The first half of the Red Sox season proved to be a bumpier ride than just about anyone could have predicted, leaving Boston in an uncertain situation as the trade deadline approaches at the end of July. With Tuesday’s All-Star Game now in the past and the second half of the season (along with the 2015 offseason) now staring the Red Sox square in the face, here is a look at the five most pressing questions facing Boston in the season’s final couple months.

1. Will the team extend Jon Lester?

Lester’s situation and the club’s reluctance to give the left-hander a respectable offer have been well-documented throughout the 2014 campaign. There is no denying that Lester is pitching about as well as he ever has—his current 4.2 WAR is second among all qualified starters and his 2.65 ERA and 2.61 FIP would represent career bests—so Boston’s reluctance to commit to the lefty long-term is a little puzzling. Sure, they don’t want to be burned by an expensive contract for a pitcher in his early 30s, but Lester has made legitimate improvements over the past year, and his success is no fluke. He has also made clear that he wants to remain in Boston. It makes too much sense for the Red Sox to re-sign Lester (can you imagine the club’s rotation without him?), and even if the negotiations bleed into free agency this winter, I still expect Ben Cherington to pony up and bring back Lester on a deal that suits both sides.

Will 2014 be Jon Lester's final year in Boston? (Photo credit Kelly O'Connor of

Will 2014 be Jon Lester’s final year in Boston? (Photo credit Kelly O’Connor of

2. Who is coming and going at the trade deadline?

The Red Sox sit in an odd position as the trade deadline approaches. While the club has yet to expressly give up on this season, the writing is on the wall with the team 9.5 games back in the AL East and the offense continuing to sputter. Who Boston ends up dealing at the deadline (and what they get in return) will have a lot to say about where the organization is headed for 2015 and beyond. With Pawtucket’s squad overflowing with talent, the Red Sox don’t necessarily need more upper-level prospects. A major league-ready bat (or two) is needed, and while that might not come until the offseason, Cherington will surely dump a few of the team’s veterans to make room on the roster for other players. Don’t expect a fire sale, yet don’t be surprised to see more than a few names leave town come July 31.

3. What will Boston do with John Lackey?

John Lackey’s future with the Red Sox has flown under the radar with all the hubbub surrounding Lester’s contract situation. Lackey is set to make the veteran’s minimum in 2015, and although Boston is within its rights to keep him on that salary, it’s not the best message to send to a veteran who busted his tail rehabbing from Tommy John surgery and was an essential part of last year’s World Series squad. The right-hander would be an attractive addition for any contending club, but if the Red Sox want to keep him, a two-year extension through 2016 (when Lackey turns 37) could be a solid alternative for both parties.

4. How will the Red Sox handle playing time dilemmas?

The Red Sox are still trying to win this year, but John Farrell has stated that youngsters already on the MLB roster will begin to get more opportunities. We’ve started to see that with the arrivals of Mookie Betts and Christian Vasquez, who should be given the chance to gain as much experience as possible. The same goes for Jackie Bradley Jr., especially as his bat begins to heat up, and the likes of Rubby De La Rosa and Brandon Workman. Getting Xander Bogaerts comfortable at the plate again should be another top priority, with youth likely to play a starring role for the Red Sox in the season’s final months.

5. Who else will get the call from the minors?

Directly related to the previous question is who else might the Red Sox call up from Pawtucket before the season ends. Anthony Ranaudo is making mincemeat of Triple-A lineups, and although his future ceiling remains that of a back-of-the-rotation starter, it’s fair to wonder how much more he can learn with the PawSox. The same goes for Allen Webster, who now has 220 innings of Triple-A experience under his belt and has begun to show some signs of improved command. Garin Cecchini is another candidate to be called up (especially if Boston deals Stephen Drew and slides Bogaerts back to shortstop). Either way, the Red Sox will likely begin giving some of these prospects a closer look at the big league level, with an eye towards them becoming legitimate contributors in 2015.