Ignore for a moment the public posturing about talks being on hold and consider these reasons why Jon Lester will agree to a contract extension with the Red Sox before the end of this season — perhaps before the end of this month.
This list is based on recent conversations with people involved in the situation.
1. Lester still wants to stay in Boston: The lefthander would have preferred getting a deal done in spring training, but that hasn’t changed his stance about wanting to stay with the Red Sox. Every comment he has made about the situation has been measured, on-message, and positive about the Red Sox. What ultimately matters in these situations is what the player wants and Lester still wants to stay.
2. This is getting to be bad business for the Red Sox: Lester has a 2.73 earned average, a 1.15 WHIP, a 2.75 FIP and a 146 ERA-plus. He’s having the best season of his career and every great start raises the price a little and adds to whispers from friends telling him he could get $150 million on the market. Lester made the All-Star team and Justin Masterson, Max Scherzer, and James Shields didn’t. The All-Star team isn’t always an indication of much, but it is this time. Lester is having his best year at the best time.
3. The Red Sox desperately need some good news: This season is a wreck and it’s not going to change much. Signing Lester would be an indication the team is stable and the right steps are being taken to be contenders next season. The longer Lester stays in limbo, the worse it looks. It’s better to be a lousy team going in the right direction than a lousy team with no idea who will start on Opening Day in 2015.
4. CC Sabathia’s career is in trouble: In case you missed the news, Yankees lefthander CC Sabathia is not expected to pitch again this season because of his right knee. Sabathia could need microfracture surgery and that would be career threatening. If Lester becomes a free agent, the Yankees will be first in line with an offer he can’t refuse. This will not be Jacoby Ellsbury going down the street for a contract that is going to look awful in a few years. This will be a powerhouse lefty pitching every five days for your rival and kicking your behind around Fenway Park two or three times a year.
5. Lester is showing he will age well: It’s reasonable to think the Red Sox should be cautious about giving a long-term deal to a 30-year-old with 238 starts and just shy of 1,500 innings under his belt. But Lester is pitching well with a four-seam fastball that is averaging 93 miles per hour, down from the 94-95 he had earlier in his career. How he pitches suggests he will be successful another three or four seasons. If the Sox pay for one subpar season in 2019, that’s the cost of doing business. The Red Sox coaches and baseball operations people believe Lester is a good investment.
6. Lester would be difficult to replace: If the Red Sox are not willing to pay Lester, then they’re certainly not going on the market to pay even more for a free agent ace they don’t know as well. If Lester leaves, here is the rotation for next season: John Lackey ticked off about making the league minimum, Clay Buchholz, and three question marks. Or is that four question marks given Buchholz’s fragile health? It’s great the Red Sox have a bunch of starter prospects and surely a few of them will be good. But there are no guarantees about Brandon Workman, Rubby De La Rosa, Allen Webster, Anthony Ranaudo, Matt Barnes, or even Henry Owens. But a rotation with Lester at the top offers stability and he would be a good role model for the young pitchers.
7. Lester has reasonable people representing him: Sam and Seth Levinson are the same agents who represent Dustin Pedroia. The second baseman signed his extension last July after talks started in spring training. They are agents who make deals, not agents who take their clients to free agency.
The Red Sox made this process more difficult by testing the limits of Lester’s loyalty with a lowball offer of $70 million during spring training. Maybe that was worth a shot, but now is the time to get this done. Lester starts on Thursday and then not again until after the break. That’s seven days to make a deal. It’s something both sides want and the Red Sox need.