When is the best time to sign players to an extention?

[TwinsBrewersWorldSeries]

The Dan Haren thread really got me thinking, and as we approach the point where we want to sign Yo and Parra to an extention (not yet), i've been pondering when the optimal time is.

 

Parra is 25 (finishing year 2)

Gallardo is 22 (finishing year 2)

 

Parra might be a bit older than usual to get established in the bigs (i'd say the typical above average/elite player that we'd want to extend probably breaks in at 21/22, maying them 27/28 in their first season post-arby. With the market majorly overpaying elite talent its almost hopeless for small market teams to get an above average/elite player to sign an extention when they have one year until free agency. Three or four years until free agency, the player is just becoming arbitration eligible and it doesn't make sense to pay the player more especially since they are likely to sign somewhere else post-arby anyways. However, i think 2 years pre-free agency is the optimal time to sign a player (especially a pitcher) to a four year deal.

 

A player with four years of experience typically has been paid their signing bonus, three years of pre-arby money, and a few million their first year of Arby, unless they have an early MONSTER year like Fielder/Howard. These players might be looking at $15/18M per if they wait two more years for free agency, however, with less that $10M, actually less than $5M in most cases, in the bank after their first four years, most players would be smart to lock up $40/50M guaranteed. If they play the arby game, they'd probably make $12-15M in years 5 &6, but if they get hurt, they get nothing. As someone noted in the Dan Haren thread, the difference between $0 and $40M is much bigger than $40M and $60-70M.

 

With this approach, if Yo & Manny have a solid/great years in '09 and '10, i'd offer them both a 4 year deal in Winter 2010 to buy out 2 years of FA. (try to sign for 45-50m deals). Despite Sheets injury issues, would anyone have complained if we had given him (in winter '06) a 2 year/32 million extention for 2009/10? An injury could hamstring a team, but those are the peak years on their arms, and if we don't extend now, there is zero chance they sign a TWO year deal as a free agent. You either sign them 2 years prior to FA, or lose them.

 

I'd also use this approach with JJ Hardy this winter. Hardy has the advantage in that an injury likely would be less career threatening for a position player compared to a pitcher, but JJ probably had a decent but unspectacular signing bonus, $300-400K the past three years, and $2.5m this year. If we keep him through arby, he probably gets $4.5-5M this year and 7-8M in 2010. If we offered him a 4 year/40-45m deal it would be equivalent to a 2 year/$27M extention. $13.5m might be a little high to pay for JJ/season, but if he keeps up a .280/.350/.475 line, he's extremely valuable to this team and would still be very marketable in years 3/4 if we decided to trade him.

 

If Hart is willing to sign a Braunesqe deal, i maybe offer him this offseason, otherwise, wait on Hart/Weeks until next winter and offer them a similar 4 year deal (if Weeks ever turns it around)

[kramnoj]

One thing that should be pointed out is that both Yo and Parra will finish this season with less than 2 years service time, which means they will be under club control through 2013.

 

With the market majorly overpaying elite talent its almost hopeless for small market teams to get an above average/elite player to sign an extention when they have one year until free agency.

 

I don't think you should be mixing up above average and elite. Elite players aren't really majorly overpaid. Above average, even average players, certainly are.

[TwinsBrewersWorldSeries]

When were Yo/Manny brought up last year? Might they qualify as a "super 2" after next season?

[sausage racer]

With Yo only having 2 years in we have to wait and see how a full season after surgery goes for him before throwing more money at him.
I think we need to concentrate on Hart, JJ, and possibly Prince way before those guys.