PORTLAND – First inning. Runner in scoring position, with two outs. Will Middlebrooks stepped to the plate last Monday night in a situation in which he is supposed to deliver.

Middlebrooks, 22, the third base prospect who signed for nearly a million-dollar bonus, is a touted five-tool player now suiting up for the Portland Sea Dogs, Boston’s Double-A minor league affiliate.

The promise is there. Much is expected.

With the runner leading at second base, Middlebrooks took his cut and popped out to the first baseman in foul territory.

Middlebrooks calmly removed his helmet and placed it on the ground, along with his bat and batting gloves. Looked like the kid could care less.

But Middlebrooks, for a while, cared too much, took struggles too personally. He would wonder what was wrong and search for a fix. He wouldn’t throw a bat, but he would churn inside.

“I’m my biggest critic,” Middlebrooks said.

Now, Middlebrooks tries to move on and appears on the verge of breaking out with the Sea Dogs. He’s currently hitting .283 with seven home runs.

Like a lot of young prospects, especially those drafted out of high school, Middlebrooks is attempting to master the fine baseball art of handling failure.

From teenage superstar to just another scuffling ballplayer with a .187 batting average.

That is what Middlebrooks was hitting five weeks into his first pro season in 2008, playing for the Lowell Spinners, the lowest of the three Class A minor league levels.

“I didn’t know how to deal with failure,” he said. “I jumped out there. I was ready to go and boom, I wasn’t getting hits. I was struggling.

“I was in a slump and I didn’t know what they felt like.”

And why should he? Middlebrooks batted .555 his senior year at Liberty-Eylau High School in Texarkana, Texas.

He had the golden touch. Star football and baseball player. He quarterbacked Liberty-Eylau to the state championship. (It did not hurt having running back LaMichael James, now at Oregon, in the backfield.)

Middlebrooks received a football/baseball scholarship to Texas A&M. The only question seemed to be which sport would he make his career.

When it came time for the 2007 major league draft, Middlebrooks was considered a first-round or supplemental-round pick. But there were concerns about being able to sign Middlebrooks. He did have that scholarship in hand and his parents, both teachers, would surely be pushing the college route.

So Middlebrooks dropped down to the fifth round, where the Red Sox took a chance. Now it was up to Middlebrooks.

“A tough decision, but I knew what I wanted to do. I wanted to go play,” he said.

Middlebrooks signed for a $925,000 bonus, the highest given to any Red Sox draftee that year. He signed in August, too late to play that season.

It was easy to see why Boston wanted Middlebrooks. He could hit and, at 6-foot-4, 200 pounds, he would likely develop more power. He could run and, in the field, his glove was quick and his arm a cannon.

“The first thing that stands out is his athleticism,” said Sea Dogs hitting coach Dave Joppie. ” You can just see it. He’s a well-rounded athlete. He’s starting to grow into his frame and get much, much stronger.”

But strength between the ears is equally vital. Former major league pitcher Bob Tewksbury serves as the Red Sox sports psychology coach. Tewksbury said many young players have to face “internal distractions,” including unrealistic expectations as well as “failing for the first time.”

Middlebrooks credits Tewksbury and others like Gary DiSarcina, then the manager of Lowell, with showing him the way. The message: Instead of worrying about every at-bat, just keep working.

It has been a process. For the last three seasons, Middlebrooks has been managed by Kevin Boles — in Class A Greenville, advanced Class A Salem and now Portland.

“When he was younger, he’d have a tough night and it would carry into the next night,” Boles said. “But he’s matured quite a bit and has been able to turn the page real quickly.

“Having some failure or having a tough game or a string a tough games builds a little bit of character … some toughness.

“For these guys to be mentally tough, to play at Fenway Park someday, we expect there are going to be ups and downs. It’s how they handle it.

“Do they push through and fight or does the guy feel sorry for himself? He’s definitely a fighter, one of those guys who wants to improve and keep working at it.”

The improvement continues as Middlebrooks hits better every season, each year at a higher level. His strikeout ratio, once an issue, keeps declining, down to 41 times out of 158 plate appearances, so far this season.

The improvement is a result of work and commitment. In spring training every morning at 7 a.m., before the scheduled workouts began, he met with Joppie in the batting cage.

“Put together some solid routines,” Joppie said. “He’s starting to trust his abilities a lot more.”

In the field, Middlebrooks, a shortstop in high school, looks more and more comfortable.

Middlebrooks jumped out with a .347 average and four home runs in April. That pace has slowed, but without much analysis from Middlebrooks.

“The past two weeks I know I have not been hitting the ball well. But I know that’s baseball,” he said. “These pitchers are here for a reason. They know how to get you out. They’re not just 16-year-old kids throwing fastballs to you.”

And neither is Middlebrooks an 18-year-old clubbing those fastballs at will. He’s now a pro, growing up, seeing baseball as both a game and career.

“I worked my tail off to be prepared physically and mentally,” he said. “Just being able to stay positive, have fun and realize it’s still a game.”

Even when you fly out with a runner in scoring position.

Think Middlebrooks learned his lesson?

In that Monday game, Middlebrooks batted again in the third inning with a runner on base. Middlebrooks took another cut and watched the ball clear the center-field wall.

“He’s getting stronger,” Joppie said. “He’s getting a lot more confident. His tools are coming to the forefront.

“He has a very good chance to be a very special player.”

Staff Writer Kevin Thomas can be contacted at 791-6411 or at:

[email protected]

Twitter: ClearTheBases