest league to hit, and it’s where Brandon Wood is hitting .253/.289/.418, with 19 strikeouts and three walks. It’s his age-27 season.

It’s wrong to say that age-27 is the magical year when everybody sets new personal bests. Some hitters peak in their 30s and some in their early 20s and some when they’re 25 and some when they’re 29. Twenty-seven is just a number, and when it starts a sentence, a hyphenated word. It’s only as significant as you make it.

But, since Bill James wrote in 1982 that “both pitchers and non-pitchers attain their greatest aggregate value at the age of 27,” 27 has been a year that means slightly more than 26 and 28. It’s the last year that a former prospect qualifies as a post-hype sleeper. It’s the year when, if you hit .253/.289/.418 in the PCL, smart people will probably quit writing Spring Training love letters calling you the comeback kid. Twenty-seven is the year that failed ex-prospects update their passports and start thinking about playing in Japan, or playing in Mexico, or playing in Korea, or backpacking in Europe. There are late bloomers in baseball, plenty of them, but they usually did something in their age-27 season. Nelson Cruz slugged .695 in Triple-A when he was 27. Jack Cust had a .467 OBP in Triple-A when he was 27. Bryan LaHair had a .942 OPS in Triple-A when he was 27. Brandon Wood, who had a .970 OPS in Triple-A when he was 23, has a .707 OPS in Triple-A when he is 27. Not everybody keeps getting better, and 27 tells us, with something near finality, who is just getting worse.

These are five of the saddest age-27 seasons in modern memory.

5. Dee Brown, 2005
Age 21: .353/.440/.591 (Double-A)
Age 27: .206/.274/.360 (mostly Double-A)

Brown spent four years on Baseball America’s top 100, peaking at No. 11 after rolling through Double-A, where he was the sixth-youngest player to get 100 plate appearances in the Texas League. Like Wood, he got three cups of coffee before finally getting a chance to start regularly in the majors when he was 23. He never managed a .300 OBP in the majors, he never slugged .400, but into his age-26 season, he was still getting sporadic chances to earn a job, starting half of Kansas City’s games in the second half of 2004.The Royals cut him loose after that season. He was signed and released by the Devil Rays before the 2005 season began, and he was signed and released by the Yankees before the All-Star break, and he was signed and released, by the Nationals before Halloween. He spent that age-27 season mostly in Double-A, where he walked four times in 220 plate appearances. His OPS in Double-A was only slightly better than the .556 OPS that Michael Jordan put up in Double-A. That was a half-hearted basketball reference.

Now: He spent the past two years playing for the Saitama Seibu Lions but is no longer listed on the team’s roster.

4. Chad Hermansen, 2005
Age 21: .270/.321/.530 (Triple-A)
Age 27: .182/.341/.424 (Mexico)

Hermansen spent five years on Baseball America’s top 100, four of them in the top 50, and peaked at No. 13. By 26, though, he had played for four major-league teams, earning progressively fewer plate appearances with each: 458 for the Pirates, 49 with the Cubs, 27 with the Dodgers, and just seven (hitless) with the Blue Jays. In 2005, his age-27 season, he batted .181 for Campeche, in the Mexican League. A washed-out Ruben Rivera had a 1.053 OPS for Campeche that year. The ERA title in the Mexican League was won that year by a 40-year-old Isidro Marquez. The Mexican League is not a stepping stone, so much as a net, and not so much a safety net as a trapping net. There were 12 players on that Campeche team who played in the majors, but not one of the 12 did so after playing for Campeche, and on average those 12 had been out of the majors for five seasons.

Now: Hermansen is an instructor at Frozen Ropes, according to his company bio. He played his final minor-league game when he was 29.

3. Scott Kazmir, 2011
Age 21: 3.77 ERA (Majors)
Age 27: 19.73 ERA (mostly Triple-A)

Kazmir never actually played in Triple-A when he was on his way up. He had a 1.73 ERA in Double-A when the Mets traded him to Tampa Bay and a 1.44 ERA in Double-A when the Rays called him to the majors at age 20. After allowing five runs in five outs in his first 2011 start with the Angels, though, he spent his first extended period in Triple-A while rehabbing. Between that one start in Anaheim, five starts in Salt Lake, and one start in the Venezuelan Winter League, he allowed 39 runs in 17 innings in 2011. Opponents had a .540 OBP against him. During the same season, the Angels’ 25th-round pick, a college pitcher named Joshua Alvarado, had a 10.61 ERA and walked 17 batters in nine Arizona League innings. Who do you think pitched better in 2011, Kazmir or Alvarado? I’m not very confident about either answer.

