Hot Stove Beginning To Heat Up?

While MLB’s free agency and trade period is always slower than any of the other four major sports, it has been exceptionally slow this offseason. Everyone who has signed so far, has signed as a minor league free agent, and there haven’t even been any discussions with any of the big name free agents. As for trades, some names and potential destinations have been floated, but nothing serious has come close to happening. That is all expected to change in two weeks when baseball’s winter meetings begin. By then teams will have had their internal discussions and budgets all set up, initial contact will have been made with FA’s and trade partners, and everyone will be in one spot, making deals easier. Before that happens though, we might see one of the biggest names on the trade block on the move. According to the Boston Globe the Red Sox are getting serious in their efforts to acquire Roy Halladay from the Toronto Blue Jays, before the winter meetings.

Halladay would be a huge addition to the Red Sox, giving them three bona fide Aces to headline their staff, but at what cost? Now I’m not talking about the cost in prospects, which is speculated at beginning with pitchers Clay Buchholz and Casey Kelly. I’m talking about what it will cost in money. Strange as it may sound I think the Red Sox can more easily afford to give up two top young pitching prospects, than the huge contract extension that Halladay will require.

Buchholz and Kelly are both nice prospects, but neither should hold up Boston in trading for Halladay. Especially if no other top prospects are included in the deal. Buchholz has been involved in every trade rumor by the Red Sox over the last 4 years. He was once considered to be an ‘ace’ in the making, and has shown plenty of flashes of his potential. While he may no longer be considered a No. 1 starter, he could definitely be a No. 2 for a long time in this league. Even with all his youth and potential, Buchholz is no Roy Halladay. Kelly, who is reported as a potential sticking point, was the Red Sox 1st round pick in 2008 and one of the brightest pitching prospects in the minors. I understand a little reluctance in moving Kelly, but he is an extremely raw pitcher that won’t be in the majors for 2-4 years. Over that time Halladay will have won 15+ games a year, be one of the top pitchers in the league, and likely have led whatever team he’s on (Yankees) to the postseason. Kelly and Buchholz are worth moving for Halladay and what he brings to the table.

In and of itself the $20 million per year Halladay will require isn’t outrageous, and could fit into Boston’s $120 million+ payroll. The problem is that given Boston’s current situation in regards to money on the books it is going to take some creative accounting to fit Halladay in. According to Cot’s Baseball Contracts the Red Sox have $109 million tied up for next season, and that’s not counting any of the arbitration cases or league minimum players, which will add at least $15 million and potentially as much as $20 million. Also that figure doesn’t include Jason Bay or his replacement in left field. If they were to resign Bay and add Halladay the Red Sox would add another $30 million+ to their payroll. As much money as the Red Sox have spent over the years, they have never spent more than $143 million on payroll. This would put them more than $12 million over that previous high, and that’s without signing any other additional free agents.

The truth of the matter is that this year isn’t even the Red Sox biggest problem. Next year things get even tricker for Boston. Any Halladay extension is going to be in the neighborhood of $20 million a year, and a Bay deal will probably be around $16 million a year. Which seems to be fine since they only have $50 million committed next season, and David Ortiz and Mike Lowell are coming off the books. That’s a deceiving figure, because again it doesn’t take into consideration any of this year’s arbitration cases (which will only be larger), new cases (which will jump from $400K, to a couple of million), and Jonathan Papelbon who’s contract could be worth $10-12 million. That $50 million figure (or $86 million with Halladay and Bay) will jump by well over $30 million for all the arbitration cases. Which puts Boston at a very manageable $116 million range, except they have to resign Josh Beckett and Victor Martinez who are both going to be free agent’s after next season. Both will require eight figure per season contracts that could add an additional $25-30 million. The Red Sox will also need to replace Ortiz and Lowell next season in their lineup, and while they can probably find better, and cheaper options, they will still require millions of dollars of payroll.

This seems like a pretty bad payroll crunch to me. I don’t see how Boston can resign Jason Bay if Halladay is acquired, because frankly I don’t know where they will get the money. Yes, the Red Sox are a big market team, but not even them can spend like the Yankees, and not in this economic climate. They don’t have the luxury boxes or sheer number of seats that other stadiums have, to increase their payroll. I think Boston will trade for Halladay, and then find a cheaper option in left field, but this move could very well blow up in their face, if they don’t have the offense to beat New York.