FORT MYERS, Fla. — Former major league pitcher Bob Kipper has two daughters, Kaylyn and Kendal, back home in Greer, S.C., with his wife Kristin.

In Portland, Kipper becomes the father figure, mentor and coach to a bunch of 20-somethings that make up the Portland Sea Dogs pitching staff.

Kipper, 46, who pitched in the majors for eight seasons, with the Angels, Pirates and Twins, has coached in the Red Sox organization since 1999, including two stints with the Sea Dogs, in 2003-04 and 2010 to the present.

He offers a lot of advice to his players, the most important one being: Prepare to fail, and learn from it.

“Every pitcher, whether you’re in Salem, Greenville, Portland or wherever in professional baseball, you are going to experience bumps in the road,” Kipper said. “That’s what makes us a better pitcher in the long run.

“It makes us better equipped to go out there and respond to the unfairness and the failures that this game inevitably presents.”

He will give that speech over and over again to his pitchers, especially his starters.

Here is a look at the Sea Dogs’ starting rotation, with views from Kipper.

• Stolmy Pimentel, 21, gets the most attention, as a 40-man roster guy and ranked No. 6 among Red Sox prospects by Baseball America. He is 6 feet, 3 inches, 165 pounds, and he hums it.

“Pimmy has obviously got stuff that’s going to turn some eyes,” Kipper said. “Last year, he was touching 95, 96 (mph), so we’re talking power stuff.

“For his age, he’s always shown an advance feel for a change-up. The curveball shows promise but it continues to be that work in progress.”

Pimentel, a free agent sign from the Dominican Republic, is entering his fifth year of pro ball. He was 9-11 with a 4.06 ERA last season in advanced Class A Salem.

• Alex Wilson, 24, is another prospect (19th on the Baseball America list). He was promoted to Portland late in the first half of the season (4-5, 6.65).

“Sometimes he struggled last year. I’d love to see him respond to the challenge this year,” Kipper said. “There is a lot to like. He’s got power stuff. He’s a great worker. The other day, he touched 96 and averaged 93. Explosive life to the fastball. Has a new grip for the two-season fastball that has allowed him to created a truer two-seam sink.

“He has a powerful slider. He has his curveball working well. His change-up, like last year, is a work in progress.”

Wilson was a second-round draft pick out of Texas A&M in 2009. He projects to be a reliever, although the Red Sox will keep him stretched out for now.

• Stephen Fife, 24, is the only starter who pitched all last season in Portland. He was an Eastern League All-Star pick after a strong first half (6-2, 3.58). He faded a little, ending up 8-6 with a 4.75.

“He was a good pitcher for a while. Had one heck of a month of June,” Kipper said. “He began the year before injured, so he was really, truly going through first full year of professional baseball, and he did it at the Eastern League level.

“He has a two-seam fastball that, on any given night, really plays well in the lower half of the strike zone and induces ground ball. A change-up that’s developing. This spring training, he has his curveball working really well.”

Fife was a third round draft choice in 2008, out of the University of Utah. Like Pimentel and Wilson, he participated in the exclusive Red Sox rookie camp in the off-season.

• Brock Huntzinger, 22, shows good control with 67 walks in 260 innings the past two season. He is 6-3, 200 pounds.

“A guy that on any given night, can really showcase pretty impressive command of the fastball on both sides of the plate,” Kipper said. “His fastball is clearly his best pitch. Fairly good feel for a change-up and an improving slider.”

Huntzinger was a 2007 third-round draft pick out of Pendleton Heights High School in Indiana. He was 7-8 for Salem last year with a 4.14 ERA.

• Mike Lee, 24, gets attention immediately as a 6-foot-7, 220 pound pitcher. He has 93 strikeouts in 112 innings in Salem last year.

“When he puts his delivery together, he really angles the ball well,” Kipper said. “He’s got a steep angle to the strike zone. He has three pitches: a fastball — both four-seam and two-seam — a slider, and a change-up.

“He’s a very interesting young man because he’s got a body you can’t teach. You can’t teach legs and arms. When he puts it all together, he’s pretty impressive.”

Lee was an eighth-round draft pick out of Oklahoma City University in 2008. He recorded a 9-7 record and 4.42 ERA in Salem last year.

Kipper believes this rotation can be successful. He knows there will be failures, and that’s where his job comes in.

“We learn from those bumps in the road,” he said.

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