Now: Has tried out for teams but hasn’t signed. Tweets things like this:

2. Andy Marte, 2011
Age 21: .275/.372/.506 (Triple-A)
Age 27: .202/.278/.328 (Triple-A)

“The best prospect in baseball and a future superstar,” we wrote in BP2005. “In his prime, expect a few seasons of Adrian Beltre, circa 2004.” A few seasons. A few of them! His prime never happened, and by his age-27 season we described him as “slow and stiff, (with) a bat too slow to catch up to better fastballs.” His PECOTA comps, tantalizingly to the truly delusional, included Jose Bautista at the top, but Marte couldn’t hit even the middle-aged junkballers of the International League. Pirates third basemen hit .224/.276/.333, the second-worst line in the NL in 2011, but in his age-27 season, Marte wasn’t even good enough to join in that disaster.

Now: Actually, not sure. He filed for free agency in November 2011, and that’s our last transaction for him. The Indianapolis Indians told me they “honestly have no idea where Andy Marte is or where he went.”

1. Brien Taylor, 1999.

Age 21: 3.48 ERA (Double-A)
Age 27: N/A (Extended spring training)

The Brien Taylor story—one of the greatest pitching prospects ever, injured in a fight, never made the majors—is well known. He didn’t just stop pitching after the injury, though. He kept pitching, almost unfathomably poorly. He walked 175 batters in 109 innings during the four seasons after the injury but still attracted a minor-league contract with the Mariners in 1999, his age-27 season.

“I’m a lefty and I still bring the ball 90,” he said in an Associated Press story. “He’s a lefty with arm strength,” said the Mariners’ director of player development. But he never pitched anywhere other than extended spring training that year, and the Mariners cut him in June. The team didn’t even announce the move. “It happened early this month,” one newspaper article said on June 27, 1999, “but nobody said anything about it until Saturday.” Taylor got one more chance, at age 28, and walked nine batters in 2 â…” innings in the South Atlantic League.

Now: Has one of the saddest Wikipedia sections existent, which is probably best summed up by this line: “Taylor still lives with his parents, at the end of a street named after him.”

Honorable mention:

Derrick Gibson, 2002: .248/.324/.393 for Duluth-Superior of the independent Northern League
Lastings Milledge, 2012: .247/.327/.412 for Tokyo Yakult Swallows
Joel Guzman, 2012: .282/.367/.435 so far as DH/1B with Double-A Pensacola
Roger Salkeld, 1998: 5.79 ERA, 64 walks in 82 Triple-A innings
Andy Laroche, 2011: .654 OPS for Oakland, slugged .376 in a half-season in the PCL

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The number of guys on this list with connections to the Pirates is depressing, and even more so because it doesn't include the biggest disappointments of the past twenty years (e.g., Kris Benson, John Van Benschoten, Bryan Bullington).
“Taylor still lives with his parents, at the end of a street named after him.”-- priceless

I wonder if he is as depressed about that statement as I am for him.
Well, if you're to believe the story the Wikipedia entry links to, he's actually taking it pretty well. He built the house they currently live in with his signing bonus, so it sounds like the arrangement is more choice than necessity.

That said, Brien Taylor is probably the second most depressing career path of an African American in organized baseball after Alex Johnson.

Well Brien might now be the saddest. He is now in prison for three years for cocaine trafficking.
That was the saddest line ever.
Taylor got arrested recently for dealing drugs. That's even more sad.
Scott Kazmir now involved in the production of 90210. Coincidentally, that was how many batters he walked during his three years in Anaheim.
You missed Joe Charbonneau. ROY at 25 in 1980,combined 640 OPS at AA/AAA in 82 at the age of 27.
Hank Blalock, All Star at the age of 22 and 23... left baseball at 